Holiday Rentals in Ashland, OR

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Ashland, OR holiday rentals
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203 Holiday rentals and Airbnb 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 Ashland Social | Entire Estate - Ashland, OR
10 12 reviews
Ashland, OR
15/10 – 19/10
722 €/nighttotal: 2888 € (4 )

The Ashland Social | Entire Estate

4 1
apartment , Ashland
This five-bedroom Ashland house, sleeping up to twelve guests, is conveniently located less than 1.2km from Southern Oregon University and the Schneider Museum of Art, and under 2km from North Mountain Park and the Oregon Cabaret Theatre.
The 282-square-metre property boasts five bathrooms, a private swimming pool, Jacuzzi, sauna, terrace, garden, and fully equipped kitchen; free Wi-Fi and parking are also included.
Barclay Klum House | Walk To Downtown | Soaking Tub & Gourmet Kitchen - Ashland, OR
10 5 reviews
Ashland, OR
09/09 – 13/09
498 €/nighttotal: 1992 € (4 )

Barclay Klum House | Walk To Downtown | Soaking Tub & Gourmet Kitchen

2 1
apartment , Ashland
This Queen Anne-style holiday home in Ashland, Oregon, is situated less than 1.6km from the downtown area, offering easy access to shops, theatres, and restaurants.
The 500 square metre property boasts two bedrooms, one bathroom with a luxurious soaking tub and walk-in shower, a full kitchen including a gas stove and grill, three off-street parking spaces, a fully fenced garden, and can comfortably accommodate four guests.
Beautiful And Peaceful Cottage Close To Downtown - Ashland, OR
9.8 151 reviews
Ashland, OR
15/10 – 19/10
213 €/nighttotal: 852 € (4 )

Beautiful And Peaceful Cottage Close To Downtown

1 1
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.
Barclay Klum House By Wanderlodges - Ashland, OR
10 8 reviews
Ashland, OR
15/10 – 19/10
334 €/nighttotal: 1336 € (4 )

Barclay Klum House By Wanderlodges

1 1
house , Ashland
This comfortable house is located just 1.5 kilometres from Ashland Library and the Oregon Shakespeare Festival, making it ideal for exploring the town's cultural attractions. The surrounding area is peaceful and quiet, perfect for a relaxing getaway.
The property features a fully equipped kitchen, a spacious garden and a terrace, allowing guests to enjoy both indoor and outdoor living. The house also offers a range of amenities, including free Wi-Fi, parking and a Jacuzzi for ultimate relaxation.

Best Ashland, OR holiday rentals with parking

Stroll Into Ashland From Abigail's Two Bedroom Private Vacation Cottage. - Ashland, OR
9.5 32 reviews
Ashland, OR
20/08 – 22/08
387 €/nighttotal: 774 € (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.
Swank Suites | Step Free  King - Ashland, OR
8.8 3 reviews
Ashland, OR
20/08 – 22/08
238 €/nighttotal: 476 € (2 )

Swank Suites | Step Free King

1 2
apartment , Ashland
This first-floor apartment in Ashland's historic Railroad District is situated one block from a grocery store and coffee shop, two blocks from an escape room, and within easy walking distance of downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens.
The 37-square-metre (approximately 398 square feet) flat offers a king-size bed, a kitchenette, a private outdoor lounge, shared laundry facilities, high-speed 5G internet, a 65-inch smart TV with Netflix, and accommodates two guests; parking is also available.
Swank Suites + Private Porch Patio - Ashland, OR
9.4 3 reviews
Ashland, OR
04/08 – 06/08
208 €/nighttotal: 416 € (2 )

Swank Suites + Private Porch Patio

1 2
apartment , Ashland
This Premier Suite, situated in Ashland's Historic Railroad District, is a one-minute walk from a grocery store and coffee shop, two minutes from an escape room, and within easy walking distance of downtown restaurants, the Plaza Centre, and Chozu Bath & Tea Gardens.
This 37-square-metre (approximately 398 square feet) first-floor apartment features a king-size bed, a jetted tub, a kitchenette with microwave and mini-refrigerator, private outdoor lounge access, high-speed 5G internet, and accommodates two guests.
Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.6 4 reviews
Ashland, OR
07/10 – 12/10
1120 €/nighttotal: 5600 € (5 )

Luxury Ashland Mountain Escape: Pool, Hot Tub

4 4
house , Ashland
This waterfront villa near Ashland, Oregon, is located 1.4 kilometres from Weisinger Family Winery and 4.8 kilometres from Southern Oregon University.
The 353-square-metre property boasts four bedrooms, four bathrooms, and sleeps twelve guests, offering a private pool, hot tub, barbecue grills, and a fully equipped kitchen including a dishwasher; laundry facilities are also provided.

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 place to visit! You can't miss the Oregon Shakespeare Festival, which runs throughout the summer. If you're a nature lover, head to the Lithia Park, which has lots of hiking trails and beautiful scenery. For a more active day, try the Ashland Hills Golf Course or take a scenic drive to the Rogue River.
  • What are the best Airbnb and holiday rentals in Ashland, OR?

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

    For a relaxing walk, try the Lithia Park Loop Trail. It's a 2.5km paved path that goes around the park. If you're looking for a more challenging bike ride, head to the Bear Creek Greenway. It's a 16km paved trail that goes through the forest and along the creek.
  • What are the most popular Airbnbs in Ashland, OR?

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

    Ashland is a great place to enjoy the outdoors. You can hike, bike, or even go rock climbing in the surrounding mountains. In the summer, there's great fishing in the Rogue River. If you're feeling adventurous, try whitewater rafting or kayaking.
  • What are the best holiday rentals with a pool in Ashland, OR?

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

    Ashland is a great base for exploring Southern Oregon. You can easily drive to Medford, which is about 20 minutes away. It's a larger city with more shops and restaurants. Further afield, you can visit the Crater Lake National Park, which is about a 2-hour drive away.
  • 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 have all the amenities you need for a comfortable stay. You can expect to find a fully equipped kitchen, a comfortable living space, and bedrooms with comfortable beds. Many rentals also have laundry facilities, a patio or balcony, and Wi-Fi.
  • 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 what you're looking for. The summer is the busiest time, with the Oregon Shakespeare Festival in full swing. If you prefer cooler weather and fewer crowds, consider visiting in the spring or autumn.
  • What are the local dishes in Ashland, OR region?

    The local cuisine in the Ashland area features fresh, seasonal ingredients. Try a local favourite, the Rogue River trout, which is often served with a side of roasted vegetables. You can also find delicious burgers, pizzas, and other comfort food at local restaurants.

Destinations nearby

Best Ashland, OR holiday rentals with a balcony

Hot Tub | Sauna |Firepit |Sleeps 6! - Ashland, OR
10 5 reviews
Ashland, OR
18/09 – 20/09
791 €/nighttotal: 1582 € (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.
"Enchantment"  Medford, Oregon - Ashland, OR
10 36 reviews
Ashland, OR
27/06 – 04/07
382 €/nighttotal: 2674 € (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.
The Dogwood Suite At Tudor House Vacation Rentals - Ashland, OR
9.4 201 reviews
Ashland, OR
15/10 – 19/10
184 €/nighttotal: 736 € (4 )

The Dogwood Suite At Tudor House Vacation Rentals

1 1
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.
Whimsy On B- 1 Block To Downtown Ashland - Ashland, OR
Ashland, OR
26/08 – 27/08
493 €/nightfor 1 night

Whimsy On B- 1 Block To Downtown Ashland

2 3
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.

Best pet friendly Ashland, OR holiday rentals

Among the 203 accommodations in Ashland, OR, here are the 4 best pet 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
1210 €/nighttotal: 6050 € (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.
Oak Street Studio - Ashland, OR
9.6 355 reviews
Ashland, OR
26/08 – 27/08
240 €/nightfor 1 night

Oak Street Studio

1 3
apartment , Ashland
The Oak Street Studio is situated on Water Street, just a few hundred metres from Lithia Park and the renowned theatres, making it a convenient base for exploring Ashland's cultural heart. The studio has received excellent ratings for its location, cleanliness, and overall user experience.
This self-catering apartment comfortably accommodates four guests with a king-size bed in the bedroom and a queen-size pull-out sofa in the living area. The studio includes parking, Wi-Fi, a TV, a kitchenette with a microwave and a full-size fridge, and a work-friendly space with a desk and a dining table.
Meadowsweet Farm- Sleeps 18, Outdoor Kitchen - Ashland, OR
Ashland, OR
07/10 – 12/10
687 €/nighttotal: 3435 € (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.
The Ashland Social | Guest Studio - Ashland, OR
10 26 reviews
Ashland, OR
10/07 – 12/07
311 €/nighttotal: 622 € (2 )

The Ashland Social | Guest Studio

1 2
studio , Ashland
This studio apartment is located just 0.4 kilometres from Ashland Plaza, placing you within easy reach of the city's main attractions, restaurants, and shops. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has a private entrance and can comfortably accommodate two guests. It features a kitchenette with a fridge, microwave, and other appliances, as well as Wi-Fi, heating, and parking.
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