Holiday Rentals in Ashland

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Ashland holiday rentals
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Best family friendly Ashland holiday rentals

Among the 203 accommodations in Ashland, 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
9.4 3 reviews
Ashland
10/15 – 10/19
HK$9190/nighttotal: HK$36760 (4 )

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 1
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
9.1 2281 reviews
Ashland
10/07 – 10/12
HK$4884/nighttotal: HK$24420 (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.
"Enchantment"  Medford, Oregon - Ashland
10 36 reviews
Ashland
06/27 – 07/04
HK$3465/nighttotal: HK$24255 (7 )

"Enchantment" Medford, 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.
Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly - Ashland
10 66 reviews
Ashland
08/25 – 08/26
HK$4535/nightfor 1 night

Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

3 3
apartment , Ashland
This Ashland family home, a 148 square metre property, is situated a short 2.4 kilometre walk from Lithia Park and within easy reach of the Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre, plus the Oregon Shakespeare Festival (all within a 2.4 kilometre radius).
The three-bedroom dwelling boasts two bathrooms, sleeps eight guests, offers a fully equipped kitchen (including fridge, microwave, and dishwasher), a jacuzzi, patio, garden, parking, and free Wi-Fi.

Best Ashland holiday rentals with parking

Whimsy On B | 2br Steps To Downtown - Ashland
Ashland
09/09 – 09/13
HK$4188/nighttotal: HK$16752 (4 )

Whimsy On B | 2br Steps To Downtown

2 1
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.
Hanna's House By Wanderlodges - Ashland
9.8 11 reviews
Ashland
08/04 – 08/06
HK$2339/nighttotal: HK$4678 (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.
Whimsy On B | 2br + Studio Near Osf - Ashland
Ashland
08/26 – 08/27
HK$4949/nightfor 1 night

Whimsy On B | 2br + Studio Near Osf

3 3
studio , Ashland
This residence, a detached studio flat, is centrally located in Ashland's city centre, a 5-minute walk from the Oregon Shakespeare Festival and two blocks from the main shopping and dining area.
This property offers a king-size bed, a kitchenette, and a bathroom, accommodating up to six guests across its main two-bedroom dwelling and separate studio, with a private courtyard and porch available for use.
Chateau Herb ~ Miranda Carriage House Apt - Ashland
9.8 8 reviews
Ashland
09/18 – 09/20
HK$1947/nighttotal: HK$3894 (2 )

Chateau Herb ~ Miranda Carriage House Apt

2 2
apartment , Ashland
This two-bedroom, one-bathroom house in Ashland, Oregon is conveniently located approximately 1.6km from Ashland Dog Park and within 4.8km of North Mountain Park, Lithia Park, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre.
The smoke-free property sleeps four guests and offers amenities including a sauna, hot tub, in-house laundry facilities, and is within easy reach of Ashland's major parks and theatres.

Frequently asked questions about holiday rentals in Ashland

  • What are some interesting places to visit in or near Ashland, OR?

    Ashland is known for its beautiful natural surroundings and cultural attractions. You can visit the Lithia Park, a stunning 190-acre park with a botanical garden, a lake, and walking trails. The Oregon Shakespeare Festival is a must-see for theatre enthusiasts, and the Ashland Art Center showcases local artists' work. Just outside of town, you'll find the Rogue River, perfect for kayaking or rafting, and the Siskiyou Mountains for hiking and exploring.
  • What are the best Airbnb and vacation rentals in Ashland?

  • Which walking or cycling routes are the best in Ashland, OR?

    The Bear Creek Greenway is a popular choice for both walkers and cyclists, offering a scenic 10km paved path along Bear Creek. For a more challenging ride, try the Siskiyou Mountain Loop, a 60km route with stunning views of the Cascade Range. The Lithia Park loop is also a great option for a leisurely stroll, taking you past the park's main attractions.
  • What are the most popular Airbnbs in Ashland?

  • What sports or outdoor activites can visitors enjoy in and around Ashland, OR?

    Ashland is an outdoor enthusiast's paradise! You can go hiking, mountain biking, and rock climbing in the surrounding Siskiyou Mountains. The Rogue River is great for kayaking, rafting, and fishing. In the winter, you can go skiing at Mount Ashland Ski Area, just a short drive away.
  • What are the best vacation rentals with a pool in Ashland?

  • What other towns or cities can be easily accessed from Ashland, OR?

    Ashland is conveniently located near other interesting towns and cities. You can easily drive to Medford, about 20 minutes away, which offers a wider range of shopping and dining options. The city of Grants Pass is about 45 minutes away and is known for its historic downtown and outdoor recreation opportunities. For a longer trip, you can visit Crater Lake National Park, about 2 hours away, and see the stunning beauty of the deepest lake in the United States.
  • What are the best rentals for families and kids in Ashland?

  • What amenities are commonly available in vacation rentals in Ashland, OR?

    Vacation rentals in Ashland typically offer a range of amenities to make your stay comfortable. Most rentals include a fully equipped kitchen, laundry facilities, and Wi-Fi. Many also have outdoor spaces like patios or balconies, and some may even have hot tubs or swimming pools.
  • What are the best rentals or Airbnbs with a jacuzzi in Ashland?

  • 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 enjoy warm weather and outdoor activities, summer is the best time to visit. For a more peaceful experience, spring or autumn are good options. If you're interested in seeing the Oregon Shakespeare Festival, the season runs from February to October.

Destinations nearby

Best Ashland holiday rentals with a balcony

Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You! - Ashland
9.8 30 reviews
Ashland
09/18 – 09/20
HK$8391/nighttotal: HK$16782 (2 )

Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You!

4 2
manor house , 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.
Savage Upon Siskiyou | Prime Osf Location - Ashland
Ashland
08/04 – 08/06
HK$3598/nighttotal: HK$7196 (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.
Chateau Herbe ~ Oberon Suite W/ Kitchen - Ashland
9.4 16 reviews
Ashland
08/20 – 08/22
HK$1601/nighttotal: HK$3202 (2 )

Chateau Herbe ~ Oberon Suite W/ Kitchen

1 2
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.
Pioneer Vacation Rentals - Pioneer Craftsman House - Ashland
8.5 2 reviews
Ashland
08/04 – 08/06
HK$4540/nighttotal: HK$9080 (2 )

Pioneer Vacation Rentals - Pioneer Craftsman House

3 2
house , Ashland
This Craftsman-style holiday home is situated in Ashland, Oregon, a short walk (less than 1.6km) from Lithia Park and within a couple of miles (approximately 3.2km) of Southern Oregon University, the ScienceWorks Museum, and the Schneider Museum of Art.
The 167 square metre property boasts three bedrooms, two bathrooms, and sleeps eight, featuring a fully equipped kitchen, private parking, a terrace, and garden; guests can enjoy nearby attractions such as the Oregon Shakespeare Festival and Oregon Cabaret Theatre.

Best pet friendly Ashland holiday rentals

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

Cowslip's Quiet, Central, Cuckoo-bud Suite - Ashland
9.8 51 reviews
Ashland
09/09 – 09/13
HK$1732/nighttotal: HK$6928 (4 )

Cowslip's Quiet, Central, Cuckoo-bud Suite

1 1
apartment , Ashland
This charming apartment is situated just 0.8 kilometres from the centre of Ashland, offering a peaceful retreat in a quiet residential neighbourhood. Guests consistently rate the apartment as excellent for its cleanliness, location and overall experience.
The apartment features a private kitchenette, perfect for preparing simple meals, and can comfortably accommodate up to three guests. Enjoy the serene atmosphere of the shared garden, complete with a koi pond and trickling waterfall, and benefit from the convenience of off-street parking.
Bluemoon Vacation Rentals - Anne Hathaway House - Ashland
Ashland
10/15 – 10/19
HK$4382/nighttotal: HK$17528 (4 )

Bluemoon Vacation Rentals - Anne Hathaway House

8 1
house , Ashland
The Anne Hathaway House is situated in Ashland, a 1.7 kilometre walk from Southern Oregon University and 1.8 kilometres from the ScienceWorks Museum.
This eight-bedroom home, spanning 334 square metres, can accommodate up to 31 guests and features a fully equipped kitchen, a garden, private parking, and free Wi-Fi.
Relax In The Luxurious 1-bedroom Louisa Suite At Redtail Inn. Enjoy A Double Rain Shower, Plush Linens, And A Shared Hot Tub. Located Near Downtown Ashland, With Off-street Parking And High-speed Wifi. - Ashland
10 12 reviews
Ashland
08/20 – 08/22
HK$2500/nighttotal: HK$5000 (2 )

Relax In The Luxurious 1-bedroom Louisa Suite At Redtail Inn. Enjoy A Double Rain Shower, Plush Linens, And A Shared Hot Tub. Located Near Downtown Ashland, With Off-street Parking And High-speed Wifi.

1 2
apartment , Ashland
This Ashland apartment, situated in the Siskiyou-Hargadine Historic District, is less than 0.6 km from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library.
The 37-square-metre flat features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private patio, hot tub access, and free Wi-Fi.
Centrally Located Downtown Historic Home W/parking - Ashland
9.7 43 reviews
Ashland
08/25 – 08/26
HK$4036/nightfor 1 night

Centrally Located Downtown Historic Home W/parking

1 3
apartment , Ashland
This Ashland, Oregon house, built in 1887, is centrally located, within walking distance of Ashland's downtown area and a short distance (less than 1.6km) from Lithia Park.
Sleeping six guests across three bedrooms and one bathroom, this property offers a well-equipped kitchen, air conditioning, parking, internet access, and pet-friendly facilities.
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