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Cottage vacation rentals in Sisters

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Quick stats about cottage rentals in Sisters

  • Nightly prices starting at

    Sisters vacation rentals start at $312 CAD per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Sisters rentals

  • 5 Average rating

    Sisters stays are highly rated by guests—averaging 5 out of 5!

Top-rated cottage rentals in Sisters

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favourite
An outdoor living space features four wooden Adirondack chairs arranged around a smokeless firepit. A hot tub and sauna are visible within a nearby structure, with steam rising gently from the hot tub. The area is surrounded by a wooden fence and trees.
Cottage in Old Bend

Historic Old Bend Cottage & Carriage House Spa

This historic Old Town Bend cottage boasts a relaxing setting for unwinding with a lovely cedar hot tub & sauna in its restored carriage house. Walk to the attractions: 0.2 mi. to the best shops and restaurants, and 0.4 mi. to Mirror Pond & Drake Park! Split heating in each room, snow gear storage in the laundry room, grill, and new washer/dryer. Driveway and extra street parking (free). Fast WiFi and a smart TV. Fully stocked kitchen and bathroom so you and your fur babies can come and unwind!

LocationValueQuiet

4.98 out of 5 average rating, 186 reviews
Guest favourite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne

Quiet central Oregon desert retreat with a view!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

ValueFamilyCheck-in

4.9 out of 5 average rating, 349 reviews
Top guest favourite
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.
Cottage in Bend

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

ValueFamilyAir conditioning

4.91 out of 5 average rating, 385 reviews
Top guest favourite
A modern kitchen is equipped with wooden cabinetry, stainless steel appliances, and a decorative counter space. The kitchen features a gas oven and microwave, alongside a coffee maker. Natural light enters through a nearby window with wooden blinds, and a vase of colorful flowers adds a cheerful touch.
Cottage in Bend

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ . Garage is secure and available UPON REQUEST. Lastly, wireless internet is smokin, 1gb. Early check in available $10hr

FamilyLocationGetting around

4.99 out of 5 average rating, 160 reviews
Guest favourite
An open living area is illuminated by natural light, featuring large windows that provide views of the outdoor landscape. A wooden dining table is placed beside a seating area, which includes a dark green sofa. Distinctive lighting fixtures and wooden beams add character to the space.
Cottage in Bend

New mid century cottage w/ Mountain View

Welcome to Central Oregon! Tumalo is a quaint farming community 15 minutes from Bend, Redmond, and Sisters. It's the most central location to incredible rivers, climbing, hiking, skiing, biking, and all other activities you enjoy. The exterior is in a constant state of improvement! Depending on when you come, you may see piles of dirt and rock, or new vegetation, mulch. Update...the inside space has a nice new leather couch. I am NOT advertising a hot tub because it’s not working yet!

FamilyLocationSleep quality

4.8 out of 5 average rating, 142 reviews
Top guest favourite
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. Indulge in a quick, invigorating cold plunge. Enjoy a tranquil private backyard for privacy and grounding. Perfect for stargazing from the hammock under the night sky. Multiple decks with seating, a covered gazebo with warm ambient lights, and finally a private sauna await you.” An amazing way to relax, de-stress, and unwind!

FamilyValueParking

4.98 out of 5 average rating, 218 reviews
Top guest favourite
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!

ValueFamilyGetting around

4.98 out of 5 average rating, 160 reviews
Top guest favourite
Cottage in Bend

Galveston Getaway to all the fun in Bend Oregon

Galveston Getaway is an original 1919 Bend cottage that has been updated and remodeled while retaining the original charm. The cottage is stylish but comfortably furnished, and in the perfect location on the west side. Guests will be able to walk to restaurants, shopping, brew pubs, and Drake Park. Mountain bike trails are within riding distance to the house. Mt. Bachelor with all of its activities is only a short drive. The house is fully equipped to a make your Bend stay perfect.

FamilyValueLong stay

4.97 out of 5 average rating, 189 reviews
Guest favourite
A cozy seating area is presented with a gray armchair beside a small white dining table. A decorative mirror and greenery adorn the wall, while sunlight filters through a nearby window, illuminating the space. A rug adds warmth to the wooden floor.
Cottage in Redmond

Blossom Cottage Studio

Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

FamilyValueHiking

4.92 out of 5 average rating, 187 reviews
Guest favourite
A modern kitchen features sleek cabinetry and quartz countertops, complemented by stainless steel appliances. Two wooden stools sit at the kitchen island, with a spacious layout that encourages cooking and socializing.
Cottage in Old Bend

Contemporary Chic, Walk Downtown, Gourmet Kitchen

Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage embodies the spirit of Bend. This charming two bedroom, one bathroom vacation home is ideal for those Bend explorers who wish to be in the heart of it all. This house is located on a vibrant and eclectic street, situated just two blocks from downtown Bend. You are just a short stroll to all the superb dining, infamous breweries, art galleries, and festivals.

FamilyValueGrill

4.95 out of 5 average rating, 327 reviews
Top guest favourite
The exterior of the cottage features a charming pink facade complemented by white trim. Baskets with flowers hang from the eaves, and a decorative sign is centered above the front door, enhancing the welcoming entrance.
Cottage in Bend

Vintage Pink Walk to town Hot Tub

Our 106 year-old lovingly restored 1920 cottage is 3 blocks from First Street River Rapids, 25 minutes to Bachelor & 10 minute walk to Town. Centrally located urban setting on a main street. Step back in time, the original charm was painstakingly preserved, with original claw foot with shower and bathtub (which requires adequate mobility) and wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.

FamilyLocationSleep quality

4.95 out of 5 average rating, 501 reviews
Top guest favourite
A welcoming front porch features two white folding chairs and a small table. Potted flowers add color to the space. The green door complements the light exterior, while overhead lights enhance visibility. Natural light filters through the surrounding trees.
Cottage in Bend

Adorable West Side Cottage, Pet Friendly!

Enjoy a cozy and comfortable stay in my 1-bedroom, 2-bathroom home, complete with a bonus room that offers plenty of privacy when needed and a plush futon that allows for two additional guests (best for up to 3 adults or 2 adults and 2 kids, or two couples would work as a well ) Conveniently located within walking distance of Newport Market, Backporch Coffee, Chow, and Spork, it's just five blocks from downtown

LocationFamilyPets

4.95 out of 5 average rating, 405 reviews

Popular amenities for Sisters cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favourite
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

LocationValueBathroom

5.0 out of 5 average rating, 56 reviews
Guest favourite
A charming cottage exterior is presented, featuring a welcoming front porch with red chairs and decorative throw pillows. Flower beds, filled with white and purple blooms, line the path leading to the entrance. Three vertically positioned windows above the door allow natural light to enhance the facade.
Cottage in Sisters

Cozy Sisters Cottage | Pool • Walk to Town • Dogs

LocationValueWalkability

4.94 out of 5 average rating, 83 reviews
Superhost
A cozy living area is highlighted by large windows allowing ample natural light. A dark sofa adorned with decorative pillows faces a wooden coffee table. A wall-mounted television and art pieces complement the space, while a dining area with chairs is visible in the background.
Cottage in Redmond

Come Stay and Play at Little Les Cheneaux Retreat

ValueLocationHospitality

4.87 out of 5 average rating, 77 reviews
Guest favourite
A cozy home is nestled among tall trees, featuring a spacious deck that wraps around the front. The structure is painted in a soft shade of yellow, highlighted by a chimney, and surrounded by natural landscaping and shrubs.
Cottage in Bend

Cloudchaser Cottage: Cozy Get-Away

LocationValueIndoor spaces

4.94 out of 5 average rating, 63 reviews
Guest favourite
A spacious patio area is presented with a large red umbrella over a dining set featuring four patterned chairs. A hot tub is positioned nearby, with a grill partially visible in the background. Surrounding greenery adds a touch of nature to the setting.
Cottage in Bend

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

LocationFamilyBiking

4.94 out of 5 average rating, 348 reviews
Guest favourite
A charming craftsman-style home is set amidst a lush green yard, with a well-defined pathway leading to the welcoming red front door. The porch is framed by well-maintained shrubbery, while trees provide a serene backdrop.
Cottage in Bend

One Block to Downtown, Hot Tub, Private Home, Yard

ValueLocationTV

4.93 out of 5 average rating, 200 reviews
Guest favourite
A charming cottage is set on a well-maintained lawn, showcasing a welcoming entryway with a wooden door and large front windows. The exterior features a combination of light green siding and rich brown accents, surrounded by trees and shrubs that enhance the inviting appearance.
Cottage in Old Bend

Historic Downtown, Private Hot Tub, High Demand

FamilyValueParking

4.93 out of 5 average rating, 275 reviewsA modern kitchen area is highlighted by a spacious island topped with fresh fruit, and sleek, dark cabinetry. Stylish pendant lights hang above, while a cozy seating area features a grey sectional sofa. A fireplace and wall art add warmth to the space.
Cottage in Bend

Popular cottage at Tetherow! Hot Tub + comfy beds

FamilyLocationAmenities

Pet-friendly cottage rentals

Guest favourite
The exterior of a blue cottage features a welcoming front porch with two chairs and a small table. Lush greenery surrounds the entrance, enhancing the inviting atmosphere. A pathway leads to the front steps, framed by decorative stones and natural landscaping.
Cottage in Old Bend

Historic Old Town Cottage, walkable Downtown Bend

LocationFamilyGetting around

4.88 out of 5 average rating, 473 reviews
Guest favourite
The exterior of the Greeley Cottage features a charming white facade with dark trim. Multiple windows offer natural light, while potted plants flank the entrance. A black front door is adorned with a decorative lamp, inviting guests into the home.
Cottage in Bend

Stylish Downtown Cottage, Walk Everywhere

FamilyLocationCheck-in

4.96 out of 5 average rating, 46 reviews
Guest favourite
A rustic building, styled like an old saloon, is set against a clear blue sky. The structure features wooden siding and a wide covered porch, surrounded by open grassy areas and various trees in the background. Historical signage completes the charming exterior.
Cottage in Bend

Dog-Friendly Ranch Cottage w/ Yard ~ 13 Mi to Bend

LocationFamilySleep quality

4.97 out of 5 average rating, 76 reviews
Top guest favourite
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.
Cottage in Bend

The Blackberry Cottage

ValueFamilyAir conditioning

4.91 out of 5 average rating, 385 reviews
Guest favourite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne

Quiet central Oregon desert retreat with a view!

ValueFamilyCheck-in

4.9 out of 5 average rating, 349 reviews
Top guest favourite
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

ValueFamilyGetting around

4.98 out of 5 average rating, 160 reviews
Top guest favourite
An outdoor living space features four wooden Adirondack chairs arranged around a smokeless firepit. A hot tub and sauna are visible within a nearby structure, with steam rising gently from the hot tub. The area is surrounded by a wooden fence and trees.
Cottage in Old Bend

Historic Old Bend Cottage & Carriage House Spa

LocationValueQuiet

4.98 out of 5 average rating, 186 reviews
Top guest favourite
Cottage in Bend

Galveston Getaway to all the fun in Bend Oregon

FamilyValueLong stay

4.97 out of 5 average rating, 189 reviews

Private cottage rentals

Guest favourite
A living room with hardwood floors features a decorative stone fireplace and a wall-mounted TV. Natural light enters through a window with light curtains. Seating includes a gray sofa, a wooden bench, and a coffee table atop a blue rug.
Cottage in Bend

Downtown, Modern Nostalgia--walk to shops, cafes

LocationFamilyLong stay

4.91 out of 5 average rating, 505 reviews
Top guest favourite
Cottage in La Pine

A Romantic Riverfront Cottage @ Wildlife Sanctuary

FamilyLocationCheck-in

4.98 out of 5 average rating, 51 reviews
Top guest favourite
Cottage in Bend

Upscale Downtown Cottage-Extended Stays welcome

LocationFamilyBiking

4.98 out of 5 average rating, 131 reviews
Top guest favourite
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.

FamilyValueParking

4.98 out of 5 average rating, 218 reviews
Top guest favourite
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.
Cottage in Bend

The Blackberry Cottage

ValueFamilyAir conditioning

4.91 out of 5 average rating, 385 reviews
Guest favourite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne

Quiet central Oregon desert retreat with a view!

ValueFamilyCheck-in

4.9 out of 5 average rating, 349 reviews
Top guest favourite
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

ValueFamilyGetting around

4.98 out of 5 average rating, 160 reviews
Top guest favourite
A charming exterior view of the rustic cabin showcases a covered porch with comfortable seating. Surrounding landscaping features a variety of plants and rocks, complemented by a small fire pit area. The home's muted color palette blends harmoniously with the natural setting.
Cottage in Bend

River Camp House

ValueFamilyWalkability

4.98 out of 5 average rating, 165 reviews

Destinations to explore