This Ashland wine country cottage, situated on the Weisinger Family Winery property, is close to Ashland's city centre and a short drive (distances unspecified) from Lithia Park and the Oregon Shakespeare Festival. The self-catering property, sleeping two guests in one bedroom and one bathroom, offers a private hot tub, BBQ deck, complimentary wine tasting, and modern amenities including WiFi, Direct TV, Roku, Netflix, and Pandora, alongside a fully equipped kitchen.
9.7 896 reviews
Ashland, OR
19/07 – 14/08
SG$82/nighttotal: SG$2132 (26 )
The Deep Blue Metallic Dream Machine
1 1
campervan , Ashland
This minimalist tiny house camper, near downtown Ashland, Oregon, offers a unique stay approximately 0.8 kilometres from Interstate 5 and close to Bear Creek, providing scenic views of Grizzly Peak. The 6'x12' (1.8m x 3.7m) self-catering unit sleeps one, including a kitchenette with fridge, freezer and microwave, air conditioning, and access to a shared outdoor bathhouse with a hot shower; pets are welcome.
9.4 8 reviews
Ashland, OR
08/08 – 10/08
SG$516/nighttotal: SG$1032 (2 )
Charming 1 Br Orliena Suite In Historic Downtown Ashland, Or. Walk To The Oregon Shakespeare Festival, Shops, And Dining. Features A Kitchenette, Plush Queen Bed, And Shared Hot Tub Access. Dog Friendly!
1 4
apartment , Ashland
This Ashland apartment, situated in the Siskiyou-Hargadine Historic District, is less than 0.8 km from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library. The 56 square metre property features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, Jacuzzi, patio, free Wi-Fi, and parking.
9.8 150 reviews
Ashland, OR
15/10 – 19/10
SG$324/nighttotal: SG$1296 (4 )
Beautiful And Peaceful Cottage Close To Downtown
1 1
apartment , Ashland
This charming house is located in the Siskiyou-Hargadine Historic District, just 1.5 kilometres from Southern Oregon University and the Oregon Shakespeare Festival. It has consistently received excellent ratings for location, cleanliness, and overall experience. This one-bedroom property offers 93 square metres of space and can comfortably accommodate five guests. The house features a fully equipped kitchen, a fireplace, a washing machine, a terrace, a garden, and parking, making it ideal for a comfortable and enjoyable stay in Ashland.
9.6 116 reviews
Ashland, OR
08/08 – 10/08
SG$285/nighttotal: SG$570 (2 )
Starlight Cottage At Chozu Gardens
1 4
bungalow , Ashland
This Ashland cottage is located in the historic railroad district, a 0.8 km walk from the downtown area and adjacent to Chozu Gardens, offering a 20% discount (excluding Mondays and Tuesdays). The self-catering studio, sleeping up to four guests, features a full kitchenette with refrigerator, microwave, toaster oven and hot plate, a comfortable orthopedic bed, and a semi-private bedroom with a skylight.
9.7 72 reviews
Ashland, OR
07/10 – 12/10
SG$538/nighttotal: SG$2690 (5 )
European Style Straw Bale Retreat
2 4
house , Ashland
This European-style straw bale home is located on 14 wooded acres in Ashland, just a few kilometres from the town centre and its restaurants, theatres, and shops. The apartment has consistently received excellent ratings for user experience, location, and cleanliness. The two-bedroom home has a spacious open-plan living area with vaulted ceilings and earthen floors, covering 153 square metres. This eco-friendly dwelling offers a unique and sustainable experience with amenities including a fireplace, a terrace, a garden, a spa, parking, and internet access.
9.6 30 reviews
Ashland, OR
15/10 – 19/10
SG$195/nighttotal: SG$780 (4 )
Florence Room At Chateau Herbe
1 1
castle , Ashland
Château Herbe, near I-5 and Ashland, Oregon's city centre, offers a unique stay minutes from Grizzly Peak and Weisinger Family wineries. This one-bedroom castle apartment, sleeping two, features a private en-suite bathroom, queen-sized bed, and access to shared chateau facilities including a sunroom, library, coffee bar, and patio, alongside on-site gardens, orchards, and a pond.
9.3 35 reviews
Ashland, OR
27/08 – 02/09
SG$335/nighttotal: SG$2010 (6 )
Bluemoon Vacation Rentals - Bluemoon Cottage
1 4
apartment , Ashland
Bluemoon Cottage, a one-bedroom apartment in Ashland, offers a peaceful retreat near local wineries, though precise distances require further clarification. This self-catering cottage sleeps up to four guests, featuring a fully equipped kitchen, a private patio, and a futon in the living room; further details regarding the property's size and proximity to Ashland's attractions are needed.
10 5 reviews
Ashland, OR
18/09 – 20/09
SG$1176/nighttotal: SG$2352 (2 )
Hot Tub | Sauna |Firepit |Sleeps 6!
2 2
apartment , Ashland
This luxurious Ashland apartment, close to Lithia Park and the Oregon Shakespeare Festival, offers easy access to wineries such as Grizzly Peak and Weisinger Family, and is within a few kilometres of hiking and mountain biking trails. The two-bedroom property, sleeping up to six guests with a pull-out sofa bed and boasting three bathrooms, features a gourmet kitchen with wine fridge, hot tub, sauna, outdoor fire pit, and a terrace with sweeping valley views; a 20% discount on Oregon Shakespeare Festival B and C section tickets is also included.
9.7 21 reviews
Ashland, OR
08/08 – 10/08
SG$294/nighttotal: SG$588 (2 )
Chateau Herbe ~ Juliet Carriage House Studio
1 4
apartment , Ashland
This one-bedroom Ashland carriage house apartment is situated within a gated community minutes from Interstate 5 and Ashland's city centre, offering easy access to both. The self-catering apartment, sleeping four, boasts a jacuzzi, sauna, and access to shared facilities including a sunroom, library, and coffee bar, plus on-site vineyards, gardens, and orchards.
9.4 204 reviews
Ashland, OR
08/08 – 10/08
SG$237/nighttotal: SG$474 (2 )
Peace And Joy Mini Farm
2 4
gîte , Ashland
This Ashland countryside self-catering property is located 5 minutes (approximately 8km) from Ashland's town centre, providing easy access to the Oregon Shakespeare Festival and within a short drive of Mount Ashland Ski Area. This pet-friendly holiday home offers two bedrooms, one bathroom, sleeping up to four guests, and features a mini-farm, BBQ area, on-site beauty salon, free parking, and excellent guest reviews.
9.0 2 reviews
Ashland, OR
07/10 – 12/10
SG$532/nighttotal: SG$2660 (5 )
5br Two Homes On Creek
5 4
apartment , Ashland
This tranquil five-bedroom, two-bathroom rental property offers direct access to Neil Creek and is situated on a private one-acre lot, conveniently located less than 1 kilometre from the M5 motorway and close to downtown Ashland. This accommodation provides a giant wood barrel hot tub, two fully equipped kitchens, and an outdoor yoga space, perfect for up to 11 guests seeking relaxation and proximity to Ashland's attractions.
Best family friendly Ashland, OR lodging
Among the 301 accommodations in Ashland, OR, here are the 4 best for families
9.7 56 reviews
Ashland, OR
27/08 – 02/09
SG$491/nighttotal: SG$2946 (6 )
Barclay Klum House | Soaking Tub & Gourmet Kitchen
1 4
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.
10 8 reviews
Ashland, OR
15/10 – 19/10
SG$497/nighttotal: SG$1988 (4 )
Barclay Klum House By Wanderlodges
1 1
house , Ashland
This comfortable house is located just 1.5 kilometres from Ashland Library and the Oregon Shakespeare Festival, making it ideal for exploring the town's cultural attractions. The surrounding area is peaceful and quiet, perfect for a relaxing getaway. The property features a fully equipped kitchen, a spacious garden and a terrace, allowing guests to enjoy both indoor and outdoor living. The house also offers a range of amenities, including free Wi-Fi, parking and a Jacuzzi for ultimate relaxation.
9.9 102 reviews
Ashland, OR
15/10 – 19/10
SG$298/nighttotal: SG$1192 (4 )
20% Off Osf Tix In B&c Sections For Guests! 5-min Walk To Downtwn, Private Yard
1 1
cottage , Ashland
This charming cottage is located in Ashland's Historic Railroad District, just a short walk (less than 1 km) from the Ashland Library, Oregon Cabaret Theatre, and Allen Elizabethan Theatre. This well-rated property has received excellent reviews for its cleanliness, location, and overall experience. The 37 square metre cottage can accommodate up to 3 guests and features a comfortable bedroom, a fully equipped kitchen, and a private garden with a patio. Amenities include air conditioning, free Wi-Fi, and a smoke-free environment, allowing you to relax and enjoy your stay.
9.6 19 reviews
Ashland, OR
15/10 – 19/10
SG$924/nighttotal: SG$3696 (4 )
House + 2 Studios- 3 Blocks From The Plaza!
4 1
studio , Ashland
This five-bedroom Ashland house, perfect for families, is situated within a 1.6km walk of Lithia Park and the Allen Elizabethan Theatre, offering easy access to the Oregon Shakespeare Festival. The 121-square-metre property boasts four bathrooms, sleeps sixteen guests, includes a fully equipped kitchen, free Wi-Fi, and a terrace; a sofa bed provides extra sleeping arrangements.
Best Ashland, OR lodgings with a pool
Among the 301 accommodations in Ashland, OR, here are the 4 best ones with a pool
10 31 reviews
Ashland, OR
15/10 – 19/10
SG$898/nighttotal: SG$3592 (4 )
The Ashland Social | Main House
3 1
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.
9.9 146 reviews
Ashland, OR
15/10 – 19/10
SG$690/nighttotal: SG$2760 (4 )
The Aloha House - Hot Tub - Pool
1 1
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.
10 12 reviews
Ashland, OR
15/10 – 19/10
SG$1118/nighttotal: SG$4472 (4 )
The Ashland Social | Entire Estate
4 1
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.
9.6 4 reviews
Ashland, OR
07/10 – 12/10
SG$1665/nighttotal: SG$8325 (5 )
Luxury Ashland Mountain Escape: Pool, Hot Tub
4 4
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.
Frequently asked questions about accommodations in Ashland, OR
What are the must-see sites in or near Ashland, OR?
Ashland is full of things to see! You definitely want to check out the Oregon Shakespeare Festival, a world-renowned theatre company. The Lithia Park is a beautiful spot right in the heart of town, with a stunning waterfall. And for stunning scenery, drive up to the top of Mount Ashland for panoramic views of the Rogue Valley.
The easiest way to get to Ashland is by flying into the Medford Rogue Valley International Airport, which is about 20 minutes away. You can also drive, as Ashland is located off Interstate 5. If you're feeling adventurous, you can take Amtrak's Coast Starlight train, which stops in nearby Klamath Falls.
What 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! You can hike to the top of Mount Ashland, go fishing in the Rogue River, or explore the Siskiyou Mountains on a scenic drive. There are also plenty of trails for mountain biking and horseback riding.
What are the best accommodations with a jacuzzi in Ashland, OR?
When is the ideal time to plan a trip to Ashland, OR?
The best time to visit Ashland is during the summer, when the weather is warm and sunny. The Oregon Shakespeare Festival is in full swing during this time, so you can enjoy a variety of performances. If you're looking for a quieter experience, spring or autumn are also good times to visit.
What are the best accommodations for families and kids in Ashland, OR?
What are the best walking or cycling routes in Ashland, OR?
The Lithia Park Loop Trail is a great option for a leisurely walk or bike ride. It's a 2.5 km paved loop that winds through the park, offering stunning views of the Rogue River and the surrounding mountains. For a more challenging ride, try the Bear Creek Greenway, which stretches for 16 km along the Bear Creek.
What are the best pet friendly accommodations in Ashland, OR?
What nearby towns or cities can be explored from Ashland, OR?
You can easily take a day trip from Ashland to nearby Medford, which is about 20 minutes away. Medford has a charming downtown area with shops and restaurants, and it's also home to the Rogue Valley Mall. Another option is to drive to Jacksonville, a historic gold rush town that's about 30 minutes away.
What 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. Many accommodations offer amenities like swimming pools, hot tubs, and fitness centres. You can also find places with kitchens, laundry facilities, and free Wi-Fi.
Destinations nearby
Best Ashland, OR accommodations with a garden
10 2 reviews
Ashland, OR
07/10 – 12/10
SG$2695/nighttotal: SG$13475 (5 )
Illuminate Retreat And Workshop
5 4
house , Talent
This five-bedroom, four-bathroom house in Talent, Oregon, sits on a 3-acre hilltop plot approximately 11 kilometres from Ashland's town centre, offering stunning mountain views. Sleeping up to 14 guests, this property boasts a chef's kitchen with a gas island, a home theatre, swimming pool, hot tub, cold plunge pool, a large workshop suitable for yoga or group activities, and multiple outdoor decks.
9.2 75 reviews
Ashland, OR
07/10 – 12/10
SG$249/nighttotal: SG$1245 (5 )
Ashland Creekside Cottage
1 4
apartment , Ashland
This remodelled two-bedroom house is situated on a unique 3/4 acre property along Neil Creek, offering direct water access and a tranquil creekside setting, conveniently located less than 1 kilometre from I-5 exit 14 and centrally positioned within Ashland for easy access to town amenities and a short drive to Mt. Ashland. The property accommodates up to six guests and features a garden, air conditioning, and a kitchen equipped with a fridge, freezer, and microwave, alongside a shared yoga pergola for relaxation, with the surrounding area ideal for bird watching and nature enjoyment, and a golf course directly across the street.
9.8 8 reviews
Ashland, OR
27/08 – 02/09
SG$309/nighttotal: SG$1854 (6 )
Chateau Herb ~ Miranda Carriage House Apt
2 4
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.
9.9 34 reviews
Ashland, OR
08/08 – 10/08
SG$1140/nighttotal: SG$2280 (2 )
Grandview Of Ashland | Hot Tub | Sauna | Firepit
1 4
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.
Best Ashland, OR accommodations with a kitchen
9.4 16 reviews
Ashland, OR
07/10 – 12/10
SG$252/nighttotal: SG$1260 (5 )
Chateau Herbe ~ Oberon Suite W/ Kitchen
1 4
apartment , Ashland
This Ashland apartment, a mile (1.6km) from Ashland Dog Park and within three miles (4.8km) of Lithia Park, North Mountain Park, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre, offers stunning mountainside views. The one-bedroom, one-bathroom flat sleeps four, boasting a fully equipped kitchen, private balcony, shared garden, Smart TV, and parking; nearby activities include exploring Ashland's renowned parks and theatres.
Ashland, OR
18/09 – 20/09
SG$479/nighttotal: SG$958 (2 )
Swank Suites | King With Lux Tub
1 2
apartment , Ashland
This Ashland apartment, a stone's throw from the Plaza Centre and a short walk (less than 0.8 km) from a grocery store, offers prime downtown accommodation near Ashland's key attractions. The 28-square-metre flat features two bathrooms, sleeps two guests, includes a kitchenette with microwave, and boasts a private terrace, high-speed 5G internet, and a king-size bed.
9.7 52 reviews
Ashland, OR
07/10 – 12/10
SG$260/nighttotal: SG$1300 (5 )
Ashland Creekside Home
1 4
apartment , Ashland
This remodelled three-bedroom flat offers a creekside location on Neil Creek, providing 0.96 hectares of wooded seclusion yet remaining conveniently located less than 1.6 kilometres from the interstate and close to town. This property accommodates up to seven guests and features air conditioning, a garden, an outdoor yoga pergola, and is adjacent to the Ashland Golf Course, with a kitchen equipped with a fridge, freezer, and microwave oven.
10 2 reviews
Ashland, OR
19/07 – 14/08
SG$174/nighttotal: SG$4524 (26 )
Country Studio, Peaceful Retreat
1 1
house , Ashland
This detached studio accommodation is situated in a rural setting on 2.4 hectares, a short drive from Ashland's amenities and the Oregon Shakespeare Festival. The property sleeps four guests, offering a fully equipped kitchen, a queen-sized bed, a sofa, a futon, air conditioning, internet access, a swimming pool, and a private bathroom, with outdoor features including a porch and fire pit.