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Ashland, OR accommodation
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456 Best accommodations in Ashland, OR

Browse Accommodations in the CBD of Ashland, OR

Stay within easy walking distance of the best local bakeries, markets, and squares from central accommodation in Ashland, OR.

Second Spring Property - 3 Bedroom 2 Bath Luxury Home In The Heart Of Ashland - Ashland, OR
9.9 340 reviews

Second Spring Property - 3 Bedroom 2 Bath Luxury Home In The Heart Of Ashland

apartment, Ashland
This smoke-free flat is located in the heart of Ashland's historic downtown district, just a kilometre from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for location, cleanliness and user experience.
The flat is well-equipped with a kitchen including a fridge, freezer, microwave, dishwasher and a washing machine. Relax in the garden, enjoy a game of tennis or take advantage of the spa and the balcony.
Abbott's Cottages- Lark - Ashland, OR
9.9 156 reviews

Abbott's Cottages- Lark

apartment, Ashland
The Lark cottage is located just 0.8 kilometres from the Ashland Plaza, a lively hub with shops, restaurants, and the Oregon Shakespeare Festival, and is set in a tranquil garden setting. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage is a two-bedroom property, comfortably accommodating up to four guests, and offers amenities such as a fully equipped kitchen, a private bathroom, and air conditioning. Guests can enjoy the historic charm of the cottage, originally a 1920s railroad building, and relax in the peaceful garden.
Historic Cottage Close To Plaza - Ashland, OR
9.9 246 reviews

Historic Cottage Close To Plaza

house, Ashland
This one-bedroom cottage is situated in Ashland's Skidmore Historic District, just 0.6 kilometres from the town centre.
The property features a private garden, a fully equipped kitchen, and laundry facilities, making it ideal for a comfortable stay for up to three guests.
Laurel Cottages: Studio + Kitchen Downtown Ashland - Ashland, OR
10 8 reviews

Laurel Cottages: Studio + Kitchen Downtown Ashland

apartment, Ashland
This studio apartment is located in the prime downtown district of Ashland, just a short walk from the Oregon Shakespeare Festival and Lithia Park.
This one-bedroom apartment accommodates two guests and features a fully equipped kitchen, an in-unit washer and dryer, and a shared patio, with Wi-Fi and parking provided.

Best Ashland, OR accommodations with parking

Cowslip's Upper Garden  Suite - Ashland, OR
10 8 reviews

Cowslip's Upper Garden Suite

apartment, Ashland
This self-contained apartment is situated in a quiet Ashland residential neighbourhood, just under 0.5 kilometres from Ashland's city centre and the Oregon Shakespeare Festival.
The one-bedroom flat, sleeping up to three guests, boasts a private deck overlooking a shared garden with a koi pond and waterfall, a kitchen with fridge, freezer and microwave, air conditioning, parking, and access to shared common areas in a historic Craftsman bungalow.
Bluemoon Vacation Rentals - Bluemoon House - Ashland, OR
9.3 4 reviews

Bluemoon Vacation Rentals - Bluemoon House

house, Ashland
Bluemoon House is located in Ashland, a short distance from the Oregon Shakespeare Festival (1.6 kilometres), ScienceWorks Museum (3 kilometres), and Southern Oregon University (3 kilometres).
This five-bedroom house offers spacious accommodation for up to 21 guests, with a fully equipped kitchen, private parking, and a garden, perfect for enjoying the beautiful Oregon weather.
Abbott's Cottages - Cardinal - Ashland, OR
9.8 251 reviews

Abbott's Cottages - Cardinal

bungalow, Ashland
This charming cottage is located in a quiet residential area of Ashland, just a short walk from the town's renowned theatres. It has consistently received excellent ratings for cleanliness, location and overall experience.
The cottage offers one bedroom and one bathroom, sleeping up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, parking and a comfortable outdoor space with a redwood deck, perfect for enjoying a morning coffee.
Charming, Comfortable Garden Studio Above The University. - Ashland, OR
10 22 reviews

Charming, Comfortable Garden Studio Above The University.

studio, Ashland
This studio apartment is located in a backyard neighbourhood just above Southern Oregon University, offering convenient access to downtown Ashland, the Shakespeare Festival, and local restaurants within 2.4 kilometres.
This 36 square metre studio accommodates up to three guests with a queen bed and a futon, featuring a kitchenette with a microwave and fridge, air conditioning, complimentary Wi-Fi, and a flat-screen TV with premium channels, all set within an idyllic garden with an outdoor seating area.

Frequently asked questions about accommodations in Ashland, OR

  • What are the must-see sites in or near Ashland, OR?

    Ashland is packed with things to see! You've got to check out the Oregon Shakespeare Festival, the Lithia Park, and the historic downtown area. If you're up for a drive, the scenic Rogue River and the Crater Lake National Park are both within a couple of hours.
  • What are the best accommodations in Ashland, OR?

    Among the accommodations in Ashland, OR, Cozy/rural Close To Town, Ashland Springs Hotel and Holiday Inn Express Hotel & Suites Ashland By Ihg are the most popular ones.

  • How can travelers reach Ashland, OR?

    The easiest way to get to Ashland is by flying into the Medford Airport (MFR), which is about 20 minutes away. You can also drive there, as it's located right off Interstate 5. If you're feeling adventurous, you can even take the Amtrak train, which stops at the Ashland station.
  • What are the best accommodations with a pool in Ashland, OR?

    Holiday Inn Express Hotel & Suites Ashland By Ihg, Stratford Inn and Ashland Hills Hotel & Suites are the best accommodations with a pool in Ashland, OR.

  • What outdoor activities can visitors enjoy in and around Ashland, OR?

    Ashland is a paradise for outdoor lovers! You can hike the trails in the Siskiyou Mountains, go kayaking on the Rogue River, bike the scenic Bear Creek Greenway, or even go skiing in the nearby mountains during winter. There's something for everyone!
  • What are the best accommodations with a jacuzzi in Ashland, OR?

    The best accommodations with a jacuzzi in Ashland, OR are Holiday Inn Express Hotel & Suites Ashland By Ihg, Stratford Inn and Ashland Hills Hotel & Suites.

  • When is the ideal time to plan a trip to Ashland, OR?

    The best time to visit Ashland is during the spring or autumn, when the weather is mild and the crowds are smaller. If you're a theatre buff, then you'll want to visit during the summer for the Oregon Shakespeare Festival. And if you're a winter sports enthusiast, then you can visit during the winter months for skiing.
  • What are the best accommodations for families and kids in Ashland, OR?

    The best accommodations for families and kids in Ashland, OR are Ashland Springs Hotel, Stratford Inn and Ashland Hills Hotel & Suites.

  • What are the best walking or cycling routes in Ashland, OR?

    The Bear Creek Greenway is a popular choice for walking and cycling, stretching for 16 km through Ashland and beyond. If you're looking for a more challenging hike, try the Lithia Park trail, which winds its way up to the top of the park, offering stunning views of the city.
  • What are the best pet friendly accommodations in Ashland, OR?

    The best pet friendly accommodations in Ashland, OR are Cozy/rural Close To Town, Ashland Springs Hotel and Holiday Inn Express Hotel & Suites Ashland By Ihg.

  • What nearby towns or cities can be explored from Ashland, OR?

    From Ashland, you can easily explore the nearby towns of Jacksonville, a charming historic town with Victorian architecture, and Talent, known for its wineries and craft breweries. If you're looking for a bigger city, Medford is just a short drive away and offers a wider range of amenities and attractions.
  • What are the best accommodations with parking in Ashland, OR?

    Cozy/rural Close To Town, Ashland Springs Hotel and Holiday Inn Express Hotel & Suites Ashland By Ihg are the best accommodations with parking in Ashland, OR.

  • What amenities can travelers expect from accommodations in Ashland, OR?

    Ashland offers a wide range of accommodation options, from budget-friendly motels to luxurious hotels. Most accommodations offer basic amenities like Wi-Fi, parking, and breakfast. Some even have swimming pools, hot tubs, and fitness centres. You'll also find plenty of vacation rentals, from cozy cabins to spacious houses.

Popular destinations

Explore Family Accommodations in Ashland, OR

Give the family plenty of room to stretch out with local parks and sights nearby at family accommodation in Ashland, OR.

Barclay Klum House | Soaking Tub & Gourmet Kitchen - Ashland, OR
9.7 59 reviews

Barclay Klum House | Soaking Tub & Gourmet Kitchen

apartment, Ashland
This Queen Anne-style apartment in Ashland, Oregon, is located less than 1.6 km from Ashland's downtown area, offering easy access to shops, theatres, and parks.
The property, sleeping four guests, boasts a well-equipped kitchen with a European gas stove and electric convection oven, two bedrooms (one queen, one double), a bathroom with a soaking tub and walk-in shower, private off-street parking, and a fenced yard.
Rosewood Landing- Hot Tub & Sauna- Sleeps 10 - Ashland, OR
10 1 review

Rosewood Landing- Hot Tub & Sauna- Sleeps 10

apartment, Medford
This four-bedroom house in Medford is situated a 13-minute walk from Medford City Hall and a 12-minute walk from Medford Carnegie Library.
This 139 square metre property accommodates up to nine guests and features a garden, hot tub, sauna, and on-site parking, with Wi-Fi, air conditioning, a fully equipped kitchen, and laundry facilities provided.
Hanna's House By Wanderlodges - Ashland, OR
9.8 11 reviews

Hanna's House By Wanderlodges

house, Ashland
Hanna's House offers a self-catering property in Ashland, Oregon, conveniently located a short walk from the Oregon Shakespeare Festival and Oregon Cabaret Theatre, and within easy reach of the Schneider Museum of Art (1.9km) and Oak Knoll Golf Course (5.6km).
This 165 square metre house sleeps seven guests and boasts a well-equipped kitchen, private parking, Wi-Fi, a terrace, garden, and air conditioning; nearby activities include fishing, canoeing, hiking, skiing, golfing, and cycling.
Courtside Cottage - Walkscore 93 - Dog Friendly - Ashland, OR
10 339 reviews

Courtside Cottage - Walkscore 93 - Dog Friendly

cottage, Ashland
This charming cottage is situated in Ashland's Historic Railroad District, a mere 0.8 km from the Oregon Shakespeare Festival and the Ashland Library.
The cottage boasts a well-equipped kitchenette with a fridge, freezer, microwave, and dishwasher, perfect for self-catering, and can comfortably accommodate up to four guests.

Best Ashland, OR accommodations with a garden

Charming Guest House - One Block From Downtown! - Ashland, OR
10 674 reviews

Charming Guest House - One Block From Downtown!

house, Ashland
This one-bedroom guest house is located just 0.8 kilometres from the centre of Ashland, a short walk from the Shakespeare Festival, Lithia Park and numerous restaurants and cafes.
The property offers a comfortable living space with a fully equipped kitchen, a spacious bathroom, a private deck and a loft bedroom, accommodating up to four guests.
Manzanita Cottage - Ashland, OR
10 213 reviews

Manzanita Cottage

house, Ashland
This Ashland cottage, situated in the historic railroad district, offers easy walking access to downtown, the Oregon Shakespeare Festival, Lithia Park, and the Ashland Food Coop.
The single-bedroom, single-bathroom property sleeps four, features a well-equipped kitchen with dishwasher, and includes a private entrance, ample on-street parking, and a garden; nearby hiking trails are readily accessible.
The Matriarch Heritage House- Downtown Ashland - Ashland, OR
9.0 4 reviews

The Matriarch Heritage House- Downtown Ashland

house, Ashland
This Ashland dwelling is ideally located in the downtown area, less than 0.25km from the Oregon Shakespeare Festival and 0.5km from the Oregon Cabaret Theatre.
The 149 square metre property boasts two bedrooms, three bathrooms, sleeps six, and includes a fully equipped kitchen, free Wi-Fi, air conditioning, and a private patio.
Private Garden Cottage W Sauna In Rr District - Ashland, OR
9.8 444 reviews

Private Garden Cottage W Sauna In Rr District

house, Ashland
This studio apartment is situated in Ashland's historic Railroad District, a short walk from the Oregon Shakespeare Festival and the town centre.
The self-contained unit sleeps up to four guests and features a sauna, a private deck, and secure bike storage, ideal for exploring the nearby hiking trails.

Best Ashland, OR accommodations with a kitchen

Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly - Ashland, OR
10 71 reviews

Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

apartment, Ashland
Ashland Mid-century With A Yard! - Ashland, OR
10 2 reviews

Ashland Mid-century With A Yard!

apartment, Ashland
Sunset Cottage At Grizzly Peak Winery - Ashland, OR
9.5 11 reviews

Sunset Cottage At Grizzly Peak Winery

house, Ashland
Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment - Ashland, OR
9.4 6 reviews

Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment

apartment, Ashland

Browse Accommodations with a Pool in Ashland, OR

Make a splash under the summer sun or swim peaceful morning laps at accommodation with a pool in Ashland, OR.

The Carriage House, Winner 2025 Best Of Ashland! - Ashland, OR
9.8 289 reviews

The Carriage House, Winner 2025 Best Of Ashland!

apartment, Ashland
The Ashland Social | Guest Studio - Ashland, OR
10 27 reviews

The Ashland Social | Guest Studio

studio, Ashland
Lithia Springs Resort - Ashland, OR
No reviews

Lithia Springs Resort

resort, Ashland
The Ashland Social | Main House - Ashland, OR
10 34 reviews

The Ashland Social | Main House

apartment, Ashland

Your Next Luxury Escape in Ashland, OR

Experience high-end hospitality and immersive local charm at premium accommodation in a historic setting in Ashland, OR.

Green Springs Inn - Ashland, OR
8.7 311 reviews

Green Springs Inn

resort, Ashland

Review Pet-Friendly Accommodations in Ashland, OR

Treat your pup to an unforgettable holiday at pet-friendly accommodation with plenty of walking routes nearby in Ashland, OR.

Bluemoon Vacation Rentals - Bluemoon Cottage - Ashland, OR
9.3 38 reviews

Bluemoon Vacation Rentals - Bluemoon Cottage

apartment, Ashland
Cute Vintage Style Boho Apartment Near Downtown Medford. Convenient To Medical And I-5 Freeway. - Ashland, OR
9.4 8 reviews

Cute Vintage Style Boho Apartment Near Downtown Medford. Convenient To Medical And I-5 Freeway.

apartment, Medford
Paschal Winery - Dream 2 Cottage - Ashland, OR
9.8 53 reviews

Paschal Winery - Dream 2 Cottage

apartment, Talent
Countryman-fox Carriage House - Ashland, OR
10 291 reviews

Countryman-fox Carriage House

house, Ashland
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