Holiday rentals with a kayak in Black Butte Ranch

The living room features a stone fireplace surrounded by wooden shelves, with a large flat-screen TV mounted above. A rustic wooden coffee table sits on a patterned area rug, complemented by leather seating and large windows that allow natural light to flood the space.

4.96 out of 5 average rating, 133 reviews

Sunriver Luxury Family Home at Caldera Springs

Your next adventure begins here! Explore the limitless activities of Central Oregon from our luxurious home in Caldera Springs Resort at Sunriver located 14 miles South of Bend. Built for families and friends with three bedroom suites, upstairs loft bedroom with bunk beds & sofa bed, and flexible office with sofa bed. Features private hot tub, outdoor gas fire pit and BBQ, game room with ping pong/foosball/arcade, big screen TVs, Sonos, and more! Short walk to Caldera Springs pool and amenities.

4.98 out of 5 average rating, 164 reviews

A wooden dock extends over the clear waters of the Spring River, featuring a bright yellow kayak resting on the edge. A paddle lies nearby, and lush greenery surrounds the tranquil scene, providing a serene backdrop of trees and natural beauty.

Cabin in Sunriver

Riverfront Ski Cabin w/ HotTub & Dock

Riverfront cabin w/ fantastic location! Conveniently located to the Sunriver Village (5 min) & Mt. Bachelor (20 min). Take it easy @ this unique, round house perched over the Spring River w/ 2 levels of decking, hot tub & private dock! Enjoy snow activities, hiking & biking. Kayaks, SUP, canoe & bikes available during summer.Stunning 180 degree views of the river. House is well stocked w/ all the creature comforts. This home is truly a peaceful oasis for some fun and R&R! 1 dog limit, $100 fee.

5 out of 5 average rating, 122 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 and pillows, dedicated free parking (incl. extra cars or small RV), outdoor dining and patio area, washer/dryer, and kitchen fully stocked with everything you need for fun and relaxation for all seasons!

4.92 out of 5 average rating, 135 reviews

The exterior of a log cabin is showcased, featuring a spacious outdoor seating area with a fire pit. Comfortable lounge chairs and a dining space are positioned near a hot tub, with tall pines providing a natural backdrop. Warm lighting enhances the welcoming environment.

Cabin in Sunriver

On Deschutes River | Kayak | HotTub | EVCharger

Make some memories at @YourRiverfrontRetreat - a unique and family-friendly place . This cabin is located on the Deschutes river with a private dock and access - with provided kayaks, canoe, paddleboards and tubes. It is 30 minutes from Mount Bachelor and 8 min from the Sunriver resort, with tons of access to the outdoors. Enjoy your private hot tub and fire pit after a fun filled day. Enjoy the beautiful starry sky on a clear night. A perfect place to relax, spend time with family/friends, and/

The cabin's exterior is crafted with natural wood and features large, angular windows that showcase the surrounding forest. A spacious deck with Adirondack chairs extends across the front, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 168 reviews

Private Luxury w/Hot Tub on Pvt Lake Amazing Views

The private & spectacular Lakeside West Cabin (3 bedr/3.5 bath, sleeps 8) overlooks Tumalo Lake with cozy wood-burning stove, private hot tub, & amazing lake views. 12 mi to downtown Bend, 45 min to Mt Bachelor and 4 mi to Tumalo Falls. Immerse in nature and be as active as you choose: hiking, mountain biking, fishing, complimentary canoes, kayaks, SUPs, snowshoeing, sledding, hammock, horseshoe and corn hole game, shared fire pit. Need more or less space? We have 2, 4 and 6 - 8 bedroom cabins.

4.93 out of 5 average rating, 296 reviews

A cozy bedroom features a log bed with decorative pillows, complemented by a ceiling fan. Natural light filters through a large window, illuminating warm wooden flooring. An accent lamp and a small plant are placed beside the bed, adding subtle elements of design.

Guest suite in Bend

Cozy Queen, Private Bathroom and Entryway

Peaceful, intimate bedroom (referred to as a “studio”) with a generously sized bathroom. Facing a large, sunny community space, enjoy amenities like a Keurig, heated bathroom floors, log bed, AC and PRIVACY. Experience a quaint, welcoming atmosphere, making it effortless for you to focus on what truly matters—creating cherished memories during your stay. This studio features WiFi, washer/dryer, kitchen essentials, TV with streaming, EV charger and self-check in. The studio is 300 square feet.

4.94 out of 5 average rating, 137 reviews

A spacious backyard is shown, featuring a well-manicured lawn and a shaded seating area. The modern chalet is visible in the background, with large windows and a stone chimney. A hot tub is positioned nearby, integrating relaxation into the outdoor space.

Chalet in Bend

Chalet del Sol - Hot Tub - Ping Pong - Fire pit

Welcome to the cozy Chalet del Sol just South of Old Mill District and close to the hiking trails. What this home offers: ☞ Entire property to yourself ☞ Hot tub ☞ BBQ & Blackstone ☞ Ping Pong Table ☞ Master w/king bed upstairs ☞2nd bedroom downstairs queen bed ☞3rd bedroom is a loft w/queen & 2 twins ☞Two full bathrooms ☞ Fast WIFI ☞ Garage ☞ Fully equipped chef’s kitchen ☞ 65” Smart TV w/ Netflix ☞ Lots of Parking → 4 plus cars ☞ Private yard ☞ Washer + dryer ☞ Ductless heating and cooling

4.92 out of 5 average rating, 615 reviews

A spacious studio apartment is shown, featuring a combination of cozy seating and a dining area. Natural light fills the room through glass doors that lead outside. A bed is visible in the background, creating a functional and inviting living space.

Guest suite in Sunriver

Pepper’s Place

Private marina & hot tub — cozy studio Apt with no shared walls. 7-min drive to the Village at Sunriver via S. Century, 20 mins to Bend, 25 minutes to Mt. Bachelor. SUPs (2), kayaks (2), floats, rafts, and bikes (2 adult + 2 kid), snowshoes (4 pairs). Pepper is a friendly golden/boxer mix who loves kids and dogs. Pet friendly (no fee), fenced yard, hot tub, propane and wood fire pits, OWW. Sound-deadened movie theater and foosball room available upon request. Backyard is shared with Pepper.

4.92 out of 5 average rating, 129 reviews

The modern A-frame cabin is surrounded by snow-covered trees, highlighting its dark exterior. A deck extends around the cabin, accentuated by a row of small evergreen planters against the backdrop of a winter landscape, showcasing the serene setting.

Cabin in Sisters

Popular BBR A-Frame | 2 golf courses | 5 pools

Welcome to Your Modern A-Frame Cabin at Black Butte Ranch! - Accommodations: Sleeps 8 in 2 queen bedrooms and a 2 twin loft, and trundle downstairs - Amenities: Relax in the living area with a Roku TV; the chef's kitchen makes meal prep easy, and self check-in ensures a smooth arrival - Sunny Recreation: Access to 6 pools, including the nearby Paulina pool, plus golf, pickleball, horseback riding, and hiking - Winter Fun: 20m drive to HooDoo Ski Resort Book your unforgettable getaway today!

4.91 out of 5 average rating, 152 reviews

Sunriver cabin near Mt. Bachelor

Come enjoy a get-away in Sunriver where you can relax and unwind or explore all that Central Oregon has to offer. The Cabin on Cooper is ideally located only minutes away from the Deschutes River, golf courses, shopping, Mt. Bachelor, and the Cascade Lakes making it the perfect retreat for large groups, corporate events, and families. When you return from your adventures, enjoy the hot tub and cozy atmosphere, or get competitive with a game of wiffle ball or miniature golf in the backyard.

4.97 out of 5 average rating, 101 reviews

A classic two-story home is presented against a vibrant sunset sky. The wrap-around porch features white columns and is surrounded by neatly trimmed shrubs. Large windows face the yard, allowing for ample natural light to enter the living space.

Home in Sisters

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.

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.

4.93 out of 5 average rating, 226 reviews

Black Duck Cabin

Cozy A frame cabin set in a quiet neighborhood among the pine trees just a short walk from the Deschutes River. The Black Duck Cabin is a perfect destination for all of Central Oregon's amazing activities. 10 minute drive to Sunriver Village, 30 minute drive to Mt. Bachelor, 30 minutes to Downtown Bend, 10 minute walk to the Deschutes River, golfing, fishing, hiking, shopping, mountain biking, all a short drive. If you're looking for a rustic, cabin experience this is the place for you!

Popular amenities for Black Butte Ranch kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

A cozy living area features light-colored walls and a large window providing natural light, framed by blue curtains. A fireplace is situated beneath a wall-mounted television. A wooden coffee table sits centrally, adorned with brochures. Comfortable sofas are arranged around the space.

4.95 out of 5 average rating, 128 reviews

Large Black Bear Cabin in Three Rivers w/ wildlife

The exterior of a charming two-story home is surrounded by tall trees, featuring a welcoming porch with seating. A neatly arranged driveway provides access to a garage, and flower pots line the entrance. Sunlight filters through the branches, creating a serene atmosphere.

4.95 out of 5 average rating, 111 reviews

Deschutes River Getaway-near Bachelor & Sunriver

The exterior of a two-story house is showcased, featuring a mix of dark green and beige siding. A spacious wooden deck is adorned with multiple outdoor seating options, including loungers and a hammock. Tall trees surround the property, contributing to a serene natural setting.

4.92 out of 5 average rating, 105 reviews

Riverfront Cabin

4.93 out of 5 average rating, 196 reviews

A comfortable living area features a green sectional sofa and a gray accent chair. A large coffee table sits in the center, with a light-colored rug beneath. Exposed wooden beams adorn the ceiling, while a staircase leads to an upper level. A television is mounted on the wall.

Home in Old Bend

Drake Park Cottage in the Heart of Bend

A gravel driveway leads to a single-story home nestled among tall pine trees. The house features a neutral exterior and is set back from the road, surrounded by a grassy area, offering a sense of privacy in a tranquil setting.

4.87 out of 5 average rating, 125 reviews

Wooded river retreat near Sun River & Bend

Superhost

A comfortable living area features a sectional sofa and leather ottoman, surrounded by stylish armchairs. Large windows provide views of the surrounding trees, while natural light enhances the space. A neutral color palette is complemented by decorative pillows and a wall art piece depicting a bike.

4.87 out of 5 average rating, 159 reviews

Pet-Friendly Riverfront Home w/ Deck

The outdoor area is surrounded by lush green grass, featuring a fire pit at the center with several blue Adirondack chairs arranged around it. A hot tub is positioned nearby, with a spacious house in the background, framed by tall pine trees.

4.99 out of 5 average rating, 191 reviews

Bend Treehouse • Game Room • Hot Tub • Sleeps 15

The living area features a large sectional couch positioned around a central wagon wheel coffee table. A gas fireplace is set within a stone surround, and a 65” smart TV is mounted on the wall. Natural light fills the space through multiple windows.

4.94 out of 5 average rating, 69 reviews

New 3BR Close to Village! Hot Tub SHARC Pets WFH

Cabin rentals with a kayak

A charming A-frame cabin is surrounded by tall pine trees, featuring a spacious front porch with two rocking chairs and a set of steps leading to the entrance. Large windows allow natural light to fill the interior, enhancing the welcoming atmosphere.

4.95 out of 5 average rating, 66 reviews

Riverwoods A-Frame

A circular fire pit surrounded by six metal chairs is situated in a gravel area. A pathway leads from the fire pit to a two-story lodge, which features a balcony and large windows. Towering pines are visible in the background, and the sky displays hues of sunset.

4.81 out of 5 average rating, 27 reviews

Deschutes Riverfront Home with A/C, Game Room, Hot

4.95 out of 5 average rating, 42 reviews

A-frame w/ hot tub near Mt. Bachelor

An A-frame cabin is showcased with a wooden deck and a sloped roof. Large windows allow natural light to enter, surrounded by tall pine trees. The front door is centrally positioned, adding charm to the home's exterior.

Cabin in La Pine

4.66 out of 5 average rating, 87 reviews

Tall Pines Guest House comes with rental canoe

4.88 out of 5 average rating, 312 reviews

A serene sunset over the Deschutes River is captured, featuring vibrant colors reflecting on the water. Chairs are positioned along the sandy beach, framed by natural vegetation and trees, offering a tranquil riverside view.

Cabin in Old Bend

Amazing, unobstructed River View Downtown Bend

The cabin's exterior features a welcoming entrance with wooden steps leading to a modern door under a spacious, covered porch. Surrounded by tall pine trees, the natural landscape is complemented by stone pathways and a gently sloping yard.

Cabin in Sisters

Black Butte Ranch Ridge Cabin 010

The cozy living room features a large sectional sofa alongside a full sleeper sofa, both positioned around a rustic wooden coffee table. A vibrant area rug complements the warm cabin decor, with natural light streaming through the window and a wooden sliding door visible in the background.

Cabin in La Pine

4.37 out of 5 average rating, 27 reviews

Private La Pine Cabin Rental: 30 Mi to Bend!

A serene view of the river reflects surrounding trees and cabins, with wooden docks leading into the calm water. The soft morning light highlights the greenery along the banks. A kayak is seen gliding across the water, adding to the peaceful ambiance.

4.96 out of 5 average rating, 48 reviews

Sunriver/Bachelor *RiverFront* Cabin

Other holiday rentals with a kayak

An outdoor deck area is shown, featuring a spacious seating arrangement with blue cushions and multiple lounge chairs. A brown dining table is positioned under an orange umbrella, providing shade. Surrounding trees add a natural backdrop, enhancing the overall ambiance.

4.96 out of 5 average rating, 55 reviews

Perfectly located getaway! Walk to the river!

A cozy living area features light wood paneling and large windows. A comfortable sectional sofa, accented with orange and gray pillows, is positioned on a plush area rug. A wood stove adds warmth, while a framed landscape artwork complements the natural tones.

Condo in Sisters

4.78 out of 5 average rating, 146 reviews

Country House Condo with a View

A single-story home is surrounded by greenery, featuring a well-maintained lawn and a gravel pathway. A wooden bench is positioned on the front porch, and large windows provide views into the interior. The structure showcases a sloped roof and a welcoming entrance.

4.91 out of 5 average rating, 95 reviews

Entire Sunriver House, SHARC Passes

The exterior of the single-level home is framed by tall pine trees, providing a natural setting. A covered front porch with seating is visible, inviting relaxation. The garage and pathway are shown along with the structured roofline, reflecting a cozy, welcoming ambiance.

4.95 out of 5 average rating, 20 reviews

13 Stag Lane, Sunriver

5 out of 5 average rating, 10 reviews

Guesthouse in Bend

Peaceful Hobby Farm, Gateway to Outdoor Adventure

Superhost

Home in Sunriver

4.83 out of 5 average rating, 12 reviews

SHARC 8 A/C Bikes Kayaks Tubes BBQ Village