Family-friendly vacation rentals in Jacksonville

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Top-rated family-friendly rentals in Jacksonville

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

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Guest favorite

Guest suite in Jacksonville

4.84 out of 5 average rating, 269 reviews

Claudia's Retreat Sanctuary

Retreat here on my 6 acres of madrone forest with pastoral views, 2 meditation labyrinths- yet only 3 miles to the quaint, historic town of Jacksonville, Oregon, home of Britt Festival, 35 minutes to Ashland and 1.5 hours to Mt. Shasta or Crater Lake. This guest suite in the lower level of my house and has uphill access to the hot tub by the garden. Book a Sacred Sound bath session with Tibetan and crystal bowls & Paiste gongs for $70 during your stay. Massage chair available too. Simply divine!

Sep 4 – 11

ﺩ.ﺇ317 per night

Guest favorite

Guest suite in Jacksonville

4.91 out of 5 average rating, 189 reviews

2-bedroom suite, only 1 mile to Jacksonville

Family and Senior friendly In Jacksonville, 1 mile to town. Cozy, quiet, scenic, isolated in the hills. Modern home with central A/C and heat, good cell signal, ceiling fans . Master Bedroom, key pad entry, King bed, fine sheets, TV with Amazon Prime, Bathroom, large towels, large jetted tub, double sink. Kitchenette with fridge-freezer, microwave, George Foreman grille, double burner, coffee pot, toaster, and blender. Adjacent bedroom Queen bed and desk with power strip. Private entry door.

Aug 28 – Sep 4

ﺩ.ﺇ519 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

ﺩ.ﺇ277 per night

Guest favorite

Guesthouse in Medford

4.92 out of 5 average rating, 344 reviews

The Greenwood Villa

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

Jul 12 – 19

ﺩ.ﺇ648 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

ﺩ.ﺇ469 per night

Guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 428 reviews

Comice Valley Inn (Sanitized Daily)

Health care professionals please ask about special rate for longer term rental. We disinfect all surfaces before and after new guests arrive. Rest assured. Comfortable, light, clean and airy private two bedroom upstairs guesthouse. Host on location in separate home. Fully equipped kitchen, with breakfast provided, makes this the perfect place for overnight or an extended stay. Neighborhood is quiet and shopping and dining are not far away. Two bedrooms make this a perfect getaway for friends.

Dec 4 – 11

ﺩ.ﺇ376 per night

Superhost

Cabin in Medford

4.85 out of 5 average rating, 102 reviews

Woodland Cottage near Jacksonville Dog Friendly

It seems remote, so your nervous system relaxes on 60 acres in nature's stillness, yet it's only 10-minutes drive to Jacksonville or Medford; 25-min to Ashland. Long stays welcome. Our sanctuary has modern comfort & convenience, a king + queen bed, 2 sofabeds, full kitchen, TV, large library + views. Our land supports evergreens, gardens, ranch critters (chicken, dogs), a shallow pond, hilly hikes to BLM trails, peaceful places to hang out. We welcome Canine Companions ($30/week fee) & Kids.

Sep 22 – 29

ﺩ.ﺇ464 per night

Guest favorite

Guesthouse in Medford

4.85 out of 5 average rating, 118 reviews

Lotus 2-Peaceful-Well Stocked-W/D-Walk to Park

-No Checkout Chores- Lotus Studio 2 is such a comfortable and relaxing place to wind down after exploring our beautiful area. The full kitchen is equipped for your cooking needs. It has a Keurig, coffees, teas, creamers and sugar, cooking oil and spices. Vaulted ceiling with a ceiling fan. The bathroom is a good size with a jacuzzi tub/shower. The walk-in closet has an energy efficient washer/dryer with laundry supplies included. Located 2 blocks from a major park-Fitchner Mainwaring.

Aug 5 – 12

ﺩ.ﺇ407 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

ﺩ.ﺇ513 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

ﺩ.ﺇ358 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

ﺩ.ﺇ535 per night

Guest favorite

Camper/RV in Medford

4.96 out of 5 average rating, 202 reviews

Backyard oasis w/king bed, full kitchen!

Come relax in a 2020 35ft RV, in a park like setting. With an island kitchen, comfy recliners and couch, walk around king bed, flat screen TVs, and electric fireplace, you can relax and unwind after a long day of sightseeing, or enjoy a cup of coffee or glass of wine out on the fully fenced patio area overlooking a large, beautiful backyard. Full hook-ups, great wifi, and fully functioning features make this SO much better than the standard hotel room.

Jul 23 – 30

ﺩ.ﺇ288 per night