Kid-friendly vacation rentals in Jackson County

4.94 out of 5 average rating, 277 reviews

The Woody House

This lovely renovated 3 bedroom/1 bath home offers modern living with charm. Located in a quiet neighborhood in tree-lined Old East Medford, this home-away-from-home is located near Southern Oregon's many attractions: Ashland’s Oregon Shakespeare Festival, Jacksonville’s Britt Festival, over 40 area wineries (2 within 4 miles), Crater Lake, and the Rogue River. This bright and cheerful home features a well-appointed living room, dining area, fully-equipped kitchen, three bedrooms (one doubles as an office), full bath, and large laundry room. There is also private parking with a garage, a front yard and private back patio/garden offering space for barbeques and outside dining right off the kitchen. The home retains much of its original character but everything has been completely updated. This quiet home offers newly refinished hardwood floors throughout, open living space, and lots of natural light. The freshly remodeled kitchen provides loads of storage space, all new appliances, and everything for the home chef. This convenient location allows for easy walks to the cinema, coffee shops, growler pubs, bakeries, grocery stores and parks. This property is situated near (just a short bike ride) both Asante Rogue Regional Medical Center and Providence Medford Medical Center. It’s also 5 miles from Rogue Valley International Airport. Convenience, comfort & charm. We welcome our next guest!

4.92 out of 5 average rating, 116 reviews

An elevated view displays the spacious great room featuring rustic wooden beams and a cozy seating area with leather sofas. Large windows invite natural light, while the open layout connects to a modern kitchen with wooden cabinetry. A sliding door leads to an outdoor deck.

Farm stay in Days Creek

Family Retreat- Barn Complimentary Farm Breakfast

Private House 2 kitchens, fully stocked, 2 Full bathrooms , 4 Private bedrooms,Bonus Kids Loft with 2 Twins 2 kids futons There is a memory foam sofa bed in the family room on one side. This Duplex joins together via a Sliding Barn Door into over 3000 Sq Feet Of Grand Rustic Décor. A great room with 20’ ceilings for gathering after a long day of play. We are dog friendly with plenty room to roam. Enjoy 2 private creek side Decks with views of the farm. We are dog friendly but Do Not allow CATS

4.98 out of 5 average rating, 492 reviews

The exterior of The Ashland Cottage is shown, featuring a welcoming sign amidst lush greenery. The cottage’s blue siding and distinctive architectural details are highlighted, while a paved walkway leads to the front entrance, framed by natural foliage.

Guesthouse in Ashland

Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

4.81 out of 5 average rating, 120 reviews

The exterior of a two-story green house is displayed, featuring a central entrance door framed by white trim. Colorful red foliage from nearby trees enhances the welcoming atmosphere. A clear blue sky provides a bright backdrop to the well-maintained landscaping.

Home in Ashland

Street Level Flat in great Downtown Location "A"

This is a beautiful new 3 bedroom flat with oak hardwoods floors, granite counters, and new appliances. There is a laundry room with a washer and dryer. We offer a cozy living room to relax after your busy day with a sleeper sofa, flat screen TV, and air conditioning for those warm days. There is a fully equipped kitchen with stainless appliances, microwave and dishwasher. This flat is located in a prime location, a 5 minute walk to the popular Shakespeare Festival, restaurants and shops.

A spacious living area is highlighted by a large flat-screen TV mounted on the wall. Comfortable seating arrangements are complemented by a decorative area rug. Natural light floods the room through a front door and windows, enhancing the inviting ambiance of the space.

4.8 out of 5 average rating, 207 reviews

Common Area! Near Rogue X, 3 king beds 82" 4k tv

Huge grassy common area! Big 4k TVs. House is a large 3 bedroom in a nice neighborhood. Must be respectful of neighbors. No dogs left outside barking. There is an HOA at this house and disruptive behaviors are reported and fined. Guest pays all assessed fines! No outside music, no fireworks. This is a beautiful family oriented neighborhood backing up to a Huge common grassy area. There isn't any playground equipment but perfect for Frisbee, soccer, etc. Please treat it respectfully

4.99 out of 5 average rating, 582 reviews

A spacious living room is presented with stylish furnishings, including a gray sofa and a patterned area rug. Natural light filters through the large windows. A spiral staircase leads to the loft above, while double doors open to the outdoor space.

Guesthouse in Ashland

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.

4.93 out of 5 average rating, 163 reviews

The exterior of the home is presented with a well-kept lawn and landscaped garden beds. A large driveway leads to a two-car garage. A vibrant tree provides a splash of color against the neutral siding of the house, while sunlight filters through the leaves.

Home in Central Point

Ideal & quiet location, 3BR+office, perfectly cozy

Kid friendly, Inviting & Comfortable, 3BR 2BA + office in a clean and safe neighborhood. All the comforts of home will meet you at our door in the peaceful town of Central Point, OR. Here you'll find excellent local restaurants, shops, and parks that will make your stay enjoyable. Less than a mile from Interstate 5, its a great location for travelers. A quick 15 minute drive to Jacksonville, 25 mins to either Ashland or Grants Pass, Central Point is an ideal spot for both work and play.

5 out of 5 average rating, 165 reviews

A wooden dining table is set with a decorative yellow bowl. Large windows provide a view of the surrounding forest, allowing natural light to brighten the space. Green plants are visible nearby, enhancing the connection to the outdoors.

Home in Gold Hill

Hygge Hideaway. A home for rest and adventure

In Scandinavia, "hygge" represents contentment & coziness. Settle into this sun-soaked, mountain-side, madrone forest & valley view home for relaxation on the deck, wine by the fire, & mineral baths. This solar powered home has easy access to outdoor adventures. Options include Laundry, Wood Stove (fire logs avail $), & fully equipped Kitchen. Whether you're looking for a getaway, family event, road stop, or retreat - you're welcome here. Pets require PRE-APPROVAL.

4.87 out of 5 average rating, 101 reviews

A tiny home exterior is depicted, featuring a sleek metal façade complemented by warm wood accents. A comfortable seating area with cushions is positioned on the porch. A hot tub is also visible, inviting relaxation under the sun.

Tiny home in Medford

Broken Chair Ranch Bungalow

Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our tiny home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit near the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

A spacious backyard is showcased, featuring a covered patio with comfortable seating arrangements. Lush green grass surrounds the area, complemented by a wooden fence and a small play structure. Sunlight filters through the patio, creating an inviting outdoor space for family moments.

4.95 out of 5 average rating, 108 reviews

Voted Guest Favorite/Fast Wi-Fi/Hiking/Shopping.

Modern millennial dream! Stunning , bright & modern home. If you’re looking for that Instagram worthy spot, look no further! The living area boasts a floor to ceiling hand-painted mural for that perfect family photo backdrop. Each room caters to every age from young to seasoned. The open concept living room boasts a floor to ceiling mural of the mountains and comes complete with a gas fireplace.

A comfortable living area features a gray couch adorned with decorative pillows and a cozy blue chair. A simple white console table is positioned beneath a mounted television, with artwork displayed on the wall. Natural light streams through the window, highlighting the wood-like flooring.

4.84 out of 5 average rating, 242 reviews

Trailer parking, king bed, great for guests/pets!

Great location-directly across from North Medford High School. Newly renovated house inside and out! We created this house with comfort in mind-cozy pillow-top beds, super fast wi-fi, and 2 tv’s with Netflix, Disney and Hulu apps, new couch, granite countertops with a great table to enjoy a meal or a cup of coffee!