15 Towns Similar to Ashland, Oregon

For many people, Ashland remains the jewel of the state of Oregon and a perennial best-kept secret of the Pacific Northwest.

Compared to other Oregon cities like Portland, Eugene, or Salem, Ashland is quite small. With a population of around 20,000 residents, the city has an insular feel that other parts of Oregon lack; in many respects, the city’s sense of coziness is its defining quality.

A Cultured Location

Any discussion of Ashland will likely touch on the city’s legendary Shakespeare festival. Founded in 1935, the Oregon Shakespeare Festival runs from February until October and is centered around a gorgeous Elizabethan-style outdoor pavilion.

The festival attracts hundreds of thousands of visitors to Ashland each year and gives the city a cosmopolitan vibe.

And don’t let the city’s somewhat isolated location in Southern Oregon fool you: The per capita rate of coffee shops and bookstores in Ashland rivals that of Portland.

As the location of Southern Oregon University, moreover, Ashland also has a college town vibe that has been a hit with residents for generations.

Vibrancy Meets Comfort

As you might expect in a city centered around a literary festival, the arts scene in Ashland is intensely vibrant. Here, proximity to art galleries and theaters makes a springtime stroll down the city’s main thoroughfare a real pleasure.

By Oregon standards, Ashland is a fairly costly place to live. You’ll probably meet a lot of wealthy transplants from Portland, Seattle, and San Francisco here. A decent hotel room here will run you around $150 per night.

But staying in Ashland is certainly affordable if you know where to look. Keep an eye out for deals on house rentals during summer and don’t skip the Shakespeare Festival’s off-season if you can do without a bit of theater.

Ashland is certainly a desirable place to visit and certainly a great place to live. So what cities around the United States most resemble this fantastic location?

1. Savannah, Georgia

Perhaps the most beautiful city in the Southern United States, Savannah has long been the cultural hub of Georgia.

Savannah’s elegant mansions and sprawling gardens have made the city famous the world over. It was famously portrayed in the book “Midnight in the Garden of Good and Evil” as well as in the film of the same name. That said, the city is also much larger than Ashland and has a population of nearly 150,000 residents.

2. Harper’s Ferry, West Virginia

Like Ashland, Harper’s Ferry feels like a charming respite from the stress of the modern world. But Ashland seems positively cutting edge in comparison to Harper’s Ferry: The town is home to a minuscule population of around 250 people and looks like something out of a history book.

You’ll find a lot of deals on hotel rooms here; expect to pay around $90 a night for a cozy place to sleep. But keep your eye out for deals!

3. Ann Arbor, Michigan

Like Ashland, Ann Arbor is a leafy college town with a big art scene. Ann Arbor doesn’t have Ashland’s natural resources or hiking trails; however, the city’s quaint Midwestern sensibilities surely make up for its lack of mountain trails and lush countryside.

As one of the most desirable cities in the Midwest, real estate in Ann Arbor can be pricey. But living here is actually a deal compared to major coastal urban centers like San Francisco or New York City.

Although you’ll probably be able to find quality rooms for less, expect to pay around $100 a night for a decent place to stay near the center of the city.

Ann Arbor is best known as the primary campus of the prestigious University of Michigan. The school’s gorgeous architecture veritably defines the town’s New England-like appearance; the University of Michigan Law School features gothic architecture in the style of Oxford University and is particularly beautiful on autumn afternoons.

But it’s Ann Arbor’s arts scene that really makes the city similar to Ashland. As in Ashland, you’ll have your pick of theatrical events to attend, and the city’s Literati Bookstore is the unofficial hub of Ann Arbor’s literary scene. At Literati, you can grab a coffee and check out a literary reading most days of the week.

4. Nantucket, Massachusetts

For a traditional island town styled in true New England fashion, Nantucket is surprisingly cosmopolitan. The town’s homey-but-cultured vibe matches Ashland closely;

both have relatively small populations and large tourist influxes at peak times of the year.

However, Nantucket’s island locale is very different from the mountainous region of Southern Oregon that Ashland occupies.

Tourists with money to burn tend to flock to nearby Martha’s Vineyard, but Nantucket has everything that travelers need: Here, streets filled with cozy cafes and restaurants give way to gorgeous colonial homes and stunning ocean views.

As one of New England’s most aristocratic haunts, it is true that Nantucket can get a bit pricey; hotel rooms here can cost several hundred dollars per night on average. But a stay here is definitely worth the cost.

5. Cambridge, Massachusetts

Home to Harvard University and MIT, Cambridge is another quintessential New England town. Just over the Charles River from Boston, Cambridge is home to some of the most desirable real estate in Massachusetts. Cambridge’s population is much smaller than Boston’s; however, Cambridge feels more like a series of neighborhoods within Boston proper.

It’s easy to spend a lot on hotel rooms in Cambridge; however, you’ll find great deals on quality places to stay around the $125 range.

Cambridge is a slice of Americana at its best. A walk through Harvard Yard on a summer evening can feel like a stroll into another age. This is a place that everyone should visit at least once.

6. Carmel-by-the-Sea, California

Carmel-by-the-Sea is smaller and more costly than Ashland, but its picturesque surroundings make it similar to its northern neighbor. Less than 4,000 people live here permanently, but visitors should expect to see sizable crowds on weekends.

This is without question one of the most beautiful towns in the United States; hotel rooms are priced accordingly. As always, keep your eye out for deals and plan out your trip months before you visit: A good room here will cost around $150 a night; however, a search for deals can yield good results.

7. Olympia, Washington

Often overshadowed by its neighbor Seattle, Olympia is nonetheless a charming small city of about 50,000 residents close to plenty of natural reserves and beautiful scenery.

Like Ashland, Olympia is a sleepy place even by West Coast standards; however, its out-of-the-way character makes it a desirable spot for people keen to experience the wonders of the Pacific Northwest.

There are plenty of cafes and bookshops here thanks to a cultural scene blossoming around the leafy campus of Evergreen State College; as Washington’s state capital, Olympia’s biggest employer is the state government. Olympia also has a vibrant music scene that was once home to no less a performer than Nirvana’s Kurt Cobain.

Despite its small size, the city’s proximity to tech-obsessed Seattle makes it a relatively expensive place to visit: $150 will get you a quality room for the night in Olympia; however, you can find great deals on rooms that don’t cost as much here if you plan out your trip well in advance.

8. Missoula, Montana

Still very much a college town, Missoula resembles Ashland in a number of ways. Great cafes and restaurants are everywhere here, and visitors always get a kick out of Missoula’s extensive natural beauty and snow-capped peaks. For people who love the outdoors, a visit to Missoula is a must.

With a population of nearly 75,000 people, Missoula is considerably larger than Ashland. But its basic vibe is the same: Like Ashland, the fresh air here alone is worth the trip. And that is to say nothing about opportunities for fishing, golfing, or skiing.

In recent years, Missoula has seen its real estate prices skyrocket. But you can still find deals on house rentals within the city limits. Hotels can get as expensive as you please; however, you’ll find a lot of deals around the $130-per-night range.

9. Newport, Rhode Island

Like Ashland, Newport is an intellectually stimulating environment that throws big-city pretensions to the wayside. With a population of around 25,000 residents, Newport seems bigger in summer due to the region’s status as a bonafide tourist draw.

This is a seaside resort in every sense of the word: Expect to see big crowds in warmer months as New Englander’s retreat from hot temperatures in cities like Boston and Providence.

Newport was once the summer preserve of the wealthiest industrialists in the United States, and houses built by families like the Vanderbilts still grace the town’s most exclusive neighborhoods. But most of these mansions are now museums.

Newport isn’t known for being cheap; however, there are definitely deals to be had on hotel rooms here. You’ll probably be able to find a cozy room in Newport for around $120 a night. But keep an eye out for deals on home rentals. These are a great way to see Newport from a unique perspective.

10. Asheville, North Carolina

If tree-lined streets and charming cafes are your things, you’ll probably love Asheville, North Carolina. This is surely one of the most charming locales in the Southern United States, and travelers seemingly always get a kick out of Asheville’s wonderful food scene and vibrant arts community.

Like Ashland, Asheville is a great place to commune with the natural world. Close to plenty of wildlife reserves and sprawling parks, the city is certainly famous for its lush natural surroundings. But Asheville’s Southern vibe is a lot more laid-back than even the quiet environs of Ashland.

And Asheville’s population is far larger than Ashland’s: Nearly 100,000 residents call Asheville home.

Expect to find real deals on hotel rooms here: It’s easy to pay around $100 per night for a good place to stay in Asheville; as with many other desirable locations, however, searching out deals can sometimes produce remarkable results.

11. Park City, Utah

Home to the Sundance Film Festival, tiny Park City really packs a punch. If you love to hike or ski, it is hard to go wrong with a visit here. The population is small in Park City: Permanent residents within the town limits number around 8,375.

But ski season is big business in Park City. And this is to say nothing of the time when the Sundance festival is in full swing. Plan your trip well in advance if you want to get a great deal on a hotel room: A decent place to stay for the night can run for as much as $200. But good deals can be found!

12. Bend, Oregon

Bend isn’t all that far from Ashland relatively speaking; however, the city’s high desert climate makes a visit to Bend a strikingly different experience. In many respects, Bend is a sister city to Ashland and shares its sibling’s thriving arts culture.

Bend is the de facto capital of Oregon’s outdoor sports scene and the city’s economy veritably revolves around outdoor activities. Bend’s proximity to snowy ski runs and challenging natural climbing walls make it a perfect place for people who love getting out into nature.

Like the rest of Oregon, Bend is currently experiencing a steep increase in real estate prices. And its dry climate certainly makes a visit here a different experience to that of Ashland.

On the other hand, if you keep an eye out for good deals on rooms, you’ll likely find a bargain; with a population of less than 100,000, Bend isn’t a big city on par with Portland, and visitors can find great places to stay for cheap.

You’ll probably find rooms that cost as little as $50 a night here; however, expect to pay a bit more for a place with amenities and a central location.

13. St. Francisville, Louisiana

Tucked away in a gorgeous sprawl of lush Louisiana countryside, St. Francisville is smaller than Ashland but has a similar amount of local charm. The community here is tight-knit but extremely friendly and accommodating. Mild temperatures in winter make this a great retreat for people traveling in January and February.

With a population of less than 2,000, St. Francisville lacks the amenities of Ashland or Ann Arbor. But a visit here is a wondrous experience; moreover, accommodations are usually very reasonable. Expect to pay around $80 for a good hotel room when you stay here. That price doesn’t necessarily preclude a crawfish fry-up for dinner!

14. Sun Valley, Idaho

Once the domain of famous writers and railroad magnates, Sun Valley is still one of the fanciest towns west of the Mississippi. But its cultural amenities make it worth the trip to this isolated area within Idaho.

Sun Valley is even tinier than Ashland and has a population of fewer than 2,000 residents. However, the town’s snowy environs and cozy hotels make it popular with visitors and make the area seem bigger and more cosmopolitan than it really is.

Expect to pay around $140 per night for a room here. Prices can certainly get much higher in Sun Valley, but visitors planning out a trip in advance can usually find great deals on charming rooms.

15. Port Townsend, Washington

Port Townsend isn’t that far from Seattle; however, its small coastal village charms are worlds away from Seattle’s big city stressors. Like Ashland, Port Townsend is prized by residents of the Pacific Northwest as a great place to retire.

But Port Townsend still retains fun artistic energy that keeps visitors coming back year after year. Hotels here are surprisingly affordable; good rooms can be had for around $130 a night. And the seafood here is on another level!