Family-friendly vacation rentals in Ashland

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.

4.98 out of 5 average rating, 563 reviews

Charming cottage, walk to town.

Our guests arrive at The Ashland Cottage and their first words are almost always the same: "It's gorgeous!" That's because the cottage delivers what Ashland visitors want- comfort, charm and a walkable location just 10 minutes from downtown and OSF theaters. Though newly built, the cottage echoes the Craftsman character of our 1920s main residence. As a fully separate house with its own private entrance, it offers spacious living with high ceilings, abundant natural light and inspiring views.

A cozy living area features a brown leather sofa paired with a green armchair, arranged around a decorative rug. A flat-screen television is positioned against the wall, complemented by a large window allowing natural light. A potted plant adds a touch of greenery.

4.98 out of 5 average rating, 125 reviews

Historic carriage house close to downtown Ashland

Explore downtown Ashland in a private carriage house! This home was built in 1884 and is on the property of an historic Victorian. Full kitchen with stove, dishwasher and refrigerator. Pellet stove in the living room as well as wall vented heating. Enclosed yard. Separate bedroom and en suite with a tub/shower combo and washer and dryer. Off street parking. HBO and Netflix included. 10 minute walk to downtown Please note the only bathroom is through the bedroom. Dog friendly - no cats please

4.79 out of 5 average rating, 198 reviews

The cozy sleeping area features a twin bed adorned with a colorful blanket and decorative pillows. Brightly painted walls in warm hues reflect a sunset, while an air conditioning unit and a small window provide ventilation and natural light.

Tiny home in Ashland

Walk to town! Cozy Forest Teeny House

Escape to our charming teeny house, a custom-built 6' x 12' minimalistic camper just minutes from downtown Ashland and I-5. Perfect for solo travelers seeking a one-of-a-kind experience, this teeny house features a super comfy twin bed, and essential comforts of home. With a cute remote shared bathroom. It has a warm and welcoming feel of being secluded in the country yet just a 20-minute picturesque walk to town. Experience the unique charm of Ashland, Oregon in our one-of-a-kind teeny house.

4.96 out of 5 average rating, 182 reviews

A comfortable living room is furnished with two sofas and an armchair, arranged around a wooden coffee table. Soft pillows complement the seating. A lamp stands beside a wall, providing light, while artwork adorns the walls, adding a serene touch to the space.

Home in Phoenix

Phoenix Rising

Relax with the whole family at this peaceful home with a half acre backyard full of fruit and shade trees along with a gas BBQ. Games include board games, corn hole, outdoor Jenga. Several restaurants within walking distance. Wheelchair accessible park across the road at Blue Heron Park along Bear Creek Greenway. 3.8 mi. - Lithia & Driveway Fields 4.5 mi. - Rogue Regional Hospital 5.5 mi. - Medford Airport 5.9 mi. - Jackson County Expo 13 mi. - Shakespeare Festival 19 mi.- Mt Ashland ski area

4.97 out of 5 average rating, 514 reviews

The inviting living area showcases a stone fireplace as a focal point, complemented by a wooden mantel. Sunlight filters through large windows, illuminating a seating area with a comfortable chaise lounge and a wooden table. A rich area rug adds warmth to the hardwood floor.

Cottage in Ashland

Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

4.93 out of 5 average rating, 207 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!

5.0 out of 5 average rating, 104 reviews

Farm stay in Grants Pass

Cozy Wild West Covered Wagon next to River

Reconnect with nature in the breathtaking Applegate Valley while enjoying the comfort of our cozy covered wagon. Take a step back in time and create memories as our ancestors did on the Oregon trail in covered wagons. Escape the hustle and bustle of everyday life & unwind in our Paradise on the Applegate River. Enjoy the many nature trails that meander throughout the 11 acres on our farm. Say hello to all of the cute furry animals grazing on our pasture. Your adventure awaits!!

A spacious outdoor area features a crystal-clear swimming pool adjacent to a stone hot tub. Surrounding greenery and colorful flowers enhance the serene setting. Seating options are available nearby, with steps leading elegantly from the house to the poolside.

4.95 out of 5 average rating, 164 reviews

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

The entrance to the cottage is framed by a rustic trellis and surrounded by lush greenery. A wooden deck leads up to a white door, providing a welcoming access point. Sunshine filters through the leaves, adding a natural brightness to the scene.

5.0 out of 5 average rating, 300 reviews

Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. NEW: a high speed (240 volt) charger for EVs. You need an adapter.

The exterior of a guest house is shown, featuring a light yellow facade and large windows. A deck with white chairs and a table is visible, surrounded by green grass and landscaping stones. A flowering tree provides shade, complementing the serene outdoor space.

4.9 out of 5 average rating, 196 reviews

Mindy’s Ashland Hideaway

Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

Farm stay in Jacksonville

Red Barn in Wine Country

Luxury barn with a rustic feel on "Red Barn Farm" in Southern Oregon Wine Country. Our five-acre micro-farm is situated on the Applegate River exactly between Crater Lake & the Redwood forest. Our lush Applegate valley is a region of 19 artisan wineries. Walk to Red Lily Vineyard tasting room. This farmstay has a river swimming hole, friendly chickens, mini-goats & sheep, and a fire pit to spend dreamy evenings under the stars. Visit Wine Country Farm Stay dot com for more info!

4.91 out of 5 average rating, 110 reviews

A cozy log house features a red metal roof and is surrounded by tall trees and lush greenery. The structure showcases a covered porch area and a spacious, welcoming outdoor space. Sunlight filters through the trees, enhancing the serene forest setting.

4.97 out of 5 average rating, 320 reviews

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

Popular amenities for Ashland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 126 reviews

Guest suite in Ashland

RedTail Inn - Red McCall Suite | Sleeps up to 6

4.93 out of 5 average rating, 461 reviews

Guesthouse in Medford

The Greenwood Villa w/wood fire hot tub

4.84 out of 5 average rating, 121 reviews

An outdoor deck features a two-person hot tub and a barbecue grill. Wooden beams extend overhead, allowing natural light to illuminate the space. Surrounding trees create a natural backdrop, enhancing the connection with nature.

Cabin in Ashland

Bluemoon Vacation Rentals - Cabin 52

4.93 out of 5 average rating, 267 reviews

A light-filled living room features large windows and a skylight, enhancing the warm tones of the wood flooring. A cozy seating area includes a leather sofa and an armchair, accompanied by a small coffee table. A stylish wood stove adds a functional and aesthetic touch.

Cottage in Ashland

Vineyard Cottage-Winery, Hot Tub, Privacy

Guesthouse in Jacksonville

La Petite Maison + Spa

4.96 out of 5 average rating, 178 reviews

4.97 out of 5 average rating, 177 reviews

An A-frame home is nestled among tall trees, featuring a wraparound deck illuminated by string lights. The natural wood structure contrasts with the surrounding greenery as the sky transitions into twilight, creating a serene ambiance.

Cabin in Grants Pass

The Epic A - Charming 1960s A-Frame w/Hot tub

Guest suite in Jacksonville

A hot tub filled with clear water is positioned on a private deck, offering panoramic views of surrounding mountains and lush forest. Sunlight reflects off the water's surface, enhancing the tranquil setting, with a glimpse of a river in the distance.

The Birdhouse Retreat| Views & Hot Tub

4.83 out of 5 average rating, 279 reviews

4.98 out of 5 average rating, 119 reviews

A modern, single-story home sits beneath a bright sky, surrounded by tall trees. The structure features a covered wooden deck at the entrance, with large glass doors that open to an expansive outdoor space, creating a seamless transition between indoors and outdoors.

Home in Grants Pass

Rogue Reefs

Family- and pet-friendly home rentals

The exterior of the Serendipity House features a light-colored facade with a welcoming porch shaded by trees. Garden areas with stone pathways are present, enhancing the home's approachable charm. Large windows allow natural light to illuminate the inviting entrance.

4.88 out of 5 average rating, 179 reviews

Charming house two blocks from downtown Ashland

4.99 out of 5 average rating, 162 reviews

The exterior of a chic home is displayed, featuring white siding and a welcoming porch supported by wooden pillars. A neatly landscaped yard is visible, bordered by shrubs and rocks, with a garage on one side. Daylight enhances the inviting appearance of the property.

Home in Medford

Designer Home w/ Chef’s Kitchen

4.94 out of 5 average rating, 157 reviews

Neil Creek Cottage

A cozy studio room features a king-size bed with decorative pillows against a deep red accent wall. A small dining table with three stools sits nearby, facing an electric fireplace beneath a wall-mounted television. Light hardwood flooring adds warmth to the space.

4.98 out of 5 average rating, 281 reviews

Courtside Cottage - WalkScore 93 - Dog Friendly

4.98 out of 5 average rating, 119 reviews

Hotel room in Ashland

Swank Boutique Suites | King Suite | DT Ashland

4.91 out of 5 average rating, 169 reviews

Beautiful and peaceful cottage close to downtown

The exterior of a classic two-story home is framed by green foliage, with a welcoming front porch featuring two chairs. A neatly maintained pathway leads to the entrance, showcasing subtle architectural details and original fixtures.

4.91 out of 5 average rating, 274 reviews

Ashland Haus Retreat - 1 block from downtown!

4.89 out of 5 average rating, 887 reviews

A spacious bedroom features a comfortable bed with soft linens, accented by orange and neutral pillows. Large windows with decorative curtains allow natural light to flood the room. A wooden table and folding chairs provide additional seating, and a ceiling fan offers air circulation.

Apartment in Ashland

Clean, Stylish Apt w/kitchen. block from Downtown

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 283 reviews

A comfortable seating area is showcased with a vibrant red sofa, accompanied by a white chair. Colorful woven textiles adorn the walls and floor, adding cultural richness. Soft lighting highlights the warm tones of the decor, creating an inviting space for relaxation.

Apartment in Ashland

Mexico Apartment at Wood Hamlet, by Downtown

4.96 out of 5 average rating, 151 reviews

A charming two-story home is framed by lush green grass and mature trees. The exterior features a classic design with a combination of large windows, a welcoming porch, and a tasteful blend of light and dark siding. The sky is bright with scattered clouds.

Home in Central Point

Beautiful Country Home next to Jacksonville!

4.89 out of 5 average rating, 102 reviews

Home in Jacksonville

Luxury Mountain-Top Retreat | Sleeps 14

Guest suite in Grants Pass

An inviting swimming pool is set in a landscaped area, surrounded by palm trees and a wooden fence. The pool features a unique shape with a brick border and a small, rounded seating area nearby. Sun loungers are positioned adjacent to the water.

Cool Blue Waters-Guest Suite

4.93 out of 5 average rating, 114 reviews

4.87 out of 5 average rating, 260 reviews

Home in Medford

Big Pool, Great Room, Spa, Work Crews or Families

4.93 out of 5 average rating, 411 reviews

A long, covered balcony extends from the Loft, featuring a swinging seat for relaxation. The view showcases distant mountains and greenery, with trees lining the perimeter. The wooden floor adds a rustic touch, while the soft evening light creates a calming ambiance.

Loft in Hornbrook

The Green Arrow Loft

4.91 out of 5 average rating, 191 reviews

A fenced front yard is displayed, featuring a porch with two blue chairs and a small table. String lights are hung above, adding a warm touch. The entrance to the cottage is framed by two black shutters, leading into a bright and welcoming space.

Cottage in Central Point

Farm Cottage 1/2 Mile Outside Jacksonville