Kid-friendly vacation rentals in Ashland

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Top-rated kid-friendly rentals in Ashland

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

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Guest favorite

Home in Medford

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!

Guest favorite

Home in Medford

4.94 out of 5 average rating, 419 reviews

🌟 🥂 Medford’s BEST 📣 🌟 💕Clean, Modern, Private💕

Simple and clean, with a hidden, private driveway in a safe and secure area of North East Medford. This home is only a few minutes from Rogue Valley International- Medford Airport, plenty of shopping, grocery stores, city transit & local hospitals. Take a short drive to explore Crater Lake, Oregon’s only National Park or head over to Ashland & experience the Oregon Shakespeare Festival. Mountains, lakes & rivers nearby & the Oregon Coast is only 2 hours away. There’s something for everyone here!

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 484 reviews

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

Superhost

Home in Ashland

4.81 out of 5 average rating, 118 reviews

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.

Superhost

Home in Medford

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

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 571 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.

Guest favorite

Home in Central Point

4.94 out of 5 average rating, 157 reviews

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.

Guest favorite

Home in Gold Hill

5 out of 5 average rating, 158 reviews

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.

Guest favorite

Home in Medford

4.93 out of 5 average rating, 120 reviews

Comfy Cozy Casa

Relax with the whole family at this comfy and clean family friendly home centrally located in a cute residential neighborhood. Only minutes away from major shopping, food, and entertainment. This location makes for an easy stop over along I-5 on an Oregon road trip. Hiking trails are not far from this location, many guests stay here to check out Crater Lake National Park, and even some of the mountain lakes not far away.

Guest favorite

Home in Medford

4.95 out of 5 average rating, 103 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.

Superhost

Home in Medford

4.84 out of 5 average rating, 237 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!

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 167 reviews

Courtside Cottage - WalkScore 93 - Dog Friendly

The same cottage you've known and loved. Now we manage it ourselves. A sampling of previous reviews are in the photos. Named one of the Top Ten Traveler's Accommodations in Ashland by The Oregonian. Dogs always welcome. Please read all of the house rules and particulars regarding parking. Thanks!