Pet-friendly holiday rentals in Ashland

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Ashland

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Ashland

4.86 out of 5 average rating, 285 reviews

Natty's Nook~Pet Friendly & 2 blks. fr. OSF

Natty's Nook is a Pet Friendly, 1 bedroom daylight basement apt. in our 1914 home w/ separate entrance. Tall Persons alert! ceilings are 6'-Guests assert it's a cozy Hobbit home! Totally furnished: fully stocked kitchen, range/oven, Frig., queen-sized bed, NEW full-size memory foam hide-a-bed, TV, WiFi, A/C, Sauna. Five min. walk to Plaza, OSF, Ashland Creek, Lithia Park & Five Star restaurants. This is a basement apt., you may hear light footsteps above. Fenced yard-One dog allowed w/ pet fee.

6–13 Mar

$213 SGD per night

Guest favourite

Home in Ashland

4.96 out of 5 average rating, 242 reviews

Secluded Forest Log House 15 minutes to Ashland

Beautiful hand built rustic log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to downtown Ashland, 20 minutes to Mt. Ashland Ski Area, and a five minute walk to Pacific Crest Trail. This home is the perfect quiet, serene getaway: close enough to Ashland to be convenient, yet completely secluded and private. Features include private covered parking, fully equipped kitchen, large private covered deck overlooking the forest, seasonal wood-fired sauna, and walking trails.

23–30 Nov

$248 SGD per night

Guest favourite

Tiny home in Grants Pass

4.97 out of 5 average rating, 201 reviews

Tiny Cabin in the Woods w/ Hot Tub and Firepit

Enjoy the charm of staying in a Tiny forest cabin, surrounded by nature and stylishly decorated with thoughtful décor accents. This is a tiny cabin, but has all the essentials that you need for your stay. Great location on the outskirts of town (8 mins from Merlin & 15 mins from Grants Pass). The closest access to the river is only 10 mins away at Matson Park! After a day of exploring, enjoy your hot tub with a wooded view or stargaze by the shared fire pit. Perfect Couples little getaway!

15–22 Mar

$200 SGD per night

Guest favourite

Guest house in Ashland

4.94 out of 5 average rating, 107 reviews

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

16–23 Jan

$147 SGD per night

Guest favourite

Cottage in Ashland

4.99 out of 5 average rating, 143 reviews

The Red Dragon House

Just a few minutes outside of Ashland, this unique and spacious property will put you in a rural setting with excellent views of the surrounding hills of the Rogue Valley. Located on 5.2 acres, with two security gates that are, remnants of a previous cannabis operation, the property affords ample privacy, and is invisible from the street, providing a perfect getaway for those that seek it. We are adjacent to I-5, so if road noise is an issue, this property may not be right for you.

19–26 Nov

$268 SGD per night

Guest favourite

Farm stay in Ashland

4.99 out of 5 average rating, 118 reviews

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

3–10 Sep

$164 SGD per night

Guest favourite

Cabin in Ashland

4.93 out of 5 average rating, 227 reviews

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin has remodeled upgrades and is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakepeare Fetival, Plaza shops, beautiful Lithia Park and Resturants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the pituresque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings!

23–30 Dec

$153 SGD per night

Guest favourite

Flat in Ashland

4.95 out of 5 average rating, 645 reviews

Modern Crash Pad | Pet Friendly | West Wing

NEW! Upgraded to KING bed!! A modern suite located steps away from the Ashland conference center and just minutes to downtown. Step into this light filled space which boasts stunning walk in shower, antique brass fixtures, and convenience kitchenette. Thoughtfully designed including heated bathroom tiles. Enjoy the breathtaking views of Grizzly Peak, and the local non-commercial airport. 1 pet welcome with fee. Note that we do not have a fenced yard. (#18-243).

7–14 Dec

$162 SGD per night

Guest favourite

Campervan/Motorhome in Ashland

4.88 out of 5 average rating, 920 reviews

Cozy camping close to town

The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, French press, hot water kettle, lending library, and games; this adorable camper is both functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

2–7 May

$80 SGD per night

Guest favourite

Guest house in Ashland

4.97 out of 5 average rating, 143 reviews

Manzanita Cottage

Enjoy staying in this newly-constructed cottage in the heart of Ashland's historic railroad district. Park your car and enjoy all that Ashland has to offer by foot. Easy walking distance to downtown shops and restaurants, OSF, Lithia Park and the Ashland Food Coop. Outdoor enthusiasts can start their mountain biking, running or hiking adventures right from their door. Your hosts can help to point you in the right direction. (Permit #: PA-2018-00531)

28 Oct – 4 Nov

$259 SGD per night

Guest favourite

Guest house in Central Point

4.94 out of 5 average rating, 708 reviews

BEE WELL Organic Spa Garden Studio

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

10–17 Aug

$153 SGD per night

Guest favourite

Guest house in Jacksonville

4.98 out of 5 average rating, 154 reviews

Starthistle Cottage in Applegate wine country

Rural cottage in the beautiful Applegate Valley. Peaceful with beautiful views of the landscape and wildlife. Closest lodging to Woodrat Mountain launch for paragliders & hang gliders. Nestled in the heart of the Applegate Wine Trail and the Southern Oregon Lavender Trail. Close to historical Jacksonville for the Britt Festival. Easy access to Applegate Lake and surrounding hiking trails.

17–24 Nov

$146 SGD per night