Best Holiday rentals and Airbnb offers in Ashland, OR
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.
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.
9.1 38 reviews
Ashland, OR
08/08 – 10/08
SG$914/nighttotal: SG$1828 (2 )
The Mountain House By Wanderlodges
3 4
house , Ashland
The Mountain House by WanderLodges is located in Ashland, just 2.2 kilometres from the ScienceWorks Museum and 2.9 kilometres from the Oregon Shakespeare Festival, making it a convenient base for exploring the town's attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. The three-bedroom house spans 158 square metres and can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, air conditioning, and private parking, ensuring a comfortable and enjoyable stay.
9.9 43 reviews
Ashland, OR
08/08 – 10/08
SG$620/nighttotal: SG$1240 (2 )
Sherwin Cottage
1 4
apartment , Ashland
Sherwin Cottage is situated on Oak Street in Ashland, just a short walk from the town centre and its many shops, restaurants, and theatres. The cottage has received excellent ratings for its location, cleanliness, and overall user experience. The charming cottage sleeps 11 guests comfortably and features two bedrooms and two bathrooms. Amenities include a fully equipped kitchen, air conditioning, parking, and internet access, making it a perfect choice for families or groups of friends.
9.8 6 reviews
Ashland, OR
18/09 – 20/09
SG$479/nighttotal: SG$958 (2 )
Swank Suites | King With Lux Tub
1 2
apartment , Ashland
This Ashland city centre apartment is ideally located less than 0.16km from a grocery store and coffee shop, and within a short walk of restaurants, the Plaza Center, and the Chozu Bath & Tea Gardens. The 37 square metre flat offers a king-size bed, two bathrooms, and a kitchenette with microwave, accommodating two guests and featuring a private outdoor lounge area, high-speed 5G internet, and access to laundry facilities.
Ashland, OR
07/10 – 12/10
SG$300/nighttotal: SG$1500 (5 )
Geodome And Tiny Home Combo
1 4
cabin , Ashland
This glamping lodge is situated in a peaceful district on the outskirts of Ashland, offering a quiet retreat yet providing easy access to the city's acclaimed cultural attractions, approximately 3 kilometres away. This lodge accommodates up to five guests and features a separate geodome for unique sleeping or relaxation, two bathrooms, a full kitchen, air conditioning, a garden, a sauna, and vaulted decks with elevated views, ideal for birdwatching and stargazing.
9.8 61 reviews
Ashland, OR
08/08 – 10/08
SG$943/nighttotal: SG$1886 (2 )
Mountain Ave House By Wanderlodges
1 4
apartment , Ashland
This three-bedroom house, situated in suburban Ashland, Oregon, is conveniently located 0.8 kilometres from Ashland's downtown plaza, offering easy access to restaurants, the Oregon Shakespeare Festival, and Lithia Park. The 3-bedroom property boasts a spacious layout with king-sized beds in each bedroom, accommodating up to six guests, and includes a well-equipped kitchen, two bathrooms, a private garden, parking for two cars, and access to a SMART TV.
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.
9.0 7 reviews
Ashland, OR
08/08 – 10/08
SG$291/nighttotal: SG$582 (2 )
Chateau Herb ~ Juliet Carriage House Studio
1 4
studio , Ashland
This Ashland mountain property is situated approximately 1.6km from Ashland Dog Park and within 4.8km of North Mountain Park and Lithia Park, offering easy access to Ashland's attractions. The one-bedroom, one-bathroom dwelling sleeps four guests and features a private patio, on-site laundry facilities, and is ideal for short or long stays exploring Ashland's natural beauty and cultural offerings such as the Allen Elizabethan Theatre and Angus Bowmer Theatre.
10 2 reviews
Ashland, OR
07/10 – 12/10
SG$419/nighttotal: SG$2095 (5 )
One Bedroom One Bathroom Studio With Full Kitchen And Stunning Patio.
1 4
studio , Ashland
This Ashland cottage, situated in the Historic Railroad District, is within a 1.7km walk of Lithia Park and less than 1km from the Oregon Cabaret Theatre. The one-bedroom, one-bathroom self-catering property sleeps two guests and offers Wi-Fi, air conditioning, and essential toiletries; nearby attractions include the Ashland Creek and US Cellular Community Park.
Ashland, OR
18/09 – 20/09
SG$801/nighttotal: SG$1602 (2 )
Whimsy On B | 2br Steps To Downtown
2 2
apartment , Ashland
This two-bedroom flat is centrally situated in Ashland, a mere 500 metres from the Ashland Food Co-op and within easy walking distance of the town's shops, theatres, and cafes, offering convenient access to the Oregon Shakespeare Festival and Allen Elizabethan Theatre. The accommodation, suitable for four guests, features a king-size bedroom with a television, a second bedroom with a queen-size bed, a living room with a TV, a well-equipped kitchen including a fridge, microwave oven, and dishwasher, air conditioning, Wi-Fi, a private balcony, and off-street parking, all within a peaceful triplex setting.
Ashland, OR
19/07 – 14/08
SG$323/nighttotal: SG$8398 (26 )
Swank Suites | King With Lux Tub
1 1
apartment , Ashland
This Ashland city centre apartment is ideally located within a short walk of the Oregon Shakespeare Festival and Lithia Park, and a block from a grocery store. The 28-square-metre studio flat offers a king-size bed, two bathrooms, a kitchenette with microwave and mini-refrigerator, and access to a private outdoor lounge; it sleeps two guests and boasts high-speed 5G internet.
Best family friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals
9.4 3 reviews
Ashland, OR
07/10 – 12/10
SG$1799/nighttotal: SG$8995 (5 )
Ashland Group Retreat! The Redtail Inn Offers 3 Full Suites Within One Booking, Sleeping Up To 12. Great Location For The Shakespeare Festival. Ample Space For Your Large Family Or Friend Group.
4 4
apartment , Ashland
This six-bedroom apartment, sleeping up to twelve guests, is situated in Ashland's Siskiyou-Hargadine Historic District, within a 1.6km walk of the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library. The 260 square metre property boasts a fully equipped kitchen, Jacuzzi, garden, terrace, parking, and free Wi-Fi; nearby attractions include the Angus Bowmer Theatre and Thomas Theatre, both within 1.6km.
9.1 2280 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.
9.8 43 reviews
Ashland, OR
18/09 – 20/09
SG$489/nighttotal: SG$978 (2 )
Ashland's Mountain View Vacation Rental.
2 2
cottage , Ashland
This charming cottage is situated in Ashland, just 2km from Weisinger Family Winery, Southern Oregon University, and the Schneider Museum of Art, offering a convenient base for exploring the town. It has received excellent reviews from previous guests. The property features two bedrooms, two bathrooms, and can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, parking, and free Wi-Fi.
9.5 187 reviews
Ashland, OR
07/10 – 12/10
SG$996/nighttotal: SG$4980 (5 )
1907 Charmer, Perfect Downtown Location, So Clean!
1 4
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.
Best Ashland, OR holiday rentals with parking
9.6 89 reviews
Ashland, OR
08/08 – 10/08
SG$646/nighttotal: SG$1292 (2 )
Blossom View Cottages - Charming Home Near Osf Plaza And Downtown
2 4
apartment , Ashland
This charming house is located in Ashland's Historic Railroad District, just a kilometre from both the Ashland Library and the Oregon Shakespeare Festival. The house has received excellent user ratings, making it a popular choice for travellers. This two-bedroom property spans 81 square metres and can accommodate up to six guests. The house features a fully equipped kitchen, a private garden, a terrace, a spa, and parking.
10 2 reviews
Ashland, OR
07/10 – 12/10
SG$1262/nighttotal: SG$6310 (5 )
Meadowsweet Farm | Hot Tub, Outdoor Kitchen
7 4
apartment , Talent
This restored farmhouse, situated in Medford, is a mere 700 metres from Paschal Winery and StoneRiver Vineyards, offering a distinctive wine country escape with easy access to downtown Medford's attractions. This family-friendly property accommodates up to 18 guests across 7 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a garden with an outdoor kitchen and fireplace, and parking, making it ideal for large groups seeking a comfortable stay.
10 9 reviews
Ashland, OR
18/09 – 20/09
SG$439/nighttotal: SG$878 (2 )
Peaceful 1-bedroom Bungalow With Ac In Charming Ashland
1 2
apartment , Ashland
This one-bedroom flat is located just 100 metres north of Ashland's downtown plaza, offering convenient walking access to the Oregon Shakespeare Festival, Oregon Cabaret Theatre, shops, restaurants, Lithia Park, and the Japanese Garden. The 46 square metre bungalow accommodates two guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a private patio and garden, and is ideal for those interested in mountain climbing, hiking, and mountain biking.
9.7 72 reviews
Ashland, OR
07/10 – 12/10
SG$565/nighttotal: SG$2825 (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.
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
9.9 332 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.
10 3 reviews
Ashland, OR
18/09 – 20/09
SG$443/nighttotal: SG$886 (2 )
Swank Boutique Suites | Double Shower
1 2
apartment , Ashland
This Ashland Railroad District flat is ideally located, just a short walk from Ashland's downtown attractions, including the Plaza Center and Chozu Bath & Tea Gardens. The 28-square-metre (0.028 hectare) self-catering apartment features a king-size bed, private outdoor lounge access, high-speed internet, and a shared pavilion with laundry facilities, comfortably sleeping two guests.
Ashland, OR
18/09 – 20/09
SG$1173/nighttotal: SG$2346 (2 )
Whimsy On B- 1 Block To Downtown Ashland
2 2
house , Ashland
This holiday cottage in Ashland offers a prime location, a mere 5-minute stroll from the Oregon Shakespeare Festival and 400 metres from the Oregon Cabaret Theatre, placing it conveniently 1 block from downtown Ashland. Guests can enjoy air-conditioned rooms with complimentary private parking and WiFi, featuring a terrace, private bathroom, and flat-screen TV, with no bachelor(ette) or similar parties permitted.
9.8 11 reviews
Ashland, OR
18/09 – 20/09
SG$443/nighttotal: SG$886 (2 )
Hanna's House By Wanderlodges
1 2
house , Ashland
Hanna's House offers a self-catering property in Ashland, Oregon, conveniently located a short walk from the Oregon Shakespeare Festival and Oregon Cabaret Theatre, and within easy reach of the Schneider Museum of Art (1.9km) and Oak Knoll Golf Course (5.6km). This 165 square metre house sleeps seven guests and boasts a well-equipped kitchen, private parking, Wi-Fi, a terrace, garden, and air conditioning; nearby activities include fishing, canoeing, hiking, skiing, golfing, and cycling.
Best pet friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best pet friendly rentals
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.
10 1 review
Ashland, OR
08/08 – 10/08
SG$545/nighttotal: SG$1090 (2 )
Casa Amore, Ashland, Cozy Cottage In The Heart Of Historic Ashland
1 4
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.
9.3 9 reviews
Ashland, OR
08/08 – 10/08
SG$418/nighttotal: SG$836 (2 )
Sunset Cottage At Grizzly Peak Winery
1 4
house , Ashland
Sunset Cottage, a studio apartment at Grizzly Peak Winery near Ashland, Oregon, offers vineyard views and easy access to Ashland's attractions. This self-catering unit sleeps four, features a full kitchen, wood-burning fireplace, smart TV, and complimentary access to winery concerts and food truck meals during the concert season.
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.