Family-friendly vacation rentals in Ashland

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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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Guest favorite

Apartment 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.

Nov 21 – 28

G$31,934 GYD per night

Guest favorite

Apartment in Ashland

4.94 out of 5 average rating, 256 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

Aug 26 – Sep 2

G$26,146 GYD per night

Guest favorite

Guesthouse in Central Point

4.97 out of 5 average rating, 887 reviews

The West Wing Guest House

Located next to the main home, this detached guest house has a separate driveway/parking & hosts kitchen/living downstairs, with bedroom & bathroom upstairs. We are located 5 miles from Jacksonville, home of the Britt Festival & the best local wineries. About 20 minutes south is the town of Ashland, well known for the Shakespeare Festival. Downtown Central Point is just a mile away, where you will find the renowned Rogue Creamery. The house is also only 10 minutes from the Rogue Valley Airport.

Jul 11 – 18

G$15,418 GYD per night

Guest favorite

Home in Ashland

4.91 out of 5 average rating, 197 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

Jan 11 – 18

G$43,559 GYD per night

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 512 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.

Dec 2 – 9

G$28,591 GYD per night

Guest favorite

Camper/RV in Ashland

4.88 out of 5 average rating, 923 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.

Jul 23 – 30

G$11,899 GYD per night

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 709 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!

Sep 29 – Oct 6

G$19,966 GYD per night

Guest favorite

Camper/RV in Talent

4.94 out of 5 average rating, 291 reviews

Peaceful, artistic Airstream with amazing 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.

Jul 22 – 29

G$16,290 GYD per night

Guest favorite

Guesthouse in Ashland

4.9 out of 5 average rating, 340 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!

Feb 1 – 8

G$29,805 GYD per night

Guest favorite

Cottage in Talent

4.75 out of 5 average rating, 401 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

Oct 23 – 30

G$16,054 GYD per night

Superhost

Guesthouse in Ashland

4.87 out of 5 average rating, 127 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!

Jan 8 – 15

G$24,498 GYD per night

Guest favorite

Apartment in Ashland

4.88 out of 5 average rating, 724 reviews

Clean, Stylish Apt w/kitchen. block from Downtown

92½ Church Street. A private apartment with a large bedroom, full kitchen, bath with shower. Vintage styling with loads of special touches, ONE BLOCK from downtown. All the comfort of home and so close to the action. Large yard. Permitted. (Ashland City Permit: 15-237). 2020 Update: We have adopted the recommended Covid-19 Cleaning Guidelines.

Oct 28 – Nov 4

G$26,277 GYD per night