America’s Most Expensive Small Towns Offer a Charming Escape

Living in a big city is always harder on the wallet, so we seek out the smaller American towns when we're looking to save a few dollars. That's the logical assumption, anyway, but believe it or not, many of America's small towns and cities are among the most expensive places in the world.

People are drawn to small towns because of their community feel, access to nature, quiet neighborhoods, restaurants, arts and culture — besides, many small towns are typically short drives from major metropolises and all the amenities and conveniences those provide. Some of the towns on this list aren't surprising (we’re looking at you Jackson, Wyoming), but others may come as a shock — like the two towns in Idaho or the several along the Oregon coast.

Are you ready to explore America’s most expensive small towns with populations of 50,000 or fewer? Keep reading to see what makes them worth the splurge.

40. Spirit Lake, Iowa

Population: 17,127

Median home value: $194,300

Where to stay: The Oakwood Inn

*Using data from the U.S. Census Bureau, LendingTree identified the most expensive small towns in America by evaluating home values.

Why Spirit Lake Is Worth the Splurge

You've probably never heard of this small Iowa town, but locals don't seem to mind being out of the public eye. In fact, they probably revel in it, as it affords them the peacefulness the town is known for. 

Life in Spirit Lake revolves around the lakes that surround the town, like East Okoboji Lake and Big Spirit Lake, where you'll find Orleans Beach. In summer, the whole town seems to come to this beach to cool off with fun water activities. At night — no matter the season — the thing to do is enjoy a local craft beer at Okoboji Brewing Company.

39. Riverton, Wyoming

Population: 39,812

Median home value: $196,400

Where to stay: Remodeled historic cabin

Why Riverton Is Worth the Splurge

Nicknamed "the Rendezvous City" for being at the meeting point of the Big and Little Wind rivers, Riverton is quite a special place. Sure, it can't compete with the glitz and glamour of Jackson (more on it later), but it is a common stop for those driving through Wyoming on their way to Grand Teton National Park. 

The Wind River Heritage Center is one of the most popular things to visit, drawing in both residents and visitors with its life-sized historic wax figures and Old West farm equipment. For an otherworldly outdoors experience, head to Castle Gardens Petroglyph Site, where you'll see curious rock formations swirling up to the sky. If you're looking for something just as thrilling but less active, pay a visit to the Wind River Casino. And absolutely no one should miss attending a rodeo show while in town.

38. Vernal, Utah

Population: 36,084

Median home value: $197,000

Where to stay: The Honeybee Inn

Why Vernal Is Worth the Splurge

Aspiring paleontologists should not skip a visit to Vernal, which boasts the nickname of "Dinosaurland." And no, it's not because it's home to a kitschy roadside attraction but because it is extremely wealthy in dinosaur fossils. In fact, the town is a gateway into Dinosaur National Monument. Besides fossils, you'll find petroglyphs carved onto the rock face.

Located in high desert on the Colorado Plateau, visitors should definitely come prepared for outdoor exploration more than modern entertainment. Another nearby cool place to visit is the Flaming Gorge National Recreation Area. There are plenty of ways to explore the gorge, including rafting and hiking.

37. Fort Morgan, Colorado

Population: 28,517

Median home value: $201,200

Where to stay: Best Western Plus Overland Inn

Why Fort Morgan Is Worth the Splurge

Fort Morgan boasts being one of the places famous musician Glenn Miller lived as a teen. If you're "In the Mood" for a "Moonlight Serenade," you'll definitely find that here. 

But even if you're unfortunate enough to not appreciate Glenn Miller, you'll find plenty of cool things to do in Fort Morgan, particularly in the Great Outdoors. We recommend not even thinking about skipping the Pawnee Pioneer Trail Scenic and Historic Byway, which will take you through the towering Pawnee Buttes and the Colorado Piedmont as well as the Pawnee National Grasslands. On the way, you may encounter desert wildlife like coyotes and rattlesnakes. For a less dry landscape, you can have fun at Jackson Lake State Park.

Another must-see landmark to see while in town is the Rainbow Bridge. One of the last remaining Marsh Arch Bridges, it is now officially part of the National Register of Historic Places.

36. Susanville, California

Population: 30,818

Median home value: $203,000

Where to stay: Spanish revival home

Why Susanville Is Worth the Splurge

Once a mining and logging town, Susanville is a cool place to visit if you're curious about California's settlement history. Most of the attractions in town center around this legacy as well as the vast nature that dominates its surroundings. 

If you want to know more about lumbering, you can visit the Lassen Historical Museums, which preserve artifacts and cabins from the mid-1800s. You can also get outdoors at Susanville Ranch Park, which has 1,100 acres dedicated to providing the locals with green space. But the absolute best thing to do here is the Bizz Johnson National Recreation Trail. The unique trail follows two former lines of the Southern Pacific Railroad, so you'll get nature with a side of history.

35. Red Wing, Minnesota

Population: 46,246

Median home value: $204,100

Where to stay: St. James Hotel

Why Red Wing Is Worth the Splurge

Straddling the line between small town and big city, Red Wing manages to have the best of both worlds: an intimate community and access to nature as well as tons of fun things to do.

Following the mighty Mississippi River, the town exudes charm with the historical homes that line its downtown. It is also here that you'll find many of the most fun things to do, including catching a show at the Sheldon Theatre of Performing Arts. After the show, you can get a local brew and pizza at the Red Wing Brewery. If you don't mind getting out of town, spend the day sipping wine at the Falconer Vineyards.

As in other small towns, locals here absolutely love the outdoors, hitting up trails to get to Barn Bluff, Red Wing's most iconic landmark. 

34. Rock Springs, Wyoming

Population: 43,521

Median home value: $205,600

Where to stay: Homewood Suites by Hilton Rock Springs

Why Rock Springs Is Worth the Splurge

Rock Springs has everything you could expect from a cute Wyoming small town: a historic downtown, a strong rodeo culture and some out-of-this-world nature. 

Downtown is the perfect place to go boutique shopping or to support the local economy by dining at family-owned restaurants that cook like no one else can. As for rodeos, small ones happen throughout the year, but there are also some big events, like the Sweetwater County Fair and Rodeo, that take place in Rock Springs. 

But great as those two things are, they pale in comparison to the amazing Killpecker Sand Dunes just outside of town. As the second largest sand dunes in the entire world, they offer some really fun activities, like ATV driving through the arid landscape in order to see things like petroglyphs and the core of an extinct volcano.

33. Bennington, Vermont

Population: 35,746

Median home value: $207,600

Where to stay: Four Chimneys Inn

Why Bennington Is Worth the Splurge

The quintessential small Vermont town, Bennington has plenty of historic buildings, delicious local restaurants and easy access to nature. What it has over other places in the state, however, is relative proximity to three major cities: New York, Boston and Albany. The first two are three hours away, while it'll only take you an hour to get to the capital of New York state.

Located on the Appalachian Trail and near Lake Shaftsbury State Park, nature is always at your fingertips. Of course, fall foliage is next level, making autumn the best season to visit Bennington and walk around its historic old town. Landmarks to visit include Robert Frost's grave, the whitewashed Old First Church and the Bennington Battle Monument, which is the tallest structure in Vermont. 

Of course, putting maple syrup into as many foods as possible is an absolute must.

32. Spearfish, South Dakota

Population: 25,478

Median home value: $207,900

Where to stay: 1890s log cabin

Why Spearfish Is Worth the Splurge

Nestled at the foot of the majestic Black Hills National Forest, Spearfish is a perfect destination for outdoors enthusiasts. In fact, nature is the No. 1 reason to visit this town, which also has a fair amount of historic buildings to boast about. 

In town, you can learn about pioneer history at the High Plains Western Heritage Center or drive to the edge to visit Frawley Ranch, South Dakota's largest farm. But once you've checked that off the list, don't waste time getting into the northern Black Hills and Spearfish Canyon. Activities abound — hiking, fishing, swimming (depending on the time of year), canoeing and picnicking are all possible. There are also numerous waterfalls in the area, which make for a particularly rewarding hike.

31. The Dalles, Oregon

Population: 26,130

Median home value: $212,900

Where to stay: R&R Guest House

Why The Dalles Is Worth the Splurge

Besides its curious name, The Dalles is known for being a historically important point on the Oregon Trail. Fur trappers and immigrants passed through here, using its position along the Columbia River to send things up north. 

Though you won't find fur trappers here anymore, you can still enjoy the pretty scenery of the Columbia River and learn about Oregonian history. You can also take advantage of the state's underrated wine scene at the Sunshine Mill Winery or with a wine tour of other nearby vineyards.

30. Alexandria, Minnesota

Population: 37,513

Median home value: $214,800

Where to stay: Arrowwood Resort & Conference Center

Why Alexandria Is Worth the Splurge

If you love lakes, then you'll certainly want to make plans to visit Alexandria, which boasts no less than 350 lakes in its area. As you can imagine, this means that lake activities are the soul of the town, and it is probably impossible to find a local who isn't into fishing and boating. 

Outside the lakes, the area is also surrounded by wineries and has a whiskey distillery, so you'll definitely have opportunities to relax while enjoying great drinks. The other thing that makes the town stand out is its claim that Vikings arrived during the Middle Ages and explored the area. While the claim is heavily disputed and dismissed by most historians, this hasn't stopped the people from making Vikings a common motif around town.

29. Pullman, Washington

Population: 49,231

Median home value: $217,600

Where to stay: Coast Hilltop Inn

Why Pullman Is Worth the Splurge

Though largely agricultural, Pullman exudes a mid-sized city vibe thanks to it being the home of Washington State University. The institution guarantees that the local population is young and that research and innovation are a big part of the culture here. 

It should be no surprise, then, that you can find several museums around town, like the Charles R. Conner Museum, the Palouse Discovery Science Center and the Museum of Anthropology. For more active pursuits, you can head to a golf course, enjoy views of the quite literally rolling fields or get some outdoor time at Wawawai County Park.

28. Crescent City, California

Population: 27,495

Median home value: $218,800

Where to stay: Renovated beach house

Why Crescent City Is Worth the Splurge

Leave it to California to have expensive yet infinitely amazing small towns. Located right on the Pacific Ocean, Crescent City is named because of the shape of its sandy beach. If crowds and noise don't sound like the kind of beach vacation that you want, you'll love the perfect quiet and peacefulness of this town. 

As if being an idyllic beach town wasn't enough, Crescent City is also right next to Redwood National and State parks, where you'll find some of the country's most magnificent forest landscapes. You'll spend most of your time between the beach and the forest, but you can also enjoy some fresh seafood, go boutique shopping and visit the picturesque Battery Point Lighthouse.

27. Brevard, North Carolina

Population: 33,775

Median home value: $221,900

Where to stay: Ash Grove Mountain Cabins & Camping

Why Brevard Is Worth the Splurge

Mountain bikers talk about Brevard in reverent tones, as the town is one of the best destinations for the activity in the entire country. The title is mostly thanks to it being the gateway into the vast Pisgah National Forest. Hiking is the second most popular activity in town, particularly in the summer, when you can hike to one of the many waterfalls hidden within the forest, some of which offer a chance for a refreshing swim.

Another cool thing to do is to visit Crystal Mountain Gem Mine, where you can learn about the history of mining in the area and actually mine for your own gemstones. Families particularly enjoy this activity, as it's something that entertains people of all ages. Since this is North Carolina and Asheville is not too far away, you can expect a strong microbrewery scene as well.

No matter what you do, be sure to be on the lookout for the unique resident white squirrels.

26. Moscow, Idaho

Population: 39,505

Median home value: $228,200

Where to stay: Moscow Red Cube

Why Moscow Is Worth the Splurge

Nicknamed the "Heart of the Arts," Moscow — Idaho, not Russia — is one of the state's coolest small towns. The town earned the nickname with its numerous festivals, which focus on culture, art and music and which include the Lionel Hampton International Jazz Festival, the Renaissance Fair and Festival Dance. The town also holds an artwalk on the thi^rd Thursday of each month from fall to spring. This event opens up galleries and hosts events that showcase local and national artists. 

Moscow is also virtually surrounded by mountains on all sides, so you'll have plenty of opportunities to fish, bike, ski, kayak, hike, fish and more. In fact, the city is right next to Pullman, Washington, so it's very easy to visit Washington State University as well as the aforementioned museums.

25. Laramie, Wyoming

Population: 38,390

Median home value: $235,000

Where to stay: AmericInn by Wyndham Laramie Near University of Wyoming

Why Laramie Is Worth the Splurge

A quaint college town, Laramie has quickly risen to become one of the best places to live in Wyoming. It offers incredible outdoor recreation in the Snowy Range Mountains and Medicine Bow-Routt National Forest, not to mention its small-town, frontier charm.

Laramie is steeped in history as well, it is home to more than 20 National Register sites and has some of the most important cultural events in the state of Wyoming, like the rodeo, live music and sporting events.

24. Dickinson, North Dakota

Population: 32,003

Median home value: $237,800

Where to stay: Candlewood Suites Dickinson

Why Dickinson Is Worth the Splurge

An oil boom in North Dakota is what put Dickinson on the map. A booming economy and low unemployment rate, as well as manufacturing and agriculture industries, mean this town is thriving, with plenty of job availability. It is also the gateway to Theodore Roosevelt National Park and Dickinson State University.

Outdoor activities are very important to residents as well. You'll be able to find the 144-mile Maah Daah Hey Trail, in addition to ample opportunities for fishing and hiking, biking and horseback riding.

23. Taos, New Mexico

Population: 32,786

Median home value: $239,500

Where to stay: El Pueblo Lodge

Why Taos Is Worth the Splurge

The 400-year-old Taos is a friendly small town known for its heavy arts scene and fabulous outdoor activities. Located at the foot of some of the tallest peaks in the state, you will be spoiled for choice when it comes to activities. Think hot-air ballooning, hiking, river rafting, gallery hopping and fine dining.

You can even visit a Native American pueblo that dates back thousands of years and is still inhabited today. The town is also about 70 miles from Santa Fe, meaning the big-city essentials are never very far.

Though nothing can beat the original, pueblo-style houses are popular in Taos, making for some of the coolest houses in American small towns.

22. Montrose, Colorado

Population: 46,482

Median home value: $240,100

Where to stay: Super 8 by Wyndham Montrose

Why Montrose Is Worth the Splurge

Montrose is a small town located in the remote western part of Colorado. It's about an hour southeast of Grand Junction, not far from the thriving ski resort of Telluride. Montrose is all about the great outdoors, putting residents and visitors at the doorstep of the most gorgeous peaks, thick forests and raging rivers.

It is one of the top places in the world for outdoor activity. But you'll also find great community activities like the farmer's market, museums, great restaurants and breweries. You also will be near Colorado National Monument and Gunnison National Park.

21. Prineville, Oregon

Population: 23,011

Median home value: $246,100

Where to stay: Best Western Prineville

Why Prineville Is Worth the Splurge

Prineville is a city located in the center of Oregon, surrounded by both high desert and thick, forested hills. As a result, outdoor activities are what the area is known for, whether it's hiking or cycling, fishing and beyond.

Historic Downtown Prineville dates back to the 19th century, including the Crook County Courthouse and the building that holds the A.R. Bowman Museum. From Prineville, residents and visitors have direct access to the Lower Crooked River and the Painted Hills. 

20. Williston, North Dakota

Population: 35,208

Median home value: $247,400

Where to stay: Hampton Inn & Suites Williston

Why Williston Is Worth the Splurge

North Dakota may not seem like it has a whole lot going on, but Williston is another small town that proves the stereotype is incorrect. Historic Williston is all about outdoor adventure, dining, shopping, wellness and family-friendly activities. Steeped in pioneer history, Williston pays tribute to explorers like Lewis and Clark and even has a Frontier Museum.

Residents enjoy fishing on the Missouri River, Yellowstone River and Lake Sakakawea as well as exploring Lewis and Clark State Park. The north entrance to Theodore Roosevelt National Park is also located near Williston.

19. Newport, Oregon

Population: 48,547

Median home value: $251,200

Where to stay: Agate Beach Motel

Why Newport Is Worth the Splurge

This funky Oregon coastal town lives and breathes the sea. Chock full of character, the town is home to obscure museums (like the wax museum, undersea gardens and several roadside attractions). It's also a waterfront town with fantastic restaurants, craft breweries, historic lighthouses and the Oregon Coast Aquarium.

You'll also enjoy the beach life at Nye Beach, which has wonderful shops, cafes and hotels as well as the Newport Performing and Visual Arts Centers.

18. Sandpoint, Idaho

Population: 43,611

Median home value: $254,200

Where to stay: Schweitzer Mountain Resort Lodging

Why Sandpoint Is Worth the Splurge

Located on the shores of Lake Pond Oreille, Sandpoint is one of the biggest recreational cities in the nation — for all seasons. Come summer the lakefront is buzzing with swimmers, boaters and sunbathers, while the winters see the slopes of Schweitzer Mountain Resort blanketed in snow.

The Selkirk and Cabinet mountain ranges provide much of the outdoor activity for Sandpoint, while the art scene, shops, restaurants and cultural attractions bring more than 2 million tourists every year.

17. Brookings, Oregon

Population: 22,650

Median home value: $265,400

Where to stay: Beachfront Inn

Why Brookings Is Worth the Splurge

Another coastal Oregon town, Brookings sits in Curry County on the banks of the Chetco River and the Pacific Ocean. While it was founded in the early 20th century as part of the Brookings Lumber and Box Company, today, it is a prime destination for retirees who are seeking outdoor adventure amid the towering redwood trees.

But beyond outdoor amazement, Brookings is also known for its community activities like the Nature's Coast Light Show and Azalea Festivals. There are plenty of state parks nearby, scenic drives, and a bustling dining and brewery scene.

16. Sheridan, Wyoming

Population: 30,140

Median home value: $272,400

Where to stay: Sheridan Inn

Why Sheridan Is Worth the Splurge

Halfway between Yellowstone National Park and Mount Rushmore sits the small city of Sheridan. If you want to get a glimpse at modern frontier living, this is the place to be. After all, it was a prime spot for cowboys and pioneers during the days of the great western migration.

Today, the town is known for its history, nature in Bighorn National Forest, funky restaurants and cafes, and artist galleries. It has a little bit of everything, all surrounded by the natural beauty of the great American plains.

15. Astoria, Oregon

Population: 39,102

Median home value: $283,900

Where to stay: Cannery Pier Hotel & Spa

Why Astoria Is Worth the Splurge

Astoria drips with Pacific Northwest mystery and charm. Bordered by the Columbia River and the Pacific Ocean, Astoria is both naturally beautiful and culturally stimulating. First stop is to visit the Astoria Riverfront, which is home to the fantastic restaurants of the town as well as relics of its history. Downtown has the Oregon Film Museum, art galleries and the Columbia River Maritime Museum.

You can also visit Lewis and Clark National Historical Park as well as Fort Stevens State Park. The town is not far from Portland, either, which means the vitals of the big city are within easy reach.

14. Ellensburg, Washington

Population: 45,897

Median home value: $286,900

Where to stay: Best Western Plus Ellensburg Hotel

Why Ellensburg Is Worth the Splurge

Ellensburg sits tucked in the crook of the Kittitas Valley, surrounded by the towering Cascade Mountains. The 19th-century town is steeped in gorgeous historical architecture, meaning every stroll is packed with visuals. The town is also home to Central Washington University, which breathes vibrance into the town, from the lively cafes and restaurants to the calendar of events.

Visit the Clymer Museum of Art for culture, the many wineries to taste the good stuff, or set out into the many parks and recreational areas to soak up nature.

13. Fredericksburg, Texas

Population: 26,459

Median home value: $286,900

Where to stay: Hangar Hotel

Why Fredericksburg Is Worth the Splurge

The jewel of Texas Hill Country is none other than the town of Fredericksburg, perfectly positioned between Austin and San Antonio. The small town is known for its Wild West vibes that merge with unique German heritage.

Throw in shopping, wineries, museums, and it's easy to see why Fredericksburg is not only a great place to visit, but also one of the more expensive places to live.

12. Kill Devil Hills, North Carolina

Population: 36,222

Median home value: $289,000

Where to stay: TownePlace Suites by Marriott Outer Banks Kill Devil Hills

Why Kill Devil Hills Is Worth the Splurge

Located on the beautiful Outer Banks of North Carolina, Kill Devil Hills is prime beachfront living surrounded by nature and packed with things to do. In fact, Kill Devil Hills is home to the first powered air flights from the Wright Brothers. You can learn all about it at the Wright Brothers National Memorial.

But it's also a town known for its surfing and kayaking, art scenes and family-friendly community activities like playgrounds, go-karts and mini-golf.

11. Ketchikan, Alaska

Population: 13,800

Median home value: $289,900

Where to stay: Inn at Creek Street

Why Ketchikan Is Worth the Splurge

Facing Alaska's famous Inside Passage, Ketchikan is a popular stop for cruise ships heading deeper into the Alaskan wilderness. As you can expect, it is one of the most beautiful places on the planet, home to the Misty Fiords National Monument, waterfalls, rivers, wildlife and centuries of Native American history.

If you like salmon, this may be the spot for you, as it is the self-proclaimed "Salmon Capital of the World." Visit the Tongass National Forest, explore the Potlatch Totem Park or stroll the historic (former red-light-district-turned arts and crafts area) of Creek Street.

10. Los Alamos, New Mexico

Population: 18,625

Median home value: $302,800

Where to stay: Holiday Inn Express Hotel & Suites Los Alamos Entrada Park

Why Los Alamos Is Worth the Splurge

Los Alamos has been somewhat of a famous place for a while. It was the spot where Dr. Oppenheimer worked on the first atomic bond. But, today, it has become quite a popular (and expensive) place to live. This can be attributed to the rich history, craft breweries, outdoor recreation and boutique shopping.

Bandelier National Monument is one of the top draws to Los Alamos — it's a 33,000-acre area of mesa and canyons with evidence of 11,000 years of history. Then, you also have numerous museums, the Pajarito Mountain Ski Area and art galleries to explore.

9. Easton, Maryland

Population: 37,167

Median home value: $336,800

Where to stay: Best Western Plus Easton Inn & Suites

Why Easton Is Worth the Splurge

Long viewed as one of the best vacation towns in the country, Easton enjoys a stunning location along the Atlantic Coast of Maryland. Here you'll find gorgeous American architecture, like the nation's oldest Quaker meeting house built in the 1600s. Culture abounds in Easton as well, from the Avalon Theatre to the Academy Art Museum.

Residents and visitors of Easton also love exploring the 400 acres of the Pickering Creek Audubon Center. You'll also find a buzzing art scene within the many galleries in Easton, along with fine dining, shopping and beautiful, historic homes.

8. Juneau, Alaska

Population: 32,227

Median home value: $345,900

Where to stay: Pearson’s Pond Luxury Suites and Vacation Rentals

Why Juneau Is Worth the Splurge

Juneau is one of the most beautiful cities in the country — and also one of the most difficult to access. It sits on the southern part of Alaska's panhandle and is only accessible by sea or air.

Still, it remains one of the most desirable spots in the country thanks to its natural beauty (glaciers and mountains), busy ship port, Tongass National Forest, modern-day restaurants, art galleries and beautiful homes.

7. Hood River, Oregon

Population: 23,209

Median home value: $373,600

Where to stay: Westcliff Lodge

Why Hood River Is Worth the Splurge

Hood River is a small town surrounded by the stunning natural beauty of Oregon's Columbia River Gorge. Residents and visitors absolutely love all of the outdoor things to do, from scouting waterfalls to hiking the basalt cliffs that overlook the river. Of course, all of this is set against the backdrop of the looming Mt. Hood.

Other things to do include kiteboarding and windsurfing, great restaurants, fabulous wine, and lots of arts and culture. You can even ride the rails along the historic Mount Hood Railroad — a four-hour excursion that runs to Parkdale and back. All of this combines to make Hood River one of the overall best small towns in the U.S.

6. Gardnerville Ranchos, Nevada

Population: 48,132

Median home value: $378,800

Where to stay: Best Western Topaz Lake

Why Gardnerville Ranchos Is Worth the Splurge

South of Carson City, Gardnerville Ranchos is a beautiful town located not far from the Nevada side of Lake Tahoe. As such, you can imagine that it is brimming with wonderful outdoor activities. Lampe Park, for example, spans 32 acres and features recreational fields and sports courts, free for use.

Similarly, the community has Heritage Park Gardens, which is a community garden downtown where visitors and volunteers are able to stroll through and participate in workshops. Horseback riding is big in Gardnerville Ranchos as well. And, of course, let's not forget the easy access to the banks of Lake Tahoe and all the activities that the alpine lake provides year-round.

5. Hailey, Idaho

Population: 23,421

Median home value: $413,700

Where to stay: Wood River Inn & Suites

Why Hailey Is Worth the Splurge

Tucked within the Wood River Valley, Hailey is one of the more scenic spots in the country. Surrounded by the Sawtooth National Forest, the wild region is primed for hiking, horseback riding, cross-country skiing and mountain biking.

Hailey also happens to be near Sun Valley Resort, which is considered to be one of the best skiing locations on the continent. You'll also find rich botanical gardens, history, nature preserves and, of course, great restaurants.

4. Steamboat Springs, Colorado

Population: 25,072

Median home value: $535,300

Where to stay: Nordic Lodge of Steamboat Springs

Why Steamboat Springs Is Worth the Splurge

When looking to explore the very best of Colorado's great outdoors, you can't do much better than Steamboat Springs. Surrounded by the Medicine Bow-Routt National Forests, as well as the towering Mt. Werner, Steamboat Springs is a haven for outdoor activity. The summer sees golfers, hikers and campers, while winter brings world-class skiing.

The town, itself, has splendid restaurants, art galleries, botanical gardens and walking paths. Historic sites also abound, as Steamboat Springs was one of the original mining towns of Colorado.

3. Jackson, Wyoming

Population: 34,706

Median home value: $549,800

Where to stay: Hotel Jackson

Why Jackson Is Worth the Splurge

Tucked at the base of the Teton Mountains, Jackson is a prime location to experience some of the most dramatic scenery in the nation. It's just a short drive to both Yellowstone National Park and Grand Teton National Park as well as the Bridger-Teton National Forest. Keep your eyes peeled for elk, bison and grizzlies.

In town, the vibe exudes 21st-century Old West. You'll see modern-day ranchers having drinks alongside the world's most wealthy. As such, expect fabulous bars and restaurants, museums and even a Wild West show and rodeo.

2. Breckenridge, Colorado

Population: 30,649

Median home value: $579,600

Where to stay: Valdoro Mountain Lodge

Why Breckenridge Is Worth the Splurge

Another one of Colorado's historic mining towns-turned-top travel destinations, Breckenridge is known for its world-renowned skiing, hiking, restaurants and nightlife. Surrounded by five towering peaks, the historic old town has grown to become one of the most beloved in the state of Colorado.

Wander down historic Main Street into the historic buildings that have been turned into modern-day restaurants and galleries, or grab a backpack to hit one of the hundreds of miles of hiking trails. Come winter, Breckenridge Ski Resort becomes the most popular in the southern Tenmile Range.

1. Vineyard Haven, Massachusetts

Population: 17,312

Median home value: $699,500

Where to stay: Mansion House

Why Vineyard Haven Is Worth the Splurge

Hop a ferry from Cape Cod, Massachusetts, and you'll land on Martha's Vineyard — essentially the premiere island getaway for New Englanders. This paradise of an island is known for its sandy beaches, sailing culture, New England cottages, lighthouses, nature and fabulous hotels.

Vineyard Haven started as a small fishing village, but today, it is a prime tourist destination and a great place to live thanks to its charming shops, restaurants and harbor. Even when things get bleak and cold in the winter months, Vineyard Haven's summer reputation makes it one of the most desirable places to live in the world.