Family-friendly holiday rentals in Sisters

4.99 out of 5 average rating, 154 reviews

A spacious living area features a sectional sofa in neutral tones, accompanied by a soft area rug. A stone fireplace adds warmth, while large glass doors open to a private balcony with outdoor seating. Natural light fills the room, enhancing the inviting ambiance.

Condo in Sisters

Beautiful Sisters Condo - Great location

Great location! Remodeled 2 bedroom and 2 bath condo is a spacious retreat set within the pine trees. The complex includes a seasonal pool. The hot tub/sauna are open year round. The club house includes ping pong, foosball and a pool table. You just need to walk through the city park and across the creek to get into town. We are also located about two blocks from the MovieHouse and Three Creeks Brewing. Enjoy bike paths close by and lots of hiking in the area. Easy self check-in and out.

KitchenFamilyParking

A spacious outdoor deck is furnished with a table and several comfortable chairs, providing an inviting space for gatherings. An umbrella offers shade, while a grill is positioned nearby. The surrounding trees create a natural backdrop, enhancing the tranquility of the setting.

4.85 out of 5 average rating, 100 reviews

Perfect Home in the Pines with hot tub!

Relax with family and friends in this peaceful Sisters home. Cozy and open the home has a smart TV along with stainless steel appliances, classic decor, and a great outdoor area in the back with a fire pit, BBQ and furniture. Only a couple minutes to downtown Sisters and 15 mins to ski at Hoodo. Free pool access at the Tollgate seasonal pool, pickle ball courts, a tennis court, basketball court, children's playground and many acres of National Forest land for miles of mountain biking or hiking.

FamilyIndoor spacesPool

4.98 out of 5 average rating, 980 reviews

The lookout tower is framed by green trees, featuring multiple wooden decks and a spacious entryway. Steps lead up to the main entrance, and large windows provide glimpses of the interior overlooking the natural landscape.

Home in Terrebonne

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!

FamilyKitchenCheckout

4.95 out of 5 average rating, 129 reviews

The cabin is nestled among tall pine trees in a serene wooded setting. A two-car garage stands adjacent to the cabin, with ample outdoor space featuring a carpet of mossy ground cover. Sunlight filters through the trees, creating a peaceful ambiance.

Cabin in Sisters

Serene family cabin in Sisters, Oregon.

Peaceful, well appointed spacious cabin in a Dark Sky community that embodies the spirit of central Oregon. The cabin is located 3 miles from Downtown Sisters, 20 minutes to Hoodoo & 10 minutes to Black Butte Ranch. We've geared the spaces towards fun and relaxation. Well curated amenities will help your family enjoy all that the Sisters area has to offer. From an easy to use propane fireplace to a fenced backyard for your pup, fully stocked kitchen, comfy beds and kid friendly amenities!

Indoor spacesKitchenSkiing

4.97 out of 5 average rating, 393 reviews

A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.

Home in Terrebonne

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

FamilyIndoor spacesBathroom

4.97 out of 5 average rating, 178 reviews

The cabin features a welcoming entrance with a wood deck and rustic details. Framed by green trees, the two-story structure showcases a steep gabled roof and large windows, providing a warm and inviting sight. A path leads to the entrance, surrounded by low shrubs.

Cabin in Sisters

Pet + kid friendly w/ private hot tub!

Relax with the whole family at this peaceful cabin in Sisters! Take a short drive into downtown Sisters or ride bikes into town via neighborhood trails to do some shopping or explore the nearby lakes, rivers and mountains. Or stay in! Enjoy happy hour on the roof top deck, unwind in the steamy hot tub, cook dinner in the fully equipped kitchen, or have a BBQ on the outdoor patio! This is the perfect place to experience all Sisters has to offer! Just the getaway you've been waiting for!

FamilyIndoor spacesOutdoor spaces

4.93 out of 5 average rating, 150 reviews

Modern Tollgate Home - HOT TUB | Half Acre Lot

This newly renovated 3 bedroom/2 bathroom home sits on more than a half acre lot in the quaint town of Sisters. When you stay at this Tollgate home you get all of the community amenities with it: community pool, pickle-ball/tennis courts, walking trails, basketball courts, etc. Bring the whole family as we comfortably sleep 6 people and enjoy the hot tub! This is an incredibly well-done high-end modern home that is virtually brand new. We are also a dog friendly home ($100/stay fee).

FamilyKitchenCheckout

4.9 out of 5 average rating, 295 reviews

A studio cabin is positioned on a deck overlooking a canyon, surrounded by native plants. Two wooden chairs are placed on the deck, providing a space to absorb the expansive mountain views in the distance. The structure features a large window reflecting the evening light.

Cabin in Culver

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

Indoor spacesFamilyParks

4.95 out of 5 average rating, 192 reviews

A comfortable living area features a bright red sofa and an additional lounge chair. Natural light filters through large windows, highlighting the neutral wall colors and carpeting. A television is positioned on a sturdy stand, while a small dining table is visible in a corner.

Apartment in Sisters

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.

KitchenIndoor spacesAir conditioning

4.87 out of 5 average rating, 436 reviews

A cozy living area is seen, featuring a dark sofa against the wall, a coffee table, and a flat-screen TV mounted nearby. The kitchenette includes dark cabinetry, a microwave, and a mini fridge. A clock on the wall and ample natural light enhance the space.

Townhouse in Sisters

Walk to Town Family Meeting Place AIRBNBOB

Home built in 2017 with AirBnb in mind. Private entrance. Smart lock access to upstairs flat. Master bedroom with king bed. Balcony bedroom with amazing queen electric bed (New). Trundle couch with two single beds. Electric cooking area. Mini fridge. Balcony view of snowcapped mountains. High speed WIFI. Wide Screen TV. Apple TV access to Netflix, Youtube, Amazon Prime, etc. New Bidet installed in April 2019.

Indoor spacesKitchenCheckout

4.98 out of 5 average rating, 209 reviews

A charming cottage exterior is depicted, featuring a white picket fence and a welcoming covered porch. Lush green grass surrounds the house, complemented by tall trees in the background. A hanging plant basket adds a touch of greenery, enhancing the inviting entrance.

Cottage in Sisters

Minutes walk Downtown/Cozy Cottage Retreat/Sauna.

“Escape to a special place I call my cottage, a peaceful sanctuary just steps from downtown. Nestled among tall Ponderosa pines with Whychus Creek flowing nearby, for a quick cold plunge. Enjoy a lush private backyard perfect for stargazing from the hammock under the night sky. Multiple decks, a covered gazebo with warm ambient lighting, and a private sauna await you.”

Indoor spacesKitchenOutdoor spaces

A comfortable living area is highlighted by a large sectional couch adorned with soft pillows. A wood stove provides warmth, while multiple windows offer views of the surrounding Ponderosa Pine forest. A coffee table holds a decorative tray, contributing to the cozy ambiance.

4.94 out of 5 average rating, 269 reviews

Private Peaceful Cabin in Sisters!

Upon your arrival in Tollgate, a wonderful community only 1.5 miles out of Sisters, you will feel the stresses of your everyday life magically drop away as you are surrounded by the serenity and beauty of a Ponderosa Pine forest within the quiet ambiance of Tollgate.

FamilyIndoor spacesRiver

Popular amenities for Sisters family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 167 reviews

The exterior of the Cozy Hideaway features a red cabin with a covered deck supported by wooden beams. A hammock is seen on the deck beside a hot tub, surrounded by a natural landscape of pines and grassy areas.

Cabin in Sisters

Cozy Hideaway w/outdoor living and hot tub!

FamilyIndoor spacesLocation

The front exterior of the newly constructed home features a welcoming entrance with large glass doors framed by warm lighting. A landscaped pathway of stones leads to the entrance, surrounded by gravel and desert flora, under a colorful twilight sky.

4.95 out of 5 average rating, 155 reviews

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

Indoor spacesKitchenAir conditioning

4.94 out of 5 average rating, 268 reviews

An A-frame cabin is set against a colorful sunset, showcasing warm lights illuminating the exterior. The front entrance features a door with a welcoming window, while two rustic chairs sit on the porch, accompanied by potted plants and neatly stacked firewood.

Cabin in Bend

Black Duck Cabin

Indoor spacesFamilySolo travel

4.98 out of 5 average rating, 284 reviews

The exterior of the chalet is showcased, featuring a peaked roof and large windows that allow ample natural light. A spacious wooden deck is present, accompanied by outdoor seating and a barbecue. The surrounding grassy area enhances the outdoor setting.

Chalet in Redmond

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!

Indoor spacesKitchenAccuracy

A modern living room is highlighted by a large flat-screen TV and a stylish fireplace. Expansive windows provide views of the outdoors, allowing natural light to fill the space. Comfortable seating arrangements create an inviting area for relaxation.

4.99 out of 5 average rating, 139 reviews

Cozy Mountain Escape: Amazing Views! Hot tub!

Indoor spacesKitchenBathroom

4.9 out of 5 average rating, 230 reviews

A welcoming living area features a gas fireplace set within a brick surround. Large windows provide natural light and views of the outdoor space. A comfortable seating arrangement includes a dark sofa and a coffee table, while a bookshelf is filled with various books.

Townhouse in Sisters

Sisters Getaway

Indoor spacesKitchenQuiet

4.9 out of 5 average rating, 331 reviews

An A-frame interior features warm wooden paneling, with a cozy seating area highlighted by a stylish armchair and a television unit. The open door reveals a view of the outdoor pathway, surrounded by greenery, bringing natural light into the space.

Tiny home in Bend

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

FamilyKitchenAccess

The exterior of a spacious home is shown, featuring a light brown facade and large windows that provide ample natural light. A wooden deck is visible at the front, furnished with several outdoor chairs, and surrounded by tall, green trees in a serene landscape.

4.93 out of 5 average rating, 137 reviews

Black Butte Ranch Family Friendly Home Sleeps 14

Indoor spacesKitchenDecor

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 298 reviews

Guest suite in La Pine

Guest suite | Hot tub & sauna Cabin in the Woods

KitchenIndoor spacesWalkability

4.88 out of 5 average rating, 123 reviews

The exterior of the newly built condo is showcased, featuring a well-maintained landscape with colorful shrubs and flowers. Paved walkways lead to the entrance, framed by trees. The modern architecture includes a combination of stone and wood accents, enhancing the inviting curb appeal.

Condo in Sisters

Views! 1 Blk to Town, Clean+Charming,pets ok-North

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 240 reviews

Butler Corner - New, Clean & Minutes From Downtown

KitchenFamilyHeating

The cozy bedroom features a rustic wooden bed frame with soft linens, complemented by natural light from a nearby window. A stylish soaking tub is presented with a wooden shelf nearby. The kitchen showcases modern appliances with a striking blue cabinetry, while a snowy mountain landscape is displayed outdoors.

4.95 out of 5 average rating, 319 reviews

Romantic Farmhouse near Mt. Bachelor

KitchenFamilyView

4.85 out of 5 average rating, 291 reviews

A colorful hammock is suspended from a snow-covered tree, inviting relaxation. The quaint WeeHouse, featuring large windows and a bright yellow door, is partly obscured by the snow. A serene winter landscape surrounds the property, showcasing the tranquility of the setting.

Tiny home in Bend

IT'S A WEE HOUSE

Indoor spacesKitchenWalkability

A wooden deck overlooks a serene river, flanked by lush greenery. Two comfortable armchairs with bright cushions are arranged around a small table, inviting relaxation and enjoyment of the peaceful environment.

4.84 out of 5 average rating, 475 reviews

River View Inn a cabin on the River

FamilyKitchenGetting around

5 out of 5 average rating, 171 reviews

An inviting hot tub is positioned alongside a sauna grotto, both nestled within a natural setting. The hot tub features clear water with soft illumination, while the sauna's wooden exterior is accentuated by warm light. Surrounding trees and rocks enhance the tranquil atmosphere.

Bungalow in Bend

River Run Bend Bungalow & Romantic Spa Grotto

FamilyIndoor spacesAccess

4.97 out of 5 average rating, 518 reviews

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

Home in Terrebonne

Canyon House, Crooked River Ranch

FamilyIndoor spacesLayout

Family-friendly home rentals with a pool

The exterior of a large two-story house is displayed, featuring a covered porch supported by columns. Lush green grass surrounds the structure, complemented by neatly arranged shrubs. A clear blue sky with soft clouds is visible above, enhancing the overall setting.

4.93 out of 5 average rating, 284 reviews

Updated Game Room! Hot Tub, SHARC (8), 2,800sq/ft

KitchenIndoor spacesView

4.92 out of 5 average rating, 178 reviews

The living area features vaulted wooden ceilings and large windows that allow ample natural light. A stone fireplace is situated beside two dark leather sofas, facing a wooden coffee table. A dining table with chairs is visible in the background, creating a welcoming space.

Chalet in Redmond

3bdrm Chalet + Hot Tub in Eagle Crest

Indoor spacesFamilyHospitality

4.95 out of 5 average rating, 138 reviews

The open living area features two brown leather couches and a large coffee table set on a patterned rug. A flat-screen TV sits on a white media console. Bright natural light enters through multiple windows, creating a welcoming atmosphere that connects to the dining area.

Condo in Sisters

Renovated Sisters Condo; perfect getaway!

KitchenFamilyCheck-in

The exterior of a charming townhome is presented, featuring a blend of textured siding and stone accents. A covered porch with wooden railing invites relaxation, while landscaped greenery and a stone pathway enhance the entrance. Large windows allow natural light to illuminate the space.

5 out of 5 average rating, 43 reviews

Beautiful Townhome with Patio

Indoor spacesKitchenWalkability

4.99 out of 5 average rating, 218 reviews

An aerial view captures the expansive property featuring a lush English Country Garden filled with vibrant flowers and greenery. A serene swimming pond is visible in the foreground, while the well-maintained guest suite is framed by trees in the background.

Guest suite in Bend

Luxurious Private Tumalo Suite Nestled in Trees

Indoor spacesKitchenBathroom

4.96 out of 5 average rating, 138 reviews

An open living area is displayed, featuring a dark leather sofa and a wooden coffee table. A dining area with wooden chairs is seen in the background, along with a well-equipped kitchen that is partially visible. Natural light brightens the space, highlighting the warm wood flooring.

Townhouse in Redmond

Eagle Crest townhome Dog friendly-sleeps up to 6

Indoor spacesFamilyQuiet

5 out of 5 average rating, 8 reviews

Meadows' Edge at Black Butte Ranch

FamilyAmenitiesLocation

A cozy living space features a comfortable gray sofa with decorative pillows, a wooden coffee table, and a dining area with a table and chairs. Natural light fills the room through tall windows, illuminating the rustic wooden accents and equipped kitchen in the background.