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

Centrally Located Downtown Historic Home W/parking - Ashland, OR
9.7 43 reviews
Ashland, OR
20/08 – 22/08
465 â‚¬/nighttotal: 930 â‚¬ (2 )

Centrally Located Downtown Historic Home W/parking

1 2
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.
Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.6 4 reviews
Ashland, OR
07/10 – 12/10
1120 â‚¬/nighttotal: 5600 â‚¬ (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.
Savage Upon Siskiyou | Prime Osf Location - Ashland, OR
Ashland, OR
20/08 – 22/08
625 â‚¬/nighttotal: 1250 â‚¬ (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.
"Enchantment"  Medford, Oregon - Ashland, OR
10 36 reviews
Ashland, OR
27/06 – 04/07
382 â‚¬/nighttotal: 2674 â‚¬ (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.

Best Ashland, OR holiday rentals with parking

Barclay Klum House By Wanderlodges - Ashland, OR
10 8 reviews
Ashland, OR
04/08 – 06/08
298 â‚¬/nighttotal: 596 â‚¬ (2 )

Barclay Klum House By Wanderlodges

1 2
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.
Hanna's House By Wanderlodges - Ashland, OR
Ashland, OR
18/09 – 20/09
362 â‚¬/nighttotal: 724 â‚¬ (2 )

Hanna's House By Wanderlodges

1 2
house , Ashland
This cottage is located 1 kilometre from Ashland's city centre, offering easy access to the Ashland Library, Oregon Cabaret Theatre, and Lithia Park.
This property accommodates two guests and features a kitchen with a dishwasher, air conditioning, a garden, an on-site restaurant, and parking, with Wi-Fi provided and laundry services available.
Whimsy On B | The Studio - Ashland, OR
Ashland, OR
04/08 – 06/08
232 â‚¬/nighttotal: 464 â‚¬ (2 )

Whimsy On B | The Studio

1 2
studio , Ashland
This studio apartment is situated in central Ashland, a short walk from the Oregon Shakespeare Festival and the Allen Elizabethan Theatre, and within 2 kilometres of Grizzly Peak Winery and Weisinger Family Winery.
The accommodation sleeps two guests and offers a king-size bed, a kitchenette with a toaster oven and hot plate, a private bathroom with a shower, air conditioning, Wi-Fi, and access to a garden and spa, with parking available.
2br Ashland Retreat: Steps To Shakespeare - Ashland, OR
9.4 3 reviews
Ashland, OR
04/08 – 06/08
564 â‚¬/nighttotal: 1128 â‚¬ (2 )

2br Ashland Retreat: Steps To Shakespeare

2 2
apartment , Ashland
This Ashland holiday home is ideally located in the Historic Railroad District, less than 0.8km from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Angus Bowmer Theatre.
The 149 square metre property boasts two bedrooms, three bathrooms, and accommodates four guests, offering a fully equipped kitchen, garden, balcony, and parking.

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

Barclay Klum House By Wanderlodges - Ashland, OR
9.4 11 reviews
Ashland, OR
18/09 – 20/09
409 â‚¬/nighttotal: 818 â‚¬ (2 )

Barclay Klum House By Wanderlodges

2 2
apartment , Ashland
This two-bedroom apartment is located in Ashland, Oregon, just a short walk from the Oregon Shakespeare Festival and close to other attractions such as the Schneider Museum of Art and Lithia Park. The 139 square metre property features a fully equipped kitchen, a private balcony with garden views, and parking for guests, making it ideal for families or groups of up to seven people.
Pioneer Vacation Rentals - Pioneer Craftsman House - Ashland, OR
8.5 2 reviews
Ashland, OR
04/08 – 06/08
501 â‚¬/nighttotal: 1002 â‚¬ (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.
Whimsy On B- 1 Block To Downtown Ashland - Ashland, OR
Ashland, OR
18/09 – 20/09
789 â‚¬/nighttotal: 1578 â‚¬ (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.
Lithia Springs Resort - Ashland, OR
Ashland, OR
07/10 – 12/10
492 â‚¬/nighttotal: 2460 â‚¬ (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.

Best pet friendly Ashland, OR holiday rentals

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

Swank Suites | Step Free  King - Ashland, OR
8.8 3 reviews
Ashland, OR
20/08 – 22/08
238 â‚¬/nighttotal: 476 â‚¬ (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.
Studio With King-size Bed - Ashland, OR
9.5 84 reviews
Ashland, OR
10/07 – 12/07
257 â‚¬/nighttotal: 514 â‚¬ (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.
Charming Carriage House In Ashland Near Downtown - Ashland, OR
9.8 10 reviews
Ashland, OR
25/08 – 26/08
222 â‚¬/nightfor 1 night

Charming Carriage House In Ashland Near Downtown

1 3
cottage , Ashland
This Ashland cottage, situated in the Skidmore Academy Historic District, offers easy access to Grizzly Peak and Weisinger Family Wineries (within a short driving distance, depending on the precise location within the district).
The one-bedroom property sleeps four, featuring a queen bed, sofa bed, and queen air mattress, a fully equipped kitchen with microwave and dishwasher, plus WiFi, air conditioning, and streaming services (HBO, Hulu, Netflix, Disney+).
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
206 â‚¬/nighttotal: 412 â‚¬ (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.
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