Holiday Rentals in Ashland, OR

203 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Ashland, OR holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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
NZ$924/nighttotal: NZ$1848 (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.
Barclay Klum House By Wanderlodges - Ashland, OR
10 8 reviews
Ashland, OR
15/10 – 19/10
NZ$665/nighttotal: NZ$2660 (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.
Charming Guest House - One Block From Downtown! - Ashland, OR
10 667 reviews
Ashland, OR
15/10 – 19/10
NZ$407/nighttotal: NZ$1628 (4 )

Charming Guest House - One Block From Downtown!

1 1
house , Ashland
This one-bedroom guest house is located just 0.8 kilometres from the centre of Ashland, a short walk from the Shakespeare Festival, Lithia Park and numerous restaurants and cafes.
The property offers a comfortable living space with a fully equipped kitchen, a spacious bathroom, a private deck and a loft bedroom, accommodating up to four guests.
Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly - Ashland, OR
10 66 reviews
Ashland, OR
26/08 – 27/08
NZ$997/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, OR holiday rentals with parking

Swank House On Main St In Ashland - Ashland, OR
10 5 reviews
Ashland, OR
15/10 – 19/10
NZ$809/nighttotal: NZ$3236 (4 )

Swank House On Main St In Ashland

2 1
house , Ashland
This Swank House property is situated on Main Street, Ashland, Oregon, within a 1.6km walk of Southern Oregon University and 1.6km from both the ScienceWorks Hands-On Museum and Lithia Park.
The 139 square metre (1496 square foot) dwelling offers two bedrooms, two bathrooms, and sleeps six, featuring a fully equipped kitchen, free Wi-Fi, and on-site parking.
Victoria Cellars. Cozy 1-brm Apt. In Amazing Medford. Wifi, Ac, Secluded. - Ashland, OR
10 1 review
Ashland, OR
27/06 – 04/07
NZ$222/nighttotal: NZ$1554 (7 )

Victoria Cellars. Cozy 1-brm Apt. In Amazing Medford. Wifi, Ac, Secluded.

1 2
apartment , Medford
This Medford apartment, ideally located for exploring the city and its surroundings, is within 3.2km of Lithia & Driveway Fields and 1.6km of Fichtner-Mainwaring Park.
This one-bedroom, one-bathroom flat offers 59 square metres of space, sleeping up to five guests and is close to Rogue Valley Mall and The RRRink.
20% Off Osf Tix In B&c Sections For Guests! 5-min Walk To Downtwn, Private Yard - Ashland, OR
9.9 103 reviews
Ashland, OR
15/10 – 19/10
NZ$389/nighttotal: NZ$1556 (4 )

20% Off Osf Tix In B&c Sections For Guests! 5-min Walk To Downtwn, Private Yard

1 1
cottage , Ashland
This charming cottage is located in Ashland's Historic Railroad District, just a short walk (less than 1 km) from the Ashland Library, Oregon Cabaret Theatre, and Allen Elizabethan Theatre. This well-rated property has received excellent reviews for its cleanliness, location, and overall experience.
The 37 square metre cottage can accommodate up to 3 guests and features a comfortable bedroom, a fully equipped kitchen, and a private garden with a patio. Amenities include air conditioning, free Wi-Fi, and a smoke-free environment, allowing you to relax and enjoy your stay.
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
NZ$2407/nighttotal: NZ$12035 (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.

Frequently asked questions about holiday rentals in Ashland, OR

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

    Ashland is home to the Oregon Shakespeare Festival, a world-renowned theatre company. You can also visit the Lithia Park, a beautiful park with a Japanese Garden and a stunning waterfall. For a day trip, drive to the nearby Crater Lake National Park, a breathtaking volcanic caldera with stunning views.
  • What are the best Airbnb and holiday rentals in Ashland, OR?

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

    The Ashland Greenway is a popular paved path that runs along the Bear Creek, great for walking or cycling. For a more challenging ride, try the Emigrant Trail, which winds through the foothills of the Siskiyou Mountains. If you're into mountain biking, there are plenty of trails in the surrounding forests.
  • 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 hiking, with trails ranging from easy strolls to challenging climbs. You can go fishing in the Rogue River or go kayaking on the lake. In the winter, there are opportunities for skiing and snowboarding at nearby resorts like Mount Ashland Ski Area.
  • What are the best holiday rentals with a pool in Ashland, OR?

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

    You can easily drive to Medford, the largest city in the region, which has a regional airport and a variety of shopping and dining options. Jacksonville, a historic gold rush town, is about 30 minutes away. For a longer drive, you can visit Crater Lake National Park, about 2 hours away.
  • 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 offer basic amenities like kitchens, bathrooms, and bedrooms. Many also have laundry facilities, Wi-Fi, and outdoor spaces like patios or balconies. Some rentals may also have amenities like hot tubs, fireplaces, or even private pools.
  • 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 your interests. Summer is popular for the Oregon Shakespeare Festival and outdoor activities, while autumn offers beautiful foliage and cooler temperatures. Spring is a good time for hiking and wildflowers, and winter is ideal for snow sports.
  • What are the local dishes in Ashland, OR region?

    Ashland is known for its farm-to-table cuisine, with many restaurants featuring fresh, local ingredients. Some popular local dishes include trout, wild mushrooms, and berries. You can also find delicious craft beers and wines produced in the region.

Destinations nearby

Best Ashland, OR holiday rentals with a balcony

Grandview Of Ashland - Ashland, OR
10 4 reviews
Ashland, OR
20/08 – 22/08
NZ$1255/nighttotal: NZ$2510 (2 )

Grandview Of Ashland

1 2
house , Ashland
Grandview of Ashland, a one-bedroom house, is situated near Lithia Park and the Oregon Shakespeare Festival, approximately 2.9 kilometres from each.
This self-catering property sleeps up to 11 guests and boasts a fully equipped kitchen, three bathrooms, a Jacuzzi, sauna, private garden, free Wi-Fi, and free private parking; in-unit laundry facilities add further convenience.
Lithia Springs Resort - Ashland, OR
9.1 2281 reviews
Ashland, OR
07/10 – 12/10
NZ$1072/nighttotal: NZ$5360 (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.
The Dogwood Suite At Tudor House Vacation Rentals - Ashland, OR
9.4 201 reviews
Ashland, OR
15/10 – 19/10
NZ$367/nighttotal: NZ$1468 (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.
Savage Upon Siskiyou | Prime Osf Location - Ashland, OR
Ashland, OR
04/08 – 06/08
NZ$790/nighttotal: NZ$1580 (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.

Best pet friendly Ashland, OR holiday rentals

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

The Ashland Social | Entire Estate - Ashland, OR
10 12 reviews
Ashland, OR
15/10 – 19/10
NZ$1435/nighttotal: NZ$5740 (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.
Peace And Joy Mini Farm - Ashland, OR
9.4 204 reviews
Ashland, OR
07/10 – 12/10
NZ$273/nighttotal: NZ$1365 (5 )

Peace And Joy Mini Farm

2 4
gîte , Ashland
This Ashland countryside self-catering property is located 5 minutes (approximately 8km) from Ashland's town centre, providing easy access to the Oregon Shakespeare Festival and within a short drive of Mount Ashland Ski Area.
This pet-friendly holiday home offers two bedrooms, one bathroom, sleeping up to four guests, and features a mini-farm, BBQ area, on-site beauty salon, free parking, and excellent guest reviews.
5br Two Homes On Creek - Ashland, OR
9.0 2 reviews
Ashland, OR
07/10 – 12/10
NZ$712/nighttotal: NZ$3560 (5 )

5br Two Homes On Creek

5 4
apartment , Ashland
This tranquil five-bedroom, two-bathroom rental property offers direct access to Neil Creek and is situated on a private one-acre lot, conveniently located less than 1 kilometre from the M5 motorway and close to downtown Ashland.
This accommodation provides a giant wood barrel hot tub, two fully equipped kitchens, and an outdoor yoga space, perfect for up to 11 guests seeking relaxation and proximity to Ashland's attractions.
Cozy Ashland Getaway - Ashland, OR
9.8 1090 reviews
Ashland, OR
09/09 – 13/09
NZ$467/nighttotal: NZ$1868 (4 )

Cozy Ashland Getaway

1 1
apartment , Ashland
This charming bed and breakfast is situated on the outskirts of Ashland, just a short distance from Interstate 5 and a convenient drive to the town centre. It enjoys a peaceful setting with horses and pastures across the road and stunning mountain views, and it has received excellent ratings for its location, cleanliness and overall experience.
The house has an open plan layout, ideal for socialising with fellow guests. It offers a range of amenities, including a fully equipped kitchen, a garden with porches, parking, and a shared bathroom.
©2026 cozycozy.com