Family-friendly vacation rentals in Prineville

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Prineville

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Guest favorite

Guesthouse in Bend

4.97 out of 5 average rating, 542 reviews

Live the Pastoral Idyll in a Warm and Inviting Guesthouse

Located in a quiet, rural hamlet, this enchanting casita is quaint yet contemporary. Windows on all sides, combined with modern lighting, create a bright and welcoming space. Settle into a classic Adirondack chair and admire the bucolic landscape. Up to two Kids stay free! Our additional guest charge is waived for up to two children. Either adjust your reservation guest count just to reflect the adults in the group (minus up to two children) and message me the details of your party or send me a request and we can adjust the rate. The casita is an inviting newly remodeled space. The front living space has a fold down couch with all the bedding provided to turn this into a cozy second sleeping area. The wall mounted television has access to local cable, Netflix and Hulu. You can also rent a movie with Vudu without leaving the house! Just login or create an account and enjoy. The kitchenette has a full sized fridge to keep all of the famous Bend beer cold that you bring home to enjoy. Enjoy a cup of coffee or tea on us!! We have a Keurig and provide a selection of beverage choices for our guests. The casita also has a hot plate, toaster oven, microwave and BBQ and a selection of dishes & pots and pans if you feel like cooking during your stay. The bedroom has a very comfortable King size pillow top mattress, a dresser, night stands. Some hanging storage and a luggage rack. The room is easily large enough to accommodate a porta crib (we have on available for use) or additional small child's sleeping mat. We welcome well behaved pets to stay at our airbnb. We ask that pets stay off the furniture during your visit. Please enjoy the space. The patio area outside of the Airbnb is for our guests to enjoy. You are welcome to explore the pastures outside of the Airbnb. Please make sure you close any gates behind you, we have friendly horses who many be in the area and come to say hello. Our home is located on the property, but it is not physically connected to the Airbnb space. We get to meet many of our guests in the driveway as we are taking care of things outside. We are always available by text or phone. We have pets (dogs/cats/horses) who live on the property as well. Our Rottweiler, Mia is very friendly and is around frequently to see if she can make new friends with our guests. She always is looking for someone to give her a pet, be aware once you start petting her she really like to lean into people and can catch you off balance if your not prepared. Please let me know if you, or the pets traveling with you, have concerns with interactions with our dogs and we can make arrangements to have them more contained during your stay. Despite its rural setting, the house is only a few minutes by car from all of Bend's amenities. Closer to home, Cascade Village and the neighborhood of Tumalo are just a mile away. Hiking, biking, fishing and golf are popular activities. Looking for some provisions? Just 1 mile down Hwy 20 east towards Bend take a left on Robal road to access the cascade village shopping center. Groceries: Trader Joe’s, Food 4 Less, and Target are all located here. Trailhead liquor store just across Hwy 97 at Robal road (Oregon only sells beer and wine in the grocery store) Dining: Shinsei Sushi, Little Pizza Paradise, El Rancho Grande, Moose Sister’s, Olive Garden or cross Hwy 97 for Kefi fresh, Cracker Barrel & MOD pizza. Grab and go: Starbucks, Chipotle, Chick Fil-a, Taco DelMar, Togo’s, Jamba Juice. Or cross Hwy 97 for Black Rock Coffee Bar (try a cronut, their awesome!) To explore Central Oregon you will need a car. The Airbnb is a quick drive to many area attractions. In about 30 minutes or less you can be at Smith Rock, Mt. Bachelor, headed into the Cascade Lakes or many of the other hiking or Mountain bike trails in the area. The cute community of Tumalo is 1 mile west on Hwy 20. Stop in at the Bite, enjoy the sunshine, food trucks and a selection of local beer or hop across the street to Tumalo Cider and same their local cider in their new tasting room (Dry is my favorite). Keep going west on Hwy 20 and in less than 20 miles you will arrive in the picturesque community of Sisters where you can easily spend an afternoon exploring the shops and enjoying the magnificent view of the mountains.

Guest favorite

Guest suite in Prineville

4.93 out of 5 average rating, 242 reviews

Artsy Guest House Nestled in the Rimrock

This property is truly an oasis from the hustle and bustle of city life. When you arrive, the massive rimrock wall will greet you; it is home to abundant wildlife (owls, deer, coyotes oh my). Shrouded by silence, the trill of frogs will put you to sleep. Mornings start with sunrise over the Ochoccos and full views of the valley and the crooked river at its base. Take a hike at Smith Rock, visit the Painted Hills or find yourself headed to town (Bend: 45 min, Prineville: 10 min, Redmond: 25 min).

Guest favorite

Rental unit in Redmond

4.97 out of 5 average rating, 484 reviews

Smith Rock Contemporary

Epic views await at this new contemporary Airbnb suite. Situated atop Cinder Butte, with stunning views of Smith Rock, Mt. Hood, Mt. Jefferson and the Terrebonne valley. Enjoy this 800 sf apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A huge covered deck with magnificent views will make you feel right at home. Get your trip started off right with a gorgeous sunrise over Smith Rock.

Guest favorite

Home in Terrebonne

4.98 out of 5 average rating, 859 reviews

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Guest favorite

Chalet in Redmond

4.96 out of 5 average rating, 304 reviews

Wow Holy Cow Chalet

Wow Holy Cow! will be your first thought when you set foot into this knotty pine walled, sunlit filled chalet. Furnished with everything you need for a fun, family getaway. Channel Maria von Trapp while taking in the beautiful mountain views from the loft space. Have a drink on the deck while your kids search for frogs in the rock feature and shallow creek below. Grill a steak on the bbq and admire the deer who often pass by. Check our Instagram for vacation ideas @wowholycowchalet DCCA# 1453

Guest favorite

Home in Bend

4.94 out of 5 average rating, 244 reviews

Beautiful 10 acre farm stay in Tumalo!

Welcome to our family farm! Our lodging consists of a beautifully remodeled private wing and secluded patio and a beautiful, private fire pit to enjoy after a long day hiking or skiing! We also have added a Swedish barrel sauna with hot rocks to enjoy. It does wonders for your skin and soul! We provide luxurious robes!Our working farm is located on a quiet country road, sandwiched between Bend and Sisters. We also are now booking our outdoor space for small weddings and other celebrations.

Guest favorite

Farm stay in Prineville

4.93 out of 5 average rating, 385 reviews

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

With 2100 acres nestled against the Ochoco NF, our ranch is a family-owned working ranch. Dark sky certified. Amazing view of the Milky Way and stars. Scenic meadows, managed forest lands, and rock vistas make up the landscape. Enjoy the slow-paced country lifestyle in an authentic ranch setting with horses, cows and dogs. Guests are welcomed and encouraged to enjoy the whole property. Many hiking areas and views to explore. Usual snowy winters make great fun for cc skiing and snow shoeing.

Guest favorite

Home in Redmond

4.83 out of 5 average rating, 577 reviews

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

Guest favorite

Rental unit in Bend

4.95 out of 5 average rating, 1,166 reviews

Private apt, 1bdrm/1bath, with kitchen, in town

Brand new remodeled apt January 2024! 1 king bdrm/bath with living/dining/full kitchen apartment. Private entrance. 3 bright, light & spacious rooms, with treetop views. Kitchen has new full-size induction range and refrigerator, plus all cooking essentials. All new flooring/furnishings. Deck. In town location. Walking distance to NW Crossing, Newport Market, Galveston, also downtown Bend. Cycling routes just outside, 20 minutes to winter sports. NOTE-28 steps up from street! NO pets allowed!

Guest favorite

Home in Redmond

4.87 out of 5 average rating, 394 reviews

The Little Red Chimney House - 3 BR 2 BA

Originally built in 1944, this is a wonderfully furnished bungalow with 3 queen bedrooms and 2 full bathrooms, which I completely renovated and remodeled. It is a stone's throw from Fred Meyers grocery store and Cascade Lakes Brewery, and within easy walking distance to downtown. This house is at the hub of Central Oregon and sits at the crossroads between Bend (14 miles), Prineville (20 miles), and Sisters (20 miles) and is 10 miles from Smith Rock and 2 miles from the Airport.

Guest favorite

Rental unit in Bend

4.94 out of 5 average rating, 843 reviews

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

This 600+ square feet whimsical apartment is located in one of Bend's best neighborhoods, River West--only a 14-minute walk to downtown (.6 miles). The location’s also close to the river, Drake Park as well as many restaurants, cafes & galleries. It is perfect for couples or individuals looking for a cozy, retreat atmosphere in a lodge. The Garden Apartment has many amenities including free parking, AC, large clawfoot tub, washer/dryer, gas fireplace, HBO, cable and coffee.

Guest favorite

Home in Terrebonne

4.96 out of 5 average rating, 431 reviews

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to mine and I live on site with my daughters family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering or checking the NEW spa. We are open for a 2 night minimum. Checkout time is strict to allow for cleaning and sanitizing.