Best Holiday rentals and Airbnb offers in Ashland, OR
9.5 32 reviews
Ashland, OR
20/08 – 22/08
SG$575/nightTotal: SG$1150 (2 )
Stroll Into Ashland From Abigail's Two Bedroom Private Vacation Cottage.
1 2
cottage , Ashland
Abigail's Self Catering Cottage in Ashland, Oregon, is conveniently located within walking distance of the Ashland Theatres, the Plaza, and Lithia Park. This 65 square metre (700 square foot) self-catering holiday home sleeps four guests in two bedrooms, boasting a fully equipped kitchen, a spa, a garden, parking, and free Wi-Fi.
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.
9.4 16 reviews
Ashland, OR
25/08 – 26/08
SG$314/nightfor 1 night
Chateau Herbe ~ Oberon Suite W/ Kitchen
1 3
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.
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.
10 4 reviews
Ashland, OR
18/09 – 20/09
SG$289/nightTotal: SG$578 (2 )
Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment
1 2
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.
9.4 200 reviews
Ashland, OR
07/10 – 12/10
SG$323/nightTotal: SG$1615 (5 )
The Dogwood Suite At Tudor House Vacation Rentals
1 4
apartment , Ashland
This apartment is situated in the Siskiyou-Hargadine Historic District, just 1.5 kilometres from Southern Oregon University, Ashland Library, and the Oregon Cabaret Theatre, and less than 1.6 kilometres from the Oregon Shakespeare Festival and Thomas Theatre. It has consistently received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom, two-bathroom flat spans 74 square metres and comfortably accommodates up to five guests. Enjoy a fully equipped kitchen, a terrace, a garden, a spa, parking, and free Wi-Fi in public areas, along with a washing machine, a TV and DVD player, and air conditioning.
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.
Ashland, OR
07/10 – 12/10
SG$731/nightTotal: SG$3655 (5 )
Lithia Springs Resort
2 4
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.
9.8 150 reviews
Ashland, OR
26/08 – 27/08
SG$330/nightfor 1 night
Beautiful And Peaceful Cottage Close To Downtown
1 3
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.
10 177 reviews
Ashland, OR
19/07 – 14/08
SG$194/nightTotal: SG$5044 (26 )
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 4 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.
10 4 reviews
Ashland, OR
18/09 – 20/09
SG$937/nightTotal: SG$1874 (2 )
Grandview Of Ashland
1 2
house , Ashland
Grandview of Ashland, a one-bedroom house, is situated near Lithia Park and the Oregon Shakespeare Festival, approximately 2.9 kilometres from each. This self-catering property sleeps up to 11 guests and boasts a fully equipped kitchen, three bathrooms, a Jacuzzi, sauna, private garden, free Wi-Fi, and free private parking; in-unit laundry facilities add further convenience.
Best family friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals
9.9 146 reviews
Ashland, OR
07/10 – 12/10
SG$726/nightTotal: SG$3630 (5 )
The Aloha House - Hot Tub - Pool
1 4
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.
9.7 56 reviews
Ashland, OR
26/08 – 27/08
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 76 reviews
Ashland, OR
20/08 – 22/08
SG$550/nightTotal: SG$1100 (2 )
Pet Friendly W/ Hot Tub By Town!
1 2
apartment , Ashland
This three-bedroom apartment is situated in a residential area, just a short walk from the centre of Ashland, Lithia Park and the Varsity Theatre. The property consistently receives excellent ratings for its location, cleanliness and overall experience. The apartment comfortably accommodates up to six guests and features a well-equipped kitchen, a large garden and a private deck with a barbecue. Guests can enjoy the vintage stereo system, the bar, and the family-friendly games provided.
10 36 reviews
Ashland, OR
27/06 – 04/07
SG$568/nightTotal: SG$3976 (7 )
"Enchantment" Jacksonville, Oregon
4 2
apartment , Medford
This Medford property, a spacious four-bedroom house, is situated 19 kilometres north of Ashland and 11 kilometres south of Jacksonville, offering easy access to the Oregon Shakespeare Festival and Britt Festival. The 251-square-metre dwelling boasts a jacuzzi, terrace, garden, and parking, accommodating eight guests with amenities including a fully equipped kitchen, Wi-Fi, and access to nearby attractions such as the Beekman House and Craterian Ginger Rogers Theatre.
Best Ashland, OR holiday rentals with parking
10 3 reviews
Ashland, OR
04/08 – 06/08
SG$290/nightTotal: SG$580 (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.
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.
Ashland, OR
26/08 – 27/08
SG$823/nightfor 1 night
Whimsy On B- 2br & Studio Near Osf
1 3
studio , Ashland
This studio apartment in Ashland is located an 8-minute walk from Lithia Park and 2.4 kilometres from ScienceWorks Museum, offering convenient access to the Oregon Shakespeare Festival and Oregon Cabaret Theatre. This air-conditioned apartment for 11 guests features a fully equipped kitchen, free Wi-Fi, free private parking, and a balcony with garden views, ideal for self-catering and enjoying the local atmosphere.
Ashland, OR
20/08 – 22/08
SG$929/nightTotal: SG$1858 (2 )
Savage Upon Siskiyou | Prime Osf Location
3 2
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.
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
10 16 reviews
Ashland, OR
20/08 – 22/08
SG$306/nightTotal: SG$612 (2 )
Peaceful, Spacious Home On 8 Acres. Pet-friendly, Close To Town, And A Creek!
2 2
apartment , Ashland
This two-bedroom apartment is situated in a rural setting just 8 kilometres from downtown Ashland, offering a peaceful retreat amidst the natural beauty of the surrounding countryside. The apartment has received excellent user ratings, highlighting its appeal for those seeking a tranquil escape. The apartment, which can accommodate up to six guests, features a spacious living area with high ceilings and ample natural light. The property offers a range of amenities including a private jacuzzi, a terrace, a garden, and a spa, along with parking facilities and access to the internet.
10 14 reviews
Ashland, OR
04/08 – 06/08
SG$725/nightTotal: SG$1450 (2 )
2-story, 3 Bedroom Modern Home With King And Queen Beds, Living Room And Kitchen.
3 2
apartment , Ashland
This modern apartment is situated in Ashland's Historic Downtown District, just a short walk from the ScienceWorks Hands-On Museum and The RRRink. The area is bustling with activity, offering a vibrant mix of shops, restaurants, and cultural attractions. This two-storey property spans 110 square metres and comfortably sleeps up to 8 guests with three bedrooms and two bathrooms. It features a fully equipped kitchen, a smart TV with DVR, a washer/dryer, a jetted tub, a balcony, and a patio.
9.8 30 reviews
Ashland, OR
18/09 – 20/09
SG$1376/nightTotal: SG$2752 (2 )
Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You!
4 2
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.
9.5 187 reviews
Ashland, OR
04/08 – 06/08
SG$888/nightTotal: SG$1776 (2 )
1907 Charmer, Perfect Downtown Location, So Clean!
3 2
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 pet friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best pet friendly rentals
9.9 502 reviews
Ashland, OR
20/08 – 22/08
SG$429/nightTotal: SG$858 (2 )
Victorian Garden Carriage House
1 2
apartment , Ashland
This charming cottage is located just a few hundred metres from Ashland Plaza, offering a peaceful retreat within easy reach of the town's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The cottage is a two-bedroom property with one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a private garden, laundry facilities, a romantic fireplace, and a unique loft accessed by a traditional Japanese staircase cabinet.
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.
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.
Ashland, OR
20/08 – 22/08
SG$953/nightTotal: SG$1906 (2 )
Savage Upon Siskiyou | Prime Osf Location
1 2
apartment , Ashland
This historic Victorian flat is located just 480 metres from the Oregon Shakespeare Festival and the centre of Ashland. This residence accommodates up to eight guests across three bedrooms and a bonus room, featuring a fully equipped kitchen, air conditioning, a garden, and private parking with an EV charger.