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

The Aloha House - Hot Tub - Pool - Ashland, OR
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.
Barclay Klum House | Soaking Tub & Gourmet Kitchen - Ashland, OR
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.
Pet Friendly W/ Hot Tub By Town! - Ashland, OR
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.
"Enchantment"  Jacksonville, Oregon - Ashland, OR
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

Swank Boutique Suites | Double Shower - Ashland, OR
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.
Hot Tub | Sauna |Firepit |Sleeps 6! - Ashland, OR
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.
Whimsy On B- 2br & Studio Near Osf - Ashland, OR
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.
Savage Upon Siskiyou | Prime Osf Location - Ashland, OR
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

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Best Ashland, OR holiday rentals with a balcony

Peaceful, Spacious Home On 8 Acres. Pet-friendly, Close To Town, And A Creek! - Ashland, OR
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.
2-story, 3 Bedroom Modern Home With King And Queen Beds, Living Room And Kitchen. - Ashland, OR
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.
Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You! - Ashland, OR
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.
1907 Charmer, Perfect Downtown Location, So Clean! - Ashland, OR
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

Victorian Garden Carriage House - Ashland, OR
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.
Lithia Springs Resort - Ashland, OR
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.
Studio With King-size Bed - Ashland, OR
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.
Savage Upon Siskiyou | Prime Osf Location - Ashland, OR
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.
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