Pet-friendly holiday rentals in Sisters

4.94 out of 5 average rating, 123 reviews

Cozy family cabin in Sisters, Central Oregon.

Relax with the family at this peaceful well appointed spacious cabin 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!

4.98 out of 5 average rating, 951 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!

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.

4.97 out of 5 average rating, 258 reviews

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

5 out of 5 average rating, 127 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

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

4.99 out of 5 average rating, 137 reviews

The exterior of a renovated farmhouse showcases a wooden fence enclosing a gravel area, with a welcoming entrance. Two outdoor chairs are positioned near the entry, and a BBQ grill is visible, indicating a space for outdoor cooking and relaxation.

Cottage in Bend

The Tumalo House

The Tumalo House is located just north of Bend and is situated between Tumalo Cider and Bend Cider. Just across the street from The Bite, the local hang out, this fully renovated 1940's farm house offers 2 bedrooms, sofa bed and 1 bath, and outdoor space with a gas fire pit. This cozy find is only steps from the Deschutes river, 30 minutes from Mt. Bachelor and minutes from Downtown Bend and The Shops at the Old Mill. No matter what brings you here, this home will make you want to stay!

4.97 out of 5 average rating, 102 reviews

Downtown Pine Mountain Paradise

Classic Pine Meadow Paradise! 3 bedrooms and an additional ADU, this consists of one King bed, two Queen beds and two twin beds. You will love all of the natural light and french doors right off the living room. Fully equipped kitchen with Island. Master bedroom has mountain views, sandstone shower and soaking tub upstairs. There is also a private ADU over the garage guests are free to use. Enjoy sitting around on the wrap around porch with your favorite drink with family and friends.

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.

4.96 out of 5 average rating, 154 reviews

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!

4.93 out of 5 average rating, 133 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).

4.89 out of 5 average rating, 246 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.

4.97 out of 5 average rating, 497 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

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 ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

4.92 out of 5 average rating, 141 reviews

The exterior of the condo features a welcoming entrance, framed by vibrant landscaping. A covered porch with seating is visible, alongside manicured shrubs and decorative plants. Bright sunlight highlights the facade, creating an inviting atmosphere.

Apartment in Sisters

Views! 1 Blk to Town,New+Spotless, pets ok- South

Prime safe Sister's upscale neighborhood! Newly built condo offers EVERYTHING you expect without sacrificing a thing! Perfect INTERNET/WI-Fi and ONLY 1 BLOCK to downtown, restaurants, shopping. Leave your car at the unit and walk! Nice kitchen, king size bed in master, new queen size sofa/sleeper in living room! Relax on sofa or recliner w/ EXCELLENT Wi-FI, internet, cable, Netflix. Washer and dryer too! $35.00 pet fee PER pet under 40 lbs for the stay, Limit 2 pets.

A charming single-story home is surrounded by lush greenery and old growth ponderosa pines. The entryway features a winding path leading to the front door, with well-maintained landscaping including planted grasses and rocks.

4.96 out of 5 average rating, 178 reviews

Cozy Cottage | Hot Tub | Pet Friendly | Fenced

Get ready to enjoy all that the beautiful town of Sisters has to offer from this tasteful retreat. Here you will find yourself in a quiet neighborhood surrounded by majestic old growth ponderosa pines. Relax and enjoy the tasteful craftsmanship of the home and walk to Sisters for an evening on the town. Finish the day right with a soak in the hot tub! The side yard fence is perfect for your furry friends. Before you leave you’ll be planning your return trip!

Popular amenities for Sisters pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 116 reviews

Two blue Adirondack chairs are positioned on a lush green lawn, overlooking the calm Little Deschutes River. In the background, the river reflects the surrounding trees and grassy areas under a clear sky, creating a serene outdoor space for relaxation.

Home in La Pine

Riverfront/Hot Tub/Dock/Pet Friendly/Game Room

An open living space is displayed, featuring sliding barn doors that lead to a bedroom. A large wall artwork of a bridge over a misty landscape adds depth, while a cozy armchair and a small ornate table create inviting seating options.

4.88 out of 5 average rating, 428 reviews

Charming east side house, with hot tub.

4.86 out of 5 average rating, 204 reviews

A spacious dining area is accented by large windows that allow natural light to fill the space. A modern black table with vibrant orange chairs creates a striking visual contrast against the warm wooden interior. A spiral staircase is visible in the foreground.

Home in Sunriver

Stylish Modern A-Frame, steps to Village

4.98 out of 5 average rating, 313 reviews

Home in Orchard District

Have a Patio Barbecue at a Pet-Friendly House in Midtown

A modern home is surrounded by snow-covered trees, showcasing large windows that reflect natural light. The wooden exterior complements the winter landscape, while steps lead from the porch to the yard blanketed in fresh snow.

4.92 out of 5 average rating, 133 reviews

Black Butte Ranch Home with THE View

Home in Black Butte Ranch

4.74 out of 5 average rating, 113 reviews

Hot tub. Golf. Wood fireplace. Resort Access.

Home in Old Farm District

4.97 out of 5 average rating, 171 reviews

Bend Mid-Century Getaway• Near Old Mill & Downtown

Home in Old Farm District

A serene view of the Central Oregon Historic Canal features calm waters reflecting blue skies. Lush greenery and wildflowers border the waterway, creating a peaceful natural environment surrounded by trees. The landscape invites exploration along the trail for hiking or biking.

4.99 out of 5 average rating, 124 reviews

Dog-friendly | Hot tub | Close to everything

Pet-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.

4.92 out of 5 average rating, 273 reviews

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

Cabin in Crooked River Ranch

A row of rustic cabins is set against a natural backdrop, showcasing wooden exteriors and inviting porches. Each cabin features a distinct entrance, with picnic tables arranged on the deck. A gravel path leads through the surrounding shrubbery, offering a sense of tranquility.

4.93 out of 5 average rating, 126 reviews

Classic Cozy Cabin with Awe-inspiring Views

4.96 out of 5 average rating, 120 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

4.94 out of 5 average rating, 109 reviews

Townhouse in Redmond

Creekside Escape at Eagle Crest Golf Resort

4.88 out of 5 average rating, 289 reviews

A shaded deck area features a striped umbrella over a black dining table with four chairs. A private hot tub is positioned to one side, and expansive views of green fairways and tall trees are visible in the background.

Townhouse in Redmond

Eagle Crest-w/private hot tub/Resort passes!

4.97 out of 5 average rating, 178 reviews

An indoor pool room features a heated dipping pool, surrounded by vibrant red lounge chairs. A seating area is present with a couch and decorative pillows, while bright artwork adorns the walls. Sliding glass doors allow natural light and lead to the outside.

Home in Larkspur

Heated Indoor Pool | Game room I Pets Welcome!

4.86 out of 5 average rating, 119 reviews

The exterior of the home displays a combination of dark blue siding and natural stone accents. A spacious front porch is featured, along with two garage doors and a wide paved driveway. The sloped roof adds to the home's structural interest.

Home in Redmond

Stunning mtn Views, sleeps 14, Hot tub, rec passes

4.92 out of 5 average rating, 139 reviews

Red Clover Cabin at Black Butte Ranch (+Hot Tub)

Private, pet-friendly home rentals

A-frame cabin is framed by tall pine trees, showcasing a spacious wooden deck with steps leading to an outdoor hot tub. Large windows allow natural light to fill the interior, while a shaded area offers seating under an umbrella.

4.97 out of 5 average rating, 76 reviews

Majestic A-Frame on 5 acres!

4.94 out of 5 average rating, 32 reviews

Bend-Tumalo Retreat | 2+ Acres | Fire Pit | Dogs

4.99 out of 5 average rating, 366 reviews

A private hot tub is nestled among sparse trees on a slight elevation, offering serene views of the surrounding landscape. The cottage's exterior, featuring large windows, is visible in the background, set against a backdrop of a clear sky and natural foliage.

Guest house in Bend

Ranch Cottage: Desert, Forest, Horses, Hot Tub

5 out of 5 average rating, 13 reviews

The exterior of the cabin features a two-story structure surrounded by tall trees. A spacious deck with string lights invites relaxation, while two light green chairs are positioned around a fire pit in the grassy yard, creating an ideal setting for outdoor gatherings.

Home in Camp Sherman

Camp Sherman Riverfront Getaway - sleeps 8!

Cottage in Orchard District

The exterior of the cottage is shown with a charming deck and two white chairs positioned under string lights. A well-maintained path leads through lush greenery and stone steps to the entrance, highlighting the inviting atmosphere of the cottage.

4.9 out of 5 average rating, 350 reviews

The Blackberry Cottage

5 out of 5 average rating, 40 reviews

An outdoor seating area is surrounded by snow-covered ground, featuring a rectangular fire pit at the center. Several chairs with cushions in various colors are arranged around it. The cottage's warm lights glow invitingly through large glass doors, framed by tall trees in the background.

Cottage in Sisters

Hot Tub, Fire Pit, Dog Friendly

5 out of 5 average rating, 36 reviews

An aerial view of a green cabin set against a sunset sky featuring mountains in the background. A spacious lawn surrounds the cabin, highlighted by a stone fire pit with seating and a small pond. Nearby, wooden fencing encloses a garden area.

Guest house in Bend

Cozy Cabin near Sisters

The single-story Rancher's House is framed by expansive greenery and a serene pond, with a backdrop of snow-capped Three Sisters mountains. Tall pine trees dot the landscape, enhancing the connection to nature and the rural setting.