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Family-friendly vacation rentals in Ashland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Ashland

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

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Loft in Hornbrook

4.94 out of 5 average rating, 374 reviews

The Green Arrow Loft

Situated right on the state line this studio apartment is nestled in its own little corner of the gorgeous Colestine Valley. We're located on 80 acres that adjoin the Cascade-Siskiyou National Monument to the north, perfect for a scenic hike or a casual stroll. Nature and wildlife abound, and though quiet and private the Loft is just five minutes off I-5 and 25 minutes from unique downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on pet and pool fees.

Rental unit in Ashland

4.94 out of 5 average rating, 266 reviews

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (low ceiling) Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Private parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Home in Ashland

4.91 out of 5 average rating, 221 reviews

Ashland Haus Retreat - 1 block from downtown!

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom. PA # PA-2017-01160

Guesthouse in Ashland

4.99 out of 5 average rating, 557 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Camper/RV in Ashland

4.89 out of 5 average rating, 966 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, hot water kettle, lending library, and games; this adorable camper is supremely functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland's picturesque downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

Guesthouse in Central Point

4.94 out of 5 average rating, 752 reviews

BEE WELL Organic Spa Garden Studio w/ Hot Tub

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!

Camper/RV in Talent

4.94 out of 5 average rating, 309 reviews

Peaceful Airstream with panoramic views

This beautifully rebuilt Airstream, makes for the perfect cozy getaway. Perched on its own terrace on a 5+ acre Italian style estate you'll be surrounded by spectacular views, an abundance of fine food, entertainment (including the world famous Shakespeare and Britt Festivals), nightlife, endless family-friendly and outdoor activities, day trips to destination wineries, redwoods and Crater Lake. 4 mi. from downtown Ashland and 13 mi. from Medford airport.

Guesthouse in Ashland

4.89 out of 5 average rating, 379 reviews

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

Cottage in Talent

4.76 out of 5 average rating, 426 reviews

" sweet little garden studio "

Nice little shady deck with rocking chairs. Very quiet and safe little neighborhood. Great location. Eight minutes to downtown Ashland and 15 minutes to downtown Medford. Comfortable little Studio. Great for one or two busy guest. If bringing an animal please lmk beforehand of what kind and size. Im allowing one well behaved animal. Must not be left behind and clean up is a must. Thank you for understanding.

Rental unit in Talent

4.87 out of 5 average rating, 458 reviews

Shady Grove Farm - Studio

This cute and private studio is spacious with a large bathroom, comfy queen bed plus single roll-away, flat screen TV/DVD, games, air conditioning, and a kitchenette with all the necessary cookware. It backs up to a large pond and grassy area. If it's booked, check out our garden cottage or the bunkalo (large canvass wall tent with a real bed). Only dogs under 15 lbs. are allowed in the studio.

Rental unit in Grants Pass

4.95 out of 5 average rating, 840 reviews

Peace on the Rogue river Studio

Beautiful park like setting on the Rogue river with a jacuzzi, swim spa two decks, fishing, yard games, hammock, barbecues, bicycles, kitchenette has Keurig With pods,a toaster oven, crock pot, small George Forman a portable two burner cook top , small skillet, one pot and most utensils to provide a meal. Minutes from Grants Pass, shopping, restaurants, and winery's.

Guesthouse in Ashland

4.86 out of 5 average rating, 138 reviews

ABBOTT'S COTTAGES- Egret

A cozy hideaway for two tucked into a private corner, the Egret is a perfect place to come home to after enjoying a night at theatre or a walk in the park. Spanish tiles and hand forged iron accents add to the ambiance of this special studio cottage. There are other cottages on the property if you are with a group looking for more than one house. Just let us know!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Ashland family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Tiny home in Grants Pass

4.96 out of 5 average rating, 102 reviews

River Rapids Home, stargazing from the hot tub!

Home in Ashland

4.89 out of 5 average rating, 9 reviews

Refurbished Barn house on 6 acres

Home in Grants Pass

4.97 out of 5 average rating, 290 reviews

Private Carriage House

Rental unit in Rogue River

4.96 out of 5 average rating, 53 reviews

Jaloma Woods, a forested retreat

Family- and pet-friendly home rentals

Bungalow in Ashland

4.99 out of 5 average rating, 100 reviews

Penthouse Suite, easy walk to downtown.

Guesthouse in Gold Hill

4.98 out of 5 average rating, 83 reviews

Rogue River Guesthouse: Rural river views near I-5

Home in Medford

4.82 out of 5 average rating, 295 reviews

Hillcrest 4br 6 bed, last minute ok, 75" Qled TV!!

Guest suite in Ashland

4.85 out of 5 average rating, 386 reviews

Jazzy B Suite~Historic, eco/dog friendly

Guest suite in Medford

4.92 out of 5 average rating, 218 reviews

Modern Lodging- Close to Airport/Fairgrounds/Expo

Cabin in Medford

4.86 out of 5 average rating, 105 reviews

Woodland Cottage near Jacksonville Dog Friendly

Home in Medford

4.92 out of 5 average rating, 198 reviews

🌟30 DAY-25%🌟PET FRIENDLY🌟PRIVATE🌟FENCED YARD🌟W/D🌟

Rental unit in Grants Pass

4.83 out of 5 average rating, 206 reviews

Great location to I-5 and city! King bed!

Family-friendly home rentals with a pool

Home in Grants Pass

4.83 out of 5 average rating, 18 reviews

Beautiful home on the Rogue river.

Guesthouse in Grants Pass

4.94 out of 5 average rating, 438 reviews

Sweet Vintage Cottage steps from Rogue River

Rental unit in Ashland

4.87 out of 5 average rating, 253 reviews

Winner 2023 Best of Ashland! Our Carriage House

Home in Grants Pass

4.89 out of 5 average rating, 434 reviews

Quiet neighborhood 3 BR w/ pool

Quick stats about vacation rentals that are family-friendly in Ashland

Total rentals
120 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
4.4K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi

Destinations to explore