Best Holiday rentals and Airbnb offers in Ashland, OR
10 177 reviews
Ashland, OR
09/09 – 13/09
SG$231/nighttotal: SG$924 (4 )
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
1 1
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.
10 23 reviews
Ashland, OR
09/09 – 13/09
SG$368/nighttotal: SG$1472 (4 )
Cowslip Historic Main House, Great For Gatherings!
1 1
apartment , Ashland
This four-bedroom apartment is located just 0.2 kilometres from Ashland's bustling town centre, putting you within easy walking distance of shops, restaurants, Lithia Park and the Oregon Shakespeare Festival. It has received excellent ratings for location, cleanliness and user experience. The apartment is spacious and comfortable, sleeping up to eight guests, and features a fully equipped kitchen, air conditioning, parking and internet access. You can also enjoy the beautiful woodwork and leaded glass details of this historic Craftsman property, as well as explore the nearby Lithia Park and its walking trails, gardens and picturesque creek.
9.7 319 reviews
Ashland, OR
15/10 – 19/10
SG$313/nighttotal: SG$1252 (4 )
The Maple Apartment At Tudor House Vacation Rentals
2 1
apartment , Ashland
This apartment is located in the Siskiyou-Hargadine Historic District, just under 2 kilometres from Southern Oregon University and the Oregon Shakespeare Festival. The area is charming and steeped in history, offering a unique and authentic Ashland experience. Guests have consistently rated the apartment as excellent for its location, cleanliness, and overall experience. The apartment offers two bedrooms and two bathrooms, providing ample space for up to six guests within its 84 square metre floor area. It includes a well-equipped kitchen, a terrace, a garden, a spa, and parking, along with internet access, a DVD player, and books, ensuring a comfortable and enjoyable stay.
10 1 review
Ashland, OR
20/08 – 22/08
SG$378/nighttotal: SG$756 (2 )
Casa Amore, Ashland, Cozy Cottage In The Heart Of Historic Ashland
1 2
cottage , Ashland
This holiday let is located in Ashland's Historic Railroad District, offering immediate walking access to the Oregon Shakespeare Festival, Oregon Cabaret Theatre, and numerous restaurants and galleries. This one-bedroom, one-bathroom bungalow accommodates up to four guests and provides essential amenities including internet and air conditioning, with pets welcome.
9.7 56 reviews
Ashland, OR
25/08 – 26/08
SG$537/nightfor 1 night
Barclay Klum House | Soaking Tub & Gourmet Kitchen
1 3
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.
9.8 9 reviews
Ashland, OR
07/10 – 12/10
SG$448/nighttotal: SG$2240 (5 )
Refurbished Barn On Acerage Just Outside Ashland
1 4
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.
10 6 reviews
Ashland, OR
07/10 – 12/10
SG$508/nighttotal: SG$2540 (5 )
European Style Straw Bale Retreat
2 4
apartment , Ashland
This eco-friendly, two-bedroom, two-bathroom apartment in Ashland, Oregon, is situated on 14 wooded acres a short drive from the town centre, offering easy access to Weisinger Family Winery and Grizzly Peak Winery, as well as North Mountain Park and the Cascade-Siskiyou National Monument. The self-catering property features an open-plan layout with earthen floors, vaulted ceilings, a soapstone fireplace, and a hot tub; it sleeps eight guests and is pet-free.
9.7 14 reviews
Ashland, OR
19/07 – 14/08
SG$225/nighttotal: SG$5850 (26 )
Chateau Herbe ~ Rosalind Carriage House 1bdr Apt
1 1
apartment , Ashland
This Ashland carriage house apartment is situated within a gated castle community near Interstate 5, offering easy access to Ashland's city centre and is only a short drive from local attractions. The one-bedroom, one-bathroom apartment sleeps four guests and boasts access to a sunroom, library, coffee bar, and patio within the main chateau, plus on-site amenities including vineyards, gardens, and a pond.
9.5 187 reviews
Ashland, OR
15/10 – 19/10
SG$771/nighttotal: SG$3084 (4 )
1907 Charmer, Perfect Downtown Location, So Clean!
3 1
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.
10 8 reviews
Ashland, OR
18/09 – 20/09
SG$641/nighttotal: SG$1282 (2 )
Delightful 2~bedroom, Pet~friendly Cottage~walking Distance To Everything!
2 2
cottage , Ashland
This Ashland holiday home is located in the Historic Railroad District, a short 4.5km drive from the Oregon Cabaret Theatre and within walking distance of the Ashland Library. The two-bedroom, two-bathroom property sleeps four guests and offers amenities including Wi-Fi, a fully equipped kitchen with dishwasher, in-unit laundry, and air conditioning; nearby attractions include North Mountain Park and the ScienceWorks Hands-On Museum.
9.4 9 reviews
Ashland, OR
26/08 – 27/08
SG$443/nightfor 1 night
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 3
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.
Ashland, OR
19/07 – 14/08
SG$323/nighttotal: SG$8398 (26 )
Swank Suites | King With Lux Tub
1 1
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.
Best family friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals
9.1 2281 reviews
Ashland, OR
07/10 – 12/10
SG$801/nighttotal: SG$4005 (5 )
Lithia Springs Resort
2 4
resort , Ashland
Lithia Springs Resort is located just 2.5 miles from downtown Ashland and the Oregon Shakespeare Festival, offering easy access to the area's cultural attractions. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience. The resort features a range of accommodation options, including suites and bungalows, all decorated in a modern spa-themed style. Guests can enjoy a variety of amenities, including mineral spring water soaking bathtubs, a seasonal outdoor saltwater pool, a hot tub, and a complimentary full breakfast.
10 31 reviews
Ashland, OR
15/10 – 19/10
SG$874/nighttotal: SG$3496 (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.
10 12 reviews
Ashland, OR
15/10 – 19/10
SG$1073/nighttotal: SG$4292 (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.
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.
Best Ashland, OR holiday rentals with parking
9.9 103 reviews
Ashland, OR
09/09 – 13/09
SG$422/nighttotal: SG$1688 (4 )
Lodging And Art Gallery-charming Space Next To Everything, Walk Anywhere!
1 1
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.
9.0 4 reviews
Ashland, OR
04/08 – 06/08
SG$357/nighttotal: SG$714 (2 )
The Matriarch| Suite 3 | Pet Friendly
1 2
apartment , Ashland
This Ashland apartment, a private suite within a historic 1894 Heritage House in the Railroad District, is a 0.4km walk from the Oregon Shakespeare Festival and 0.3km from numerous restaurants. The 30-square-metre self-contained flat features a king-sized bed, a separate living area with streaming services, a kitchenette, and accommodates two guests, offering convenient access to Ashland's shops and attractions.
9.0 4 reviews
Ashland, OR
04/08 – 06/08
SG$745/nighttotal: SG$1490 (2 )
The Matriarch Heritage House- Downtown Ashland
2 2
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.
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.
Frequently asked questions about holiday rentals in Ashland, OR
What are some interesting places to visit in or near Ashland, OR?
Ashland is a great base for exploring the area. You can visit the Oregon Shakespeare Festival, a renowned theatre company, or the Lithia Park, a beautiful park with walking trails, gardens, and a lake. If you're looking for something a bit further afield, you can drive to Crater Lake National Park, a stunning volcanic lake, or the Rogue River, a popular spot for rafting and kayaking.
What are the best Airbnb and vacation rentals in Ashland, OR?
Which walking or cycling routes are the best in Ashland, OR?
The Bear Creek Greenway is a popular choice for both walking and cycling, stretching for 10 km along Bear Creek. For a more challenging ride, try the Siskiyou Mountain Loop, which takes you through the Siskiyou Mountains with stunning views. You can also explore the many trails in Lithia Park, with options for all fitness levels.
What sports or outdoor activites can visitors enjoy in and around Ashland, OR?
Ashland is a great place for outdoor enthusiasts. You can go hiking in the Siskiyou Mountains, fishing in the Rogue River, or kayaking on Lake Siskiyou. In the winter, you can ski or snowboard at Mount Ashland Ski Area, just a short drive from town.
What are the best vacation rentals with a pool in Ashland, OR?
What other towns or cities can be easily accessed from Ashland, OR?
You can easily reach Medford, the largest city in the region, within a 30-minute drive. For a longer day trip, you can visit Crater Lake National Park, about a 2-hour drive from Ashland. If you're looking for a charming small town, Jacksonville is about 15 minutes away and has a historic downtown area.
What are the best rentals for families and kids in Ashland, OR?
What amenities are commonly available in vacation rentals in Ashland, OR?
Vacation rentals in Ashland typically offer a range of amenities, including kitchens, laundry facilities, and Wi-Fi. Many also have outdoor spaces like patios or balconies, and some even have hot tubs or swimming pools. You can often find rentals with specific features like fireplaces or pet-friendly options.
What are the best rentals or Airbnbs with a jacuzzi in Ashland, OR?
What time of year is best to rent a vacation rental Ashland, OR?
The best time to visit Ashland depends on your interests. If you're a theatre enthusiast, the summer months are ideal for attending the Oregon Shakespeare Festival. For mild weather and outdoor activities, spring and autumn are great options. If you enjoy winter sports, you can visit during the winter months.
Destinations nearby
Best Ashland, OR holiday rentals with a balcony
Ashland, OR
03/07 – 06/07
SG$461/nighttotal: SG$1383 (3 )
Lithia Springs Resort
1 2
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.
9.4 11 reviews
Ashland, OR
04/08 – 06/08
SG$443/nighttotal: SG$886 (2 )
Barclay Klum House By Wanderlodges
2 2
apartment , Ashland
This two-bedroom apartment is located in Ashland, Oregon, just a short walk from the Oregon Shakespeare Festival and close to other attractions such as the Schneider Museum of Art and Lithia Park. The 139 square metre property features a fully equipped kitchen, a private balcony with garden views, and parking for guests, making it ideal for families or groups of up to seven people.
10 2 reviews
Ashland, OR
04/08 – 06/08
SG$415/nighttotal: SG$830 (2 )
Moody Ashland Escape: Luxe Suite, Copper Tub
1 2
apartment , Ashland
This first-floor suite, situated in Ashland's Historic Railroad District, is a half-kilometre (0.3 miles) from a grocery store and within a kilometre (0.6-1.2 miles) of restaurants, shops, and cafes. The 28-square-metre apartment, part of The Matriarch's heritage carriage house, offers a Cal King bed, a private patio, a copper soaking tub, and sleeps two guests, providing access to the property grounds.
9.9 334 reviews
Ashland, OR
18/09 – 20/09
SG$524/nighttotal: SG$1048 (2 )
Second Spring Property - 3 Bedroom 2 Bath Luxury Home In The Heart Of Ashland
1 2
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 pet friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best pet friendly rentals
Ashland, OR
07/10 – 12/10
SG$1021/nighttotal: SG$5105 (5 )
Meadowsweet Farm- Sleeps 18, Outdoor Kitchen
7 4
house , Talent
Meadowsweet Farm, a substantial dwelling in Talent, is situated 9.9 kilometres from the Oregon Shakespeare Festival and 10.1 kilometres from Lithia Park, with the ScienceWorks Museum and Schneider Museum of Art also 12.4 kilometres away. This air-conditioned property spans 297 square metres, accommodates up to 18 guests across its three bathrooms, and features an outdoor kitchen, WiFi, and private parking, making it suitable for larger groups seeking a holiday let.
9.5 84 reviews
Ashland, OR
10/07 – 12/07
SG$382/nighttotal: SG$764 (2 )
Studio With King-size Bed
1 2
studio , Ashland
This studio apartment is located in Ashland, just under 1.6km from the Oregon Shakespeare Festival and a little over 1.6km from ScienceWorks Museum, making it an ideal base for exploring the town's cultural attractions. The property has received excellent ratings for its location, cleanliness and overall user experience. The apartment offers one bedroom and one bathroom, comfortably accommodating up to two guests. Amenities include free Wi-Fi, private parking, a king-size bed, a flat-screen TV, and a kitchen equipped with a fridge, freezer, and microwave.
10 26 reviews
Ashland, OR
09/09 – 13/09
SG$281/nighttotal: SG$1124 (4 )
The Ashland Social | Guest Studio
1 1
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.
10 19 reviews
Ashland, OR
25/08 – 26/08
SG$495/nightfor 1 night
Stroll Inn~central Locale!
1 3
apartment , Ashland
This two-bedroom cottage is located in Ashland's historic Siskiyou-Hargadine District, a short walk from Lithia Park and the town's theatres and restaurants. The self-catering property sleeps four, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and a charming front porch; nearby attractions include spas and yoga studios.