Places to stay in Ashland, OR

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Ashland, OR place to stay
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456 Best places to stay in Ashland, OR

Best family friendly Ashland, OR lodging

Among the 456 accommodations in Ashland, OR, here are the 4 best for families

Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.7 30 reviews

Luxury Ashland Mountain Escape: Pool, Hot Tub

house, Ashland
The Jefferson Estate is situated just a short distance from the charming town of Ashland, in Southern Oregon, offering stunning views of Grizzly Peak from its 8-acre grounds. The property boasts excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
This single-level house comfortably accommodates up to 12 guests in its four bedrooms and four bathrooms. Enjoy the tranquility of the outdoor oasis with a stocked pond, seasonal pool, hot tub, and soothing water feature, along with a fully equipped kitchen for preparing meals and a fireplace for cosy evenings.
Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.8 6 reviews

Luxury Ashland Mountain Escape: Pool, Hot Tub

house, Ashland
This waterfront villa near Ashland, Oregon, is located 1.4 kilometres from Weisinger Family Winery and 4.8 kilometres from Southern Oregon University.
The 353-square-metre property boasts four bedrooms, four bathrooms, and sleeps twelve guests, offering a private pool, hot tub, barbecue grills, and a fully equipped kitchen including a dishwasher; laundry facilities are also provided.
Alice Berry Cottage - Ashland, OR
10 92 reviews

Alice Berry Cottage

house, Ashland
The Alice Berry cottage is located in Ashland's historic railroad district, just a 0.2 kilometre walk from the downtown area, offering easy access to the Ashland Springs Hotel, OSF, Cabaret, Growler Station, coffee shops, restaurants, grocery stores, and parks. The cottage has received excellent user, location and cleanliness ratings.
The cottage is a one-level property with two bedrooms and one bathroom, comfortably accommodating up to four guests. It offers modern amenities such as free Wi-Fi, a Roku TV, an electric fireplace, a private deck, and family-friendly features like a pack and play and a portable highchair.
The Ashland Social | Main House - Ashland, OR
9.8 61 reviews

The Ashland Social | Main House

apartment, Ashland
This comfortable house is located in a quiet residential neighbourhood in Ashland, just a short walk from the Oregon Shakespeare Festival. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house has three bedrooms with king-size beds, two queen-size sofa beds, and four bathrooms, comfortably accommodating up to ten guests. Amenities include a well-equipped kitchen, a private garden, a swimming pool, a hot tub, a sauna, a fitness centre, and a smart TV with access to streaming services.

Best Ashland, OR lodgings with a pool

Among the 456 accommodations in Ashland, OR, here are the 4 best ones with a pool

Lithia Springs Resort - Ashland, OR
No reviews

Lithia Springs Resort

resort, Ashland
Lithia Springs Resort is located in Ashland, Oregon, 4 kilometres from the city centre, offering convenient access to Ashland's attractions.
This hotel boasts a spa, indoor and outdoor swimming pools, a fitness centre, and various business facilities including a conference hall, alongside a bar, library, and picnic area, ensuring a comfortable stay.
The Carriage House, Winner 2025 Best Of Ashland! - Ashland, OR
9.8 294 reviews

The Carriage House, Winner 2025 Best Of Ashland!

apartment, Ashland
This one-bedroom flat is situated in Ashland's Historic Downtown District, just 0.8km from the Oregon Shakespeare Festival, making it perfect for exploring the area's cultural offerings. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The self-catering apartment is located on the upper floor of a garage, offering privacy and a separate space from the main house, and can accommodate up to four guests. The flat includes a fully equipped kitchen, air conditioning, a shared swimming pool, and a garden, perfect for a relaxing stay.
The Ashland Social | Main House - Ashland, OR
10 34 reviews

The Ashland Social | Main House

apartment, Ashland
This luxurious three-bedroom apartment is located just 4 kilometres from the Oregon Shakespeare Festival and the lively Ashland Plaza, offering easy access to the city's cultural attractions and amenities. With an excellent user rating, this property is a popular choice for travellers seeking a comfortable and convenient stay in Ashland.
This spacious apartment spans 282 square metres and comfortably accommodates up to 10 guests. The property includes a fully equipped kitchen, a private outdoor area with a hot tub and seasonal pool, a well-equipped home gym, and a two-person sauna, providing everything you need for a relaxing and enjoyable stay.
The Ashland Social | Entire Estate - Ashland, OR
10 16 reviews

The Ashland Social | Entire Estate

apartment, Ashland
This five-bedroom Ashland house, sleeping up to twelve guests, is conveniently located less than 1.2km from Southern Oregon University and the Schneider Museum of Art, and under 2km from North Mountain Park and the Oregon Cabaret Theatre.
The 282-square-metre property boasts five bathrooms, a private swimming pool, Jacuzzi, sauna, terrace, garden, and fully equipped kitchen; free Wi-Fi and parking are also included.

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! The Oregon Shakespeare Festival is a must, of course, and the historic Lithia Park is beautiful. If you're looking for something a bit further afield, the Rogue River is a short drive away and offers stunning scenery.
  • What are the best accommodations in Ashland, OR?

    Among the accommodations in Ashland, OR, Cozy/rural King Bed, 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 car, as the city is well-connected by Interstate 5. If you're flying, the nearest airport is in Medford, about 20 minutes away. Amtrak also has a station in Ashland, if you're travelling by train.
  • 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 great base for outdoor adventures. Hiking and biking are popular, with trails like the Siskiyou Mountain Loop and the Bear Creek Greenway close by. You can also go fishing, kayaking, or rafting on the Rogue River.
  • 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 summer months, from June to August, when the weather is warm and sunny. This is also when the Oregon Shakespeare Festival is in full swing. If you prefer cooler weather, spring or autumn can be lovely too.
  • 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 great option for a leisurely walk or bike ride. It's a paved path that runs for 16km along Bear Creek, passing through parks, forests, and residential areas. For a more challenging ride, try the Siskiyou Mountain Loop, which offers stunning views of the surrounding mountains.
  • What are the best pet friendly accommodations in Ashland, OR?

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

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

    There are lots of interesting places to visit within a short drive of Ashland. Medford is a larger city with a vibrant downtown area, while Jacksonville is a charming historic town with lots of antique shops and restaurants. For a taste of the rugged beauty of Southern Oregon, head to Crater Lake National Park.
  • What are the best accommodations with parking in Ashland, OR?

    Cozy/rural King Bed, 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 has a wide range of accommodation options, from budget-friendly motels to luxurious hotels. Many places offer amenities like swimming pools, hot tubs, and complimentary breakfast. You'll also find plenty of restaurants, cafes, and shops within walking distance of most hotels.

Popular destinations

Best Ashland, OR accommodations with a garden

The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean - Ashland, OR
9.9 181 reviews

The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean

house, Ashland
This French Country style villa is located on the outskirts of Ashland, offering a peaceful retreat on three acres of land while still being just a short distance from the town's restaurants, shops, and attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The villa is a single-storey property with a floor area of 186 square metres. Amenities include a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, parking, and a rec room with a sofa bed, ensuring a comfortable and enjoyable stay for guests.
Beautiful Guest Suite With Private Deck Overlooking Forest And Waterfall - Ashland, OR
10 97 reviews

Beautiful Guest Suite With Private Deck Overlooking Forest And Waterfall

apartment, Ashland
This one-bedroom apartment is located in Ashland, just 5km from Weisinger Family Winery, Southern Oregon University, and Schneider Museum of Art, making it a convenient base for exploring the city's cultural attractions. It has received excellent user ratings, so you can be sure of a comfortable stay.
The 42 square metre apartment comfortably sleeps two guests and has a fully equipped kitchen, a private patio, and a garden. You'll also enjoy the use of a spa, parking, and free Wi-Fi.
Lodging And Art Gallery-charming Space Next To Everything, Walk Anywhere! - Ashland, OR
9.9 115 reviews

Lodging And Art Gallery-charming Space Next To Everything, Walk Anywhere!

apartment, Ashland
This charming house is located in Ashland's Historic Railroad District, just a kilometre from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house spans 88 square metres and comfortably accommodates up to four guests in one bedroom and one bathroom. Guests can enjoy a fully equipped kitchen, a private garden, a swimming pool, and a terrace, making it an ideal choice for a relaxing and enjoyable stay.
Whimsy On B | 2br Steps To Downtown - Ashland, OR
9.8 10 reviews

Whimsy On B | 2br Steps To Downtown

apartment, Ashland
This flat is situated in Ashland, just a short walk from the Ashland Food Co-op and the town's theatres and cafes.
This property offers accommodation for four guests with two bedrooms, a king-sized bedroom with a TV and a queen bedroom, a living room with a TV, a well-equipped kitchen, and an outdoor space with a porch swing.

Best Ashland, OR accommodations with a kitchen

Swank Suites | Step Free King - Pet Friendly - Ashland, OR
8.8 3 reviews

Swank Suites | Step Free King - Pet Friendly

apartment, Ashland
This first-floor apartment in Ashland's historic Railroad District is situated one block from a grocery store and coffee shop, two blocks from an escape room, and within easy walking distance of downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens.
The 37-square-metre (approximately 398 square feet) flat offers a king-size bed, a kitchenette, a private outdoor lounge, shared laundry facilities, high-speed 5G internet, a 65-inch smart TV with Netflix, and accommodates two guests; parking is also available.
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.
Quiet And Peaceful Cottage Close To Downtown - Ashland, OR
9.8 68 reviews

Quiet And Peaceful Cottage Close To Downtown

apartment, Ashland
This apartment is located in Ashland's Siskiyou-Hargadine Historic District, a mere 500 meters from downtown Ashland, offering convenient access to its shops, restaurants, and cultural attractions.
This 93 square meter, two-storey property accommodates up to five guests, featuring a full kitchen, a pullout sofa bed, a suite with a queen bed, and a private outdoor space, with off-street parking provided.
Chateau Herbe ~Miranda Carriage House Apartment - Ashland, OR
9.5 15 reviews

Chateau Herbe ~Miranda Carriage House Apartment

apartment, Ashland
This two-bedroom apartment, situated within a gated castle community near Interstate 5 and Ashland's city centre, offers easy access to both and boasts stunning mountain views.
The self-catering apartment features a king-size bed and bunk beds, accommodating up to four guests, and includes a kitchen with fridge and microwave, air conditioning, a Jacuzzi, a sauna, parking, and access to classical gardens, orchards, and vineyards within the estate.
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