Family-friendly vacation rentals in Sisters

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Top-rated family-friendly rentals in Sisters

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Guest favorite

Guesthouse in Bend

4.98 out of 5 average rating, 503 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.

Jan 14 – 21

G$26,167 GYD per night

Guest favorite

Apartment in Redmond

4.97 out of 5 average rating, 431 reviews

Smith Rock View 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.

Nov 10 – 17

G$28,838 GYD per night

Guest favorite

Home in Bend

4.94 out of 5 average rating, 239 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.

Sep 9 – 16

G$30,009 GYD per night

Guest favorite

Guest suite in Bend

4.9 out of 5 average rating, 289 reviews

Cozy Studio! Walk to NW Crossing and Shevlin Park

Cozy, soft decor fill this light, bright studio with a private entrance. Shevlin Park and Phil's Trail are minutes away for hiking, running, and mountain biking. Mt. Bachelor is a short 30 minute drive for skiing in the winter and downhill biking in the summer. Smith Rock is a 45 minute drive for hiking and climbing enthusiasts. Shopping and dining are within walking distance at NW Crossing or a a short drive to the Old Mill or Downtown Bend. Mesh Network Wifi, coffee, tea and snacks provided.

Aug 29 – Sep 5

G$22,228 GYD per night

Guest favorite

Apartment in Sisters

4.94 out of 5 average rating, 145 reviews

Contemporary apartment in Sisters, OR. USA

A contemporary 2 bedroom apartment in a quiet neighborhood just 4 blocks from Sisters main street. Minutes from music venues, festival locations, trails, and popular biking routes. Sisters has art, music, movie theater, good coffee, beer, restaurants, and boutique shopping. Village Green is close by. Superb biking, hiking, skiing, fly fishing, and outdoor opportunities abound year round. The apartment is perfect for couples, solo adventurers, business travelers, and families.

Aug 28 – Sep 4

G$34,115 GYD per night

Guest favorite

Apartment in Bend

4.94 out of 5 average rating, 794 reviews

The Garden Apt-Hot Tub AC Fireplace 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.

Oct 11 – 18

G$19,227 GYD per night

Guest favorite

Guest suite in Bend

4.96 out of 5 average rating, 179 reviews

A little bit of Aloha in Central Oregon

Our home is located in NW Bend, central to downtown Bend, Sisters, and Redmond. We have a newly remodeled, attached 1 bedroom apartment suite. Privacy, comfort, and a bit of Hawaii aloha is yours here. The quality is equal to the finest hotels in Bend, but we're significantly more affordable and private! Perfect for a couple, two single adults, or a couple with one child. We are excited to share Bend and our home with you! 8 minute drive to downtown Bend. DCCA#1532

May 11 – 18

G$25,321 GYD per night

Guest favorite

Guesthouse in Bend

4.98 out of 5 average rating, 254 reviews

Country Apartment, Tumalo 2BR

Welcome to our spacious upstairs 2-bedroom studio apartment conveniently located 20 minutes from Bend, Sisters, and Redmond on Bend's scenic rural bicycle route, just minutes from the quaint little town of Tumalo. We are 20 minutes from Deschutes county fairground and 20 minutes from Hayden Homes Amphitheater. To really enjoy your country experience we welcome you to walk through the barn and check in with the family while you are here about petting the horses.

Jun 1 – 6

G$24,408 GYD per night

Guest favorite

Tiny home in Redmond

4.97 out of 5 average rating, 422 reviews

Timmys Tiny House 1

Tim's Tiny House This Comfy Tiny Home is "Business Ready" with 5G Wi-Fi & computer table. Private & secure parking w/lights. Centrally located, 15 minutes to Bend and Famous Smith Rocks, 20 min. to Prineville, 25 min. to Sisters. Also, 8 minutes to the Deschutes County Fair grounds and Municipal Airport. Also, several drinks in fridge all complementary. We follow all Airbnb's cleaning protocol.

Aug 26 – Sep 2

G$22,829 GYD per night

Guest favorite

Guest suite in Bend

4.93 out of 5 average rating, 657 reviews

Orchard District Studio

A cozy studio apartment; this converted garage space has tall ceilings making it feel light and airy. Located in Bend's Orchard District, it is walking distance to Hollinshead Park & Pilot Butte. We are NOT within walking distance to downtown, however it is only a 5 minute drive to downtown & 15 minutes to outdoor recreation opportunities. Hosts live in the main house. LGBQT+ BIPOC friendly.

Sep 16 – 23

G$17,242 GYD per night

Guest favorite

Guesthouse in Bend

4.95 out of 5 average rating, 291 reviews

Cabin on quiet 3 acres 10 min to downtown Bend.

Enjoy the peaceful serenity of our guest house. Enjoy a large lawn, irrigation pond with deck for hanging out, and a firepit. Our home is 10 minutes drive to downtown Bend; 45 minutes to Mt Bachelor; 40 minutes to Smith Rock; 20 minutes to Phil's trailhead for mountain biking (All times are without rush hour traffic). Come enjoy all that Bend has to offer!

Sep 13 – 20

G$19,122 GYD per night

Guest favorite

Guesthouse in Sisters

4.9 out of 5 average rating, 208 reviews

Sisters Casita Cottage

My place is close to the city center, parks, and all of beautiful Sisters! You’ll love the Cottage because of the location, the coziness and comfortable bed, the convenience and accessibility to the park and shops in town. The Cottage is good for couples and with an infant or small child, solo adventurers, and business travelers.

Oct 28 – Nov 4

G$32,178 GYD per night