Kid-friendly holiday rentals in Ashland

4.94 out of 5 average rating, 276 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!

4.97 out of 5 average rating, 111 reviews

Home in Grants Pass

Cottage in the Heart of Grants Pass w/Hot Tub

Have fun with the whole family at this stylish 2 story cottage. Just a few blocks from downtown shopping, eateries, and the famous Rogue River. Our cottage features a fully stocked kitchen including spices, coffee & pancakes! Our home is equipped with hyper allergenic materials and bedding. Enjoy board games, making music & singing on the karaoke machine. Enjoy the outdoor beauty of Southern Oregon around the fire pit or in the hot tub. Come relax & enjoy your stay in our Hometown Getaway!

4.98 out of 5 average rating, 487 reviews

Guest house 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, 118 reviews

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.

4.97 out of 5 average rating, 371 reviews

Home in Grants Pass

Charming Cottage, Walk To Downtown!

Newly remodeled 1910 cottage a few short blocks away from historic downtown! 1 bedroom and 1 loft both featuring brand new queen beds.The cottage is only two miles off of I-5 and within walking distance to some of the best restaurants, bars, and shops downtown has to offer. The living room features a 60in HDTV. The kitchen is equipped with dishes, glassware, pots and pans, a keurig and many other commodities . The Outdoor area includes a grill, picnic table as well as a fire pit. No pets.

4.8 out of 5 average rating, 203 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, 573 reviews

Guest house 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.

4.94 out of 5 average rating, 157 reviews

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.

4.89 out of 5 average rating, 288 reviews

Flat in Grants Pass

West Park Unit A

Located in the prime spot of the Riverside Park area, this 2-bedroom, 2-bathroom is newly built and designed to impress. The upscale and luxurious atmosphere will leave you feeling right at home. Only a 5-minute walk away from Riverside Park, Fairgrounds, Walking Bridge, and the Downtown Historical District, this location couldn't be any better. Despite its proximity to all these popular attractions, this spot remains quiet and private, making for a truly relaxing stay.

5 out of 5 average rating, 159 reviews

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.

4.95 out of 5 average rating, 104 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.