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

Savage Upon Siskiyou | Prime Osf Location - Ashland, OR
10 1 review

Savage Upon Siskiyou | Prime Osf Location

house, Ashland
This detached house in Ashland offers a prime location for Oregon Shakespeare Festival attendees, situated a mere 6-minute walk from Ashland Library and 0.8 kilometres from the Oregon Cabaret Theatre, with Southern Oregon University also within a 15-minute walk.
This spacious 186 square metre residence accommodates up to 15 guests with one bedroom and two bathrooms, featuring air conditioning, a private terrace, a garden, a spa, and a fully equipped kitchen including a dishwasher and oven, with Wi-Fi and nearby skiing opportunities.
144 M² Apartment ∙ 3 Bedrooms ∙ 3 Guests - Ashland, OR
No reviews

144 M² Apartment ∙ 3 Bedrooms ∙ 3 Guests

apartment, Ashland
Holiday rental listing for up to 3 people. This accommodation is located in Ashland.
Facilities and services include free parking, air conditioning and a freeze. This apartment also has a garden!
The Aloha House - Hot Tub - Pool - Ashland, OR
9.9 157 reviews

The Aloha House - Hot Tub - Pool

apartment, Ashland
The Aloha House is situated just 2.4 kilometres from the centre of Ashland, offering a tranquil retreat in a wooded setting above the University. This apartment has received excellent ratings for its location, cleanliness, and overall experience.
The Aloha House is a two-bedroom property with two bathrooms, comfortably accommodating up to four guests. This accommodation provides a range of amenities including a swimming pool, hot tub, sauna, and a uniquely designed outdoor living space with a barbecue area.
Rosewood Collective | House & Studio | Sleeps 11! - Ashland, OR
10 1 review

Rosewood Collective | House & Studio | Sleeps 11!

studio, Medford
This studio apartment is located in Medford's city centre, offering convenient access to Alba Park and Bear Creek Park, and is close to attractions such as the Children's Museum and The RRRink.
This pet-friendly accommodation for up to 11 guests features a private patio, shared access to a hot tub and grill, and private parking, with air conditioning and Wi-Fi provided for comfort.

Best Ashland, OR lodgings with a pool

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

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

The Ashland Social | Guest Studio

studio, Ashland
This studio apartment is located just 0.4 kilometres from Ashland Plaza, placing you within easy reach of the city's main attractions, restaurants, and shops. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has a private entrance and can comfortably accommodate two guests. It features a kitchenette with a fridge, microwave, and other appliances, as well as Wi-Fi, heating, and parking.
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.
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
9.8 289 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.

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

Charming House Two Blocks From Downtown Ashland - Ashland, OR
9.6 11 reviews

Charming House Two Blocks From Downtown Ashland

apartment, Ashland
The Serendipity House, a newly remodelled two-bedroom property, is centrally located in Ashland, Oregon, just 0.32 kilometres from restaurants, shops, and theatres, offering easy access to the Oregon Cabaret Theatre and Allen Elizabethan Theatre.
This self-catering house sleeps four guests and boasts a full kitchen with complimentary coffee, a spacious living room, a private garden, parking, and air conditioning, plus it's ideally situated for exploring North Mountain Park and the Rogue River-Siskiyou National Forest.
Hanna`s House | Downtown Retreat, Steps To Osf - Ashland, OR
10 170 reviews

Hanna`s House | Downtown Retreat, Steps To Osf

apartment, Ashland
Hanna's House, a centrally located dwelling in Ashland's historic district, is a short walk from the Oregon Shakespeare Festival, the Oregon Cabaret Theatre, and Ashland Public Library.
This 165-square-metre (1776 sq ft) property features one bedroom, one bathroom, and sleeps four guests, offering a full kitchen, private garden, spa, parking, and air conditioning.
Refurbished Barn On Acerage Just Outside Ashland - Ashland, OR
9.8 11 reviews

Refurbished Barn On Acerage Just Outside Ashland

apartment, Ashland
This refurbished barn, offering a country escape on six acres, is located just 7 minutes by car from downtown Ashland and 10 minutes from Lithia Park and the Oregon Shakespeare Festival.
This three-bedroom, one-and-a-half bathroom dwelling accommodates six guests and features a jacuzzi, garden, and parking, with opportunities for hiking, wine tasting, and day trips to Crater Lake.
Kellys Carriage House 4 Miles From Ashland - Ashland, OR
9.9 376 reviews

Kellys Carriage House 4 Miles From Ashland

gîte, Talent
The Carriage House gîte is situated on Kelly's Farm, Talent, Oregon, 6.4km from Ashland, offering easy access to Highway 5.
This pet-friendly self-catering cottage sleeps three, boasting a Harry Potter-themed bedroom, a fully equipped kitchen with a smart oven and propane grill, stunning mountain views, and on-site farm animals.

Best Ashland, OR accommodations with a kitchen

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

Countryman-fox Carriage House

house, Ashland
This Ashland cottage, situated directly opposite the Cabaret Theatre and within easy walking distance of Lithia Park, the Oregon Shakespeare Festival, and the town centre, offers excellent access to Ashland's cultural attractions. The property boasts a king-size bed, fireplace, one bathroom, a fenced yard, electric vehicle charging, and accommodates two guests, with modern amenities including a dishwasher and air conditioning.
Grandview Of Ashland | Hot Tub | Sauna | Firepit - Ashland, OR
9.9 36 reviews

Grandview Of Ashland | Hot Tub | Sauna | Firepit

apartment, Ashland
This modern house in the Ashland hills is a short drive (distance to be specified in km) from Ashland's town centre and Oregon Shakespeare Festival, and similarly close to Lithia Park.
Sleeping up to six guests, this two-bedroom property boasts a gourmet kitchen with wine fridge, a hot tub, sauna, and outdoor fire pit, alongside a fitness centre and parking.
Luxury Condo With King Bedroom, Two Bathrooms, Full Kitchen. - Ashland, OR
10 15 reviews

Luxury Condo With King Bedroom, Two Bathrooms, Full Kitchen.

chalet, Ashland
The Sonoma Suite is a one-bedroom apartment situated in Ashland's Historic Downtown District, just a short walk from the Oregon Shakespeare Festival and a range of restaurants and shops.
This 100 square metre apartment, which can accommodate up to four guests, features a modern kitchen, a fireplace, and a spacious bathroom, as well as covered parking and access to a secure foyer and elevator.
Penthouse Suite, Easy Walk To Downtown. - Ashland, OR
10 135 reviews

Penthouse Suite, Easy Walk To Downtown.

bungalow, Ashland
This charming bungalow is situated in a prime location just a 1.6km walk from the heart of Ashland, placing you within easy reach of the Oregon Shakespeare Festival, Lithia Park, and the Lithia Artisans Market. The property consistently receives excellent ratings for its cleanliness, location, and user experience, making it a popular choice for travellers.
The bungalow comfortably accommodates up to eight guests across three bedrooms and two bathrooms. It boasts a fully equipped kitchen, a spacious living area with a gas fireplace, a large deck with a gas grill, and a level 2 car charger for electric vehicles.
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