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Ashland, OR vacation rentals
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Best Vacation rentals and Airbnb offers in Ashland, OR

Top Vacation Rentals for Families in Ashland, OR

Booking a family-oriented vacation rental in Ashland, OR keeps you close to top city attractions for a stress-free getaway.

Courtside Cottage - Walkscore 93 - Dog Friendly - Ashland, OR
10 318 reviews
Ashland, OR
09/17 – 09/23
$384/nighttotal: $2304 (6 )

Courtside Cottage - Walkscore 93 - Dog Friendly

1 2
cottage , Ashland
This cottage is located in Ashland's Historic Railroad District, a short 10-minute walk from the Ashland Library and the Oregon Shakespeare Festival.
The one-bedroom cottage comfortably sleeps four guests and offers modern amenities like a full kitchen, a private patio, and free Wi-Fi.
1907 Charmer, Perfect Downtown Location, So Clean! - Ashland, OR
9.5 187 reviews
Ashland, OR
06/20 – 06/23
$555/nighttotal: $1665 (3 )

1907 Charmer, Perfect Downtown Location, So Clean!

1 5
apartment , Ashland
This 3-bedroom house is conveniently located in Ashland's Historic Downtown District, just a 5-minute walk from the Oregon Shakespeare Festival and the Ashland Library. It has consistently received excellent ratings for location, cleanliness, and user experience.
The 1270 square foot home offers a full kitchen, laundry facilities, two bathrooms, a dining area, and a coffee/tea maker. Guests can enjoy a private garden, a spa, and parking, and can bring their pets along.
Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly - Ashland, OR
10 66 reviews
Ashland, OR
09/05 – 09/07
$474/nighttotal: $948 (2 )

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

3 2
apartment , Ashland
This Ashland vacation home is conveniently located within a 15-minute walk of Lithia Park, the Oregon Shakespeare Festival, and several theaters.
This 1,590-square-foot house features three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, Jacuzzi, patio, garden, and free Wi-Fi.
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
09/05 – 09/07
$1532/nighttotal: $3064 (2 )

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 2
apartment , Ashland
This Ashland apartment rental, located in the Siskiyou-Hargadine Historic District, is a short walk from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library.
This 2,800-square-foot, six-bedroom residence sleeps twelve guests and features a fully equipped kitchen, a jacuzzi, a terrace, a garden, and free Wi-Fi.

Best Ashland, OR vacation rentals with parking

Manor Hill Haven Hot Tub & Accessible Features - Ashland, OR
10 1 review
Ashland, OR
06/25 – 06/26
$499/nightfor 1 night

Manor Hill Haven Hot Tub & Accessible Features

2 3
house , Medford
Manor Hill Haven, a 2-bedroom vacation home, is located 5 miles from Rogue Valley International-Medford Airport and 11 miles from the Oregon Shakespeare Festival, Lithia Park, and the Oregon Cabaret Theatre.
This 1600 square foot residence accommodates up to 9 guests with air conditioning, a Jacuzzi, a balcony, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, offering free Wi-Fi and private parking.
Pioneer Vacation Rentals - Pioneer Craftsman House - Ashland, OR
8.5 2 reviews
Ashland, OR
08/08 – 08/10
$593/nighttotal: $1186 (2 )

Pioneer Vacation Rentals - Pioneer Craftsman House

3 4
house , Ashland
This Craftsman-style vacation home is located in Ashland, Oregon, a 15-minute walk from Lithia Park and 1.3 miles from Southern Oregon University, offering easy access to the Oregon Shakespeare Festival and other Ashland attractions.
This 1800-square-foot house features three bedrooms, two bathrooms, and accommodates up to eight guests, boasting a fully equipped kitchen, private parking, a sun terrace, and welcome amenities like wine and chocolates.
Hot Tub | Sauna |Firepit |Sleeps 6! - Ashland, OR
10 5 reviews
Ashland, OR
06/20 – 06/21
$624/nightfor 1 night

Hot Tub | Sauna |Firepit |Sleeps 6!

2 4
apartment , Ashland
This Ashland vacation rental is conveniently located near Lithia Park and the Oregon Shakespeare Festival, with easy access to Grizzly Peak and Weisinger Family wineries.
The two-bedroom, three-bathroom home sleeps six guests and boasts a gourmet kitchen with a wine fridge, a jacuzzi, sauna, and a private terrace with valley views, plus nearby access to hiking, mountain biking, and the RRRink.
Escape To Manor Hill Haven! Accessible 2br Retreat With Hot Tub, Modern Comfort & Mountain Views. Perfect For Families, Couples & Business Travelers. - Ashland, OR
10 7 reviews
Ashland, OR
06/25 – 06/26
$522/nightfor 1 night

Escape To Manor Hill Haven! Accessible 2br Retreat With Hot Tub, Modern Comfort & Mountain Views. Perfect For Families, Couples & Business Travelers.

2 3
apartment , Medford
This East Medford vacation rental is conveniently located near Asante hospital (1 mile), Rogue Valley Manor (0.4 miles), and Rogue Valley Mall, providing easy access to downtown Medford, Jacksonville, and Ashland.
The two-bedroom, two-bathroom home offers wheelchair accessibility, an EV charger, a large deck with a hot tub and mountain views, and accommodates up to six guests, featuring a modern, open floor plan with a fully equipped kitchen and amenities including a Jacuzzi, garden, and pet-friendly accommodations.

Frequently Asked Questions about vacation rentals in Ashland, OR

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

    Ashland is full of interesting places! You can't miss the Oregon Shakespeare Festival, of course. The Lithia Park is beautiful and offers great views of the city. If you're looking for something a little different, head to the Ashland Art Center or the Southern Oregon Historical Society Museum. And don't forget about the nearby Crater Lake National Park, about a 2-hour drive from Ashland.
  • What are the best Airbnb and vacation rentals in Ashland, OR?

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

    The Bear Creek Greenway is a popular choice for both walking and cycling. It runs along Bear Creek and offers beautiful views of the surrounding mountains. For a more challenging ride, try the Emigrant Lake Loop, which takes you around Emigrant Lake and through the nearby forest. And if you're looking for a shorter walk, the Lithia Park loop is a great option.
  • 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 for outdoor activities. You can hike, bike, and fish in the surrounding forests and mountains. There's also great skiing and snowboarding at Mount Ashland in the winter. If you're looking for something more relaxed, you can go kayaking or paddleboarding on the Rogue River.
  • What are the best vacation rentals with a pool in Ashland, OR?

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

    You can easily reach Medford, about a 20-minute drive from Ashland. It's a larger city with more shopping and dining options. You can also visit Jacksonville, a historic gold-mining town about 15 minutes away. For a longer trip, you can head to Crater Lake National Park, about a 2-hour drive from Ashland.
  • What are the best rentals for families and kids in Ashland, OR?

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

    Most vacation rentals in Ashland will have basic amenities like a kitchen, bathroom, and bedrooms. Many also offer things like Wi-Fi, laundry facilities, and outdoor spaces. Some even have hot tubs or fireplaces. You can usually find rentals with specific amenities by searching online or contacting a local rental agency.
  • 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 most popular time to visit, with warm weather and plenty of outdoor activities. If you're interested in the Oregon Shakespeare Festival, the summer is the time to go. Fall is also beautiful, with colorful leaves and cooler temperatures. Spring is a good time to visit if you want to avoid the crowds and enjoy the wildflowers.

Destinations nearby

Best Vacation Rentals with Balconies in Ashland, OR

Enjoy your own private terrace with city skyline views at these vacation rentals in Ashland, OR.

The Dogwood Suite At Tudor House Vacation Rentals - Ashland, OR
9.4 200 reviews
Ashland, OR
08/08 – 08/10
$288/nighttotal: $576 (2 )

The Dogwood Suite At Tudor House Vacation Rentals

1 4
apartment , Ashland
This one-bedroom apartment is conveniently located in Ashland's Siskiyou-Hargadine Historic District, just a short walk from Southern Oregon University, the Ashland Library, and the Oregon Cabaret Theatre. It has earned excellent ratings for location, cleanliness, and overall user experience. This 800-square-foot rental comfortably sleeps five guests. Amenities include a fully equipped kitchen, a private terrace or balcony, a garden, a spa, and parking. Enjoy the convenience of a washer and dryer, free Wi-Fi in public areas, and a TV with a DVD player.
Swank Suites | King With Lux Tub - Ashland, OR
Ashland, OR
09/17 – 09/23
$306/nighttotal: $1836 (6 )

Swank Suites | King With Lux Tub

1 2
apartment , Ashland
This downtown Ashland apartment rental is one block from a grocery store and coffee shop, two blocks from an escape room, and within walking distance of the Oregon Shakespeare Festival and Lithia Park.
This 300-square-foot unit features one bedroom, two bathrooms, a king-size bed, a kitchenette with a microwave and mini-refrigerator, a private outdoor lounge, high-speed 5G internet, and accommodates two guests.
Xl Premier Suite - Ashland, OR
9.4 3 reviews
Ashland, OR
09/05 – 09/07
$345/nighttotal: $690 (2 )

Xl Premier Suite

1 2
apartment , Ashland
This Premier Suite, located in Ashland's Historic Railroad District, is one block from a grocery store and coffee shop, and within walking distance of downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens.
This 400-square-foot first-floor unit features a king-size bed, a kitchenette with microwave and mini-refrigerator, a private balcony, a large jetted tub, high-speed 5G internet, and accommodates two guests.
Barclay Klum House By Wanderlodges - Ashland, OR
9.4 11 reviews
Ashland, OR
09/05 – 09/07
$636/nighttotal: $1272 (2 )

Barclay Klum House By Wanderlodges

2 2
apartment , Ashland
The Barclay Klum House by WanderLodges is located in Ashland, a short walk from the Oregon Shakespeare Festival and close to the Schneider Museum of Art. This 1,500 square foot apartment features two bedrooms, one bathroom, and can accommodate up to seven guests, making it ideal for families or groups visiting the area.

Neighborhoods and points of interest in Ashland, OR

Our Favorite Pet-Friendly Vacation Rentals in Ashland, OR

Discover dog-friendly vacation rentals in Ashland, OR situated perfectly for city walks and nearby dog parks.

Charming House Two Blocks From Downtown Ashland - Ashland, OR
9.4 10 reviews
Ashland, OR
09/05 – 09/07
$362/nighttotal: $724 (2 )

Charming House Two Blocks From Downtown Ashland

2 2
apartment , Ashland
The Serendipity House is centrally located in Ashland, Oregon, two blocks from restaurants, shops, and theaters, offering easy access to the Oregon Cabaret Theatre and Allen Elizabethan Theatre.
This two-bedroom, one-bathroom home sleeps four guests and features a fully equipped kitchen with a complimentary coffee bar, air conditioning, a private garden, parking, and high-speed internet access.
Apartment Close To Downtown With Parking Included. - Ashland, OR
9.2 7 reviews
Ashland, OR
06/19 – 06/20
$198/nightfor 1 night

Apartment Close To Downtown With Parking Included.

1 1
apartment , Medford
This Medford City Center apartment is conveniently located within a 10-minute walk of Alba Park, the Medford Carnegie Library, and Medford City Hall, with the Children's Museum and Vogel Plaza a short 15-minute walk away.
This 500-square-foot rental offers one bedroom, one bathroom, sleeps two guests, and includes free WiFi, a Smart TV, in-unit laundry, designated parking, and a kitchen equipped with a refrigerator, microwave, oven, and stovetop.
Cozy Santa Feinspired 2br Retreat With Queen Beds, Sofa Sleeper, Soaking Tub, Fireplace, And Large Fenced Backyard. Great Location Near Medford, Jacksonville Wineries, And Ashland. - Ashland, OR
Ashland, OR
07/02 – 07/06
$366/nighttotal: $1464 (4 )

Cozy Santa Feinspired 2br Retreat With Queen Beds, Sofa Sleeper, Soaking Tub, Fireplace, And Large Fenced Backyard. Great Location Near Medford, Jacksonville Wineries, And Ashland.

3 5
apartment , Medford
This Santa Fe-inspired 3-bedroom house in Medford offers a quiet neighborhood setting with easy access to downtown Medford, Historic Jacksonville (5 miles), and Ashland (12 miles).
This 960 sq ft retreat accommodates up to 6 guests with a fully stocked kitchen, a large soaking tub, a fenced backyard, in-home laundry, fast WiFi, and driveway parking for 2-3 vehicles.
One Bedroom One Bathroom Studio With Full Kitchen And Stunning Patio. - Ashland, OR
10 2 reviews
Ashland, OR
09/05 – 09/07
$372/nighttotal: $744 (2 )

One Bedroom One Bathroom Studio With Full Kitchen And Stunning Patio.

1 2
studio , Ashland
This Ashland cottage rental is located in the Historic Railroad District, a 5-9 minute walk from the Ashland Library and Oregon Cabaret Theatre, and an 11-13 minute walk from Lithia Park and Ashland Creek.
The one-bedroom, one-bathroom dwelling sleeps two guests and includes amenities such as Wi-Fi, air conditioning, and a dryer; nearby attractions include the Weisinger Family Winery and US Cellular Community Park.
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