Holiday Rentals in Ashland, OR

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Ashland, OR holiday rentals
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Best Holiday rentals and Airbnb offers in Ashland, OR

Best family friendly Ashland, OR holiday rentals

Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals

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. - Ashland, OR
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.
Lithia Springs Resort - Ashland, OR
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.
Ashland's Mountain View Vacation Rental. - Ashland, OR
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.
1907 Charmer, Perfect Downtown Location, So Clean! - Ashland, OR
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

Blossom View Cottages  -  Charming Home Near Osf Plaza And Downtown - Ashland, OR
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.
Meadowsweet Farm | Hot Tub, Outdoor Kitchen - Ashland, OR
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.
Peaceful 1-bedroom Bungalow With Ac In Charming Ashland - Ashland, OR
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.
European Style Straw Bale Retreat - Ashland, OR
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

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Best Ashland, OR holiday rentals with a balcony

Second Spring Property - 3 Bedroom 2 Bath Luxury Home In The Heart Of Ashland - Ashland, OR
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.
Swank Boutique Suites | Double Shower - Ashland, OR
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.
Whimsy On B- 1 Block To Downtown Ashland - Ashland, OR
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.
Hanna's House By Wanderlodges - Ashland, OR
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

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! - Ashland, OR
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.
Casa Amore, Ashland, Cozy Cottage In The Heart Of Historic Ashland - Ashland, OR
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.
Sunset Cottage At Grizzly Peak Winery - Ashland, OR
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.
Meadowsweet Farm- Sleeps 18, Outdoor Kitchen - Ashland, OR
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.
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