Ashland, OR place to staycozycozy

Search accommodations in Ashland, OR

456 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

456 Lodgings in Ashland, OR

Chateau Herb ~ Miranda Carriage House Apt - Ashland, OR
9.8 9 reviews
Ashland, OR
4 2
₹22899/nighttotal: ₹137394 (6 )

Chateau Herb ~ Miranda Carriage House Apt

apartment - Ashland
This two-bedroom, one-bathroom house in Ashland, Oregon is conveniently located approximately 1.6km from Ashland Dog Park and within 4.8km of North Mountain Park, Lithia Park, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre.
The smoke-free property sleeps four guests and offers amenities including a sauna, hot tub, in-house laundry facilities, and is within easy reach of Ashland's major parks and theatres.
Abbott's Cottages - Cardinal - Ashland, OR
9.8 252 reviews
Ashland, OR
2 1
₹11682/nighttotal: ₹128502 (11 )

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.
Carter Lane Wee Casa - Ashland, OR
9.9 14 reviews
Ashland, OR
2 1
₹13144/nighttotal: ₹341744 (26 )

Carter Lane Wee Casa

cabin - Talent
The Wee Casa, a self-catering cottage in Talent, Oregon, is situated on a gated property with other rentals, offering convenient parking and proximity to local amenities.
This one-bedroom, one-bathroom lodge sleeps two guests and features a full kitchen with fridge, freezer and microwave, air conditioning, a garden, and covered outdoor areas; two-car parking is available directly outside.
Chateau Herbe ~ Vienna Room - Ashland, OR
9.8 18 reviews
Ashland, OR
2 1
₹14525/nighttotal: ₹72625 (5 )

Chateau Herbe ~ Vienna Room

castle - Ashland
Château Herbe, near Interstate 5 and Ashland, Oregon, offers a luxurious stay minutes from downtown Ashland and Grizzly Peak Winery.
This French-style château provides a spacious, en-suite room with private patio, sleeping two guests, and access to communal sunroom, library, and coffee bar, plus stunning grounds including vineyards and gardens.
Beautiful Guest Suite With Private Deck Overlooking Forest And Waterfall - Ashland, OR
10 100 reviews
Ashland, OR
2 1
₹17806/nighttotal: ₹89030 (5 )

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.
Gorgeous Log Home In Talent With Sauna - Ashland, OR
Ashland, OR
2 2
₹27329/nighttotal: ₹710554 (26 )

Gorgeous Log Home In Talent With Sauna

cabin - Talent
This two-bedroom, two-bathroom lodge is situated in Talent, offering convenient access to StoneRiver Vineyards and Paschal Winery, with North Mountain Park and Lithia & Driveway Fields also within easy reach.
This pet-friendly retreat accommodates up to four guests and boasts acreage with walking trails, air conditioning, and internet, providing an ideal base for exploring local attractions and enjoying quiet moments.
Savage Upon Siskiyou | Prime Osf Location - Ashland, OR
10 1 review
Ashland, OR
3 3
₹117711/nighttotal: ₹235422 (2 )

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.
Beautiful Ashland Flat - Ashland, OR
9.7 23 reviews
Ashland, OR
2 1
₹11820/nighttotal: ₹59100 (5 )

Beautiful Ashland Flat

apartment - Ashland
This Ashland apartment, ideally located for exploring the city, offers a private upstairs unit with independent access.
The one-bedroom self-contained flat sleeps two guests, boasts a fully equipped kitchen with modern appliances, a private deck, and includes high-speed Wi-Fi and all utilities.
Pioneer Vacation Rentals - Pioneer North - Ashland, OR
9.9 36 reviews
Ashland, OR
4 2
₹27307/nighttotal: ₹163842 (6 )

Pioneer Vacation Rentals - Pioneer North

apartment - Ashland
This historic guesthouse is situated in a charming downtown neighbourhood in Ashland, just a few hundred metres from the theatre and within easy walking distance of restaurants, wineries, and shops. It has consistently received excellent ratings for location, cleanliness, and user experience.
The property is a fully renovated two-bedroom home, originally built in 1904, and comfortably accommodates up to six guests. Modern amenities include a smart TV with DVR, a washer/dryer, a well-equipped kitchen, and a private off-street parking space.
Mountain Ave House By Wanderlodges - Ashland, OR
9.8 10 reviews
Ashland, OR
3 3
₹68172/nighttotal: ₹136344 (2 )

Mountain Ave House By Wanderlodges

apartment - Ashland
This renovated, three-bedroom house in central Ashland, Oregon, is situated 0.8 kilometres from Ashland's plaza, the Oregon Shakespeare Festival, and Lithia Park.
This pet-friendly property offers three king-size bedrooms, two bathrooms, a fully equipped kitchen including dishwasher, a spa, and parking, comfortably accommodating up to six guests, and is close to Grizzly Peak and Weisinger Family wineries.
Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment - Ashland, OR
9.2 7 reviews
Ashland, OR
2 1
₹20872/nighttotal: ₹104360 (5 )

Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment

apartment - Ashland
This one-bedroom Ashland apartment, part of the Chateau Herbe gated community near Interstate 5, offers convenient access to downtown Ashland and is within a few kilometres of Grizzly Peak and Weisinger Family wineries.
The self-contained flat, sleeping two guests, boasts access to shared chateau amenities including a sunroom, library, and coffee bar, plus on-site gardens, orchards, and a vineyard.
Sweet Breeze Bungalow - Ashland, OR
10 141 reviews
Ashland, OR
2 1
₹15995/nighttotal: ₹79975 (5 )

Sweet Breeze Bungalow

apartment - Ashland
This Ashland Railroad District cottage is a five-minute walk from the town centre and within easy walking distance of the Shakespeare Theatres and Lithia Park.
The one-bedroom, one-bathroom self-contained unit sleeps three, features a fully equipped kitchen with dishwasher, air conditioning, private parking, and a garden, offering easy access to hiking trails and wineries.

Best family friendly Ashland, OR lodging

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

The Aloha House - Hot Tub - Pool - Ashland, OR
9.9 157 reviews
Ashland, OR
2 2
₹47662/nighttotal: ₹238310 (5 )

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.
Charming Cottage, Walk To Town. - Ashland, OR
10 793 reviews
Ashland, OR
2 1
₹22699/nighttotal: ₹113495 (5 )

Charming Cottage, Walk To Town.

house - Ashland
This family-friendly cottage is located in the heart of Ashland, just 1 kilometre from both the Ashland Library and the Oregon Shakespeare Festival. The cottage has excellent user, location, and cleanliness ratings.
The cottage is a 56 square metre property that comfortably sleeps four guests in one bedroom. It has a fully equipped kitchen, a terrace, a garden, a spa, and parking.
The Ashland Social | Guest Studio - Ashland, OR
10 27 reviews
Ashland, OR
2 1
₹16478/nighttotal: ₹181258 (11 )

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.
Oberon - Second Spring Property - Ashland, OR
9.9 348 reviews
Ashland, OR
2 1
₹23365/nighttotal: ₹116825 (5 )

Oberon - Second Spring Property

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.

Best Ashland, OR lodging with a pool

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

The Ashland Social | Main House - Ashland, OR
10 35 reviews
Ashland, OR
4 3
₹50894/nighttotal: ₹305364 (6 )

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 19 reviews
Ashland, OR
2 4
₹74809/nighttotal: ₹374045 (5 )

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.
Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You! - Ashland, OR
9.8 37 reviews
Ashland, OR
4 4
₹95719/nighttotal: ₹574314 (6 )

Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You!

farm - Ashland
This farm stay is located just a few kilometres from downtown Ashland, near the Oregon Shakespeare Festival and a range of restaurants, offering a peaceful escape from the city. It has received excellent user ratings, highlighting its high standards.
The farmhouse spans 269 square metres and comfortably accommodates up to 10 guests. It boasts a large in-ground pool, a hot tub, a chef's kitchen, and a variety of recreational activities, including bocce ball, basketball, and a pond with a pergola and swing.
The Carriage House, Winner 2025 Best Of Ashland! - Ashland, OR
9.8 297 reviews
Ashland, OR
3 1
₹24498/nighttotal: ₹48996 (2 )

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 a real gem, and you've got to see the Oregon Shakespeare Festival, it's world-renowned. The historic Lithia Park is a must-visit, it's stunning. If you're into nature, the nearby Rogue River is a must-see, it's beautiful.
  • How can travelers reach Ashland, OR?

    The easiest way to get to Ashland is by flying into the Medford Airport, about 20 minutes away. If you're driving, you can take Interstate 5, and it's about a 3-hour drive from Portland or a 6-hour drive from San Francisco.
  • What outdoor activities can visitors enjoy in and around Ashland, OR?

    Hiking is a big thing here, there are lots of trails around, like the Siskiyou Mountains. You can also go kayaking on the Rogue River, it's a real treat. If you're looking for something more relaxed, there's the Ashland Botanical Gardens, it's a beautiful place to wander around.
  • When is the ideal time to plan a trip to Ashland, OR?

    The best time to visit Ashland is during the summer, from June to August, the weather is perfect. If you're into theatre, the Oregon Shakespeare Festival runs from February to October, so you can catch a show during that time. Spring and autumn are also lovely, but it can be a bit rainy.
  • What are the best walking or cycling routes in Ashland, OR?

    The Lithia Park Loop is a great walking or cycling route, it's about 4 km long and goes around the park. If you're feeling adventurous, you can try the Bear Creek Greenway, it's a 10 km paved trail that goes along Bear Creek.
  • What nearby towns or cities can be explored from Ashland, OR?

    There are loads of places to visit nearby. Medford is just a short drive away, and it's got a cool downtown area. If you want to head to the coast, you can go to Gold Beach, it's about a 2-hour drive. And if you're into wine, you can visit the wineries in the Applegate Valley, it's about 30 minutes away.
  • What amenities can travelers expect from accommodations in Ashland, OR?

    Ashland has a good range of accommodation options, from budget-friendly motels to luxurious hotels. Most places will have Wi-Fi, parking, and breakfast. Some places even have swimming pools or hot tubs.

Popular destinations

Best Ashland, OR accommodations with a garden

Abram's Cottage - Ashland, OR
9.9 127 reviews
Ashland, OR
4 2
₹24783/nighttotal: ₹148698 (6 )

Abram's Cottage

apartment - Ashland
This charming Victorian cottage is situated in a peaceful neighbourhood just a kilometre from the centre of Ashland, close to restaurants, shops, and the theatre district. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The home is ideal for couples, small groups, or families, accommodating up to seven guests. Guests can enjoy a well-equipped kitchen, a private patio with a barbecue, and a washer and dryer, along with additional amenities like a high chair, baby/pet gate, and toiletries.
Blossom View Cottages: Luxurious 3 Bedroom + Den  Near Theaters, Downtown - Ashland, OR
9.6 83 reviews
Ashland, OR
2 3
₹59254/nighttotal: ₹118508 (2 )

Blossom View Cottages: Luxurious 3 Bedroom + Den Near Theaters, Downtown

apartment - Ashland
This charming house is situated in Ashland's Historic Railroad District, just a kilometre from both the Oregon Shakespeare Festival and the Ashland Library. It has received excellent user ratings, making it a popular choice for travellers.
This three-bedroom property spans 130 square metres and can comfortably accommodate up to 10 guests. The house offers a range of amenities, including a fully equipped kitchen, a private patio, a garden, and a spa, ensuring a relaxing and enjoyable stay.
Abbott's Cottages- Raven - Ashland, OR
10 87 reviews
Ashland, OR
4 2
₹28898/nighttotal: ₹173388 (6 )

Abbott's Cottages- Raven

apartment - Ashland
The Raven cottage is situated in a peaceful garden setting overlooking Ashland Creek, just 0.4 kilometres from the centre of Ashland, within easy walking distance of the Oregon Shakespeare Festival.
This two-bedroom cottage offers comfortable accommodation for up to six guests, featuring a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning and a garden.
Pioneer Vacation Rentals - Pioneer South - Ashland, OR
9.8 60 reviews
Ashland, OR
4 3
₹29337/nighttotal: ₹176022 (6 )

Pioneer Vacation Rentals - Pioneer South

apartment - Ashland
This charming bed and breakfast is located just one block from the Ashland Theatre, in a delightful downtown neighbourhood with easy access to dining, wine tasting, and shopping. The property has received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom property comfortably accommodates up to eight guests. It features a well-equipped kitchenette with a fridge, freezer, microwave, and dishwasher, as well as a private garden, parking, and air conditioning.

Best Ashland, OR accommodations with a kitchen

Downtown 3 Bedroom Upstairs Flat With Views "B" - Ashland, OR
9.8 146 reviews
Ashland, OR
2 3
₹36607/nighttotal: ₹183035 (5 )

Downtown 3 Bedroom Upstairs Flat With Views "B"

apartment - Ashland
This house is located in Ashland's Historic Railroad District, just a short walk from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for location, cleanliness and user experience.
The three-bedroom property can comfortably accommodate up to seven guests and features a balcony, a fully equipped kitchen and parking. Amenities include a fridge, freezer, microwave oven, dishwasher, air conditioning, internet access, a garden and a terrace.
Luxury Condo With King Bedroom, Two Bathrooms, Full Kitchen. - Ashland, OR
9.4 11 reviews
Ashland, OR
3 1
₹38109/nighttotal: ₹76218 (2 )

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

chalet - Ashland
This luxury apartment in Ashland's Historic Downtown District is located steps from restaurants and shops, and a short walk from the Oregon Shakespeare Festival venues.
The 100-square-metre (1076 square-foot) condo boasts a king bedroom, two bathrooms, a fully equipped kitchen, and a spacious great room with a fireplace, accommodating up to four guests and offering stunning Ashland Hills views from a private balcony; secure parking and elevator access are also provided.
1907 Charmer, Perfect Downtown Location, So Clean! - Ashland, OR
9.5 197 reviews
Ashland, OR
2 3
₹50106/nighttotal: ₹250530 (5 )

1907 Charmer, Perfect Downtown Location, So Clean!

apartment - Ashland
This house is located in Ashland's Historic Downtown District, just 0.5km from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The 3-bedroom house spans 118 square metres and features a fully equipped kitchen, two bathrooms, a washing machine, and a garden. Guests can enjoy amenities such as air conditioning, parking, and a spa, making it ideal for a comfortable and relaxing stay.
Alice Berry Cottage - Ashland, OR
10 99 reviews
Ashland, OR
4 2
₹27929/nighttotal: ₹167574 (6 )

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.
©2026 cozycozy.com