Holiday rentals with a fireplace in Sisters

4.98 out of 5 average rating, 931 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!

4.93 out of 5 average rating, 355 reviews

The exterior of a rustic A-frame cabin features wooden siding and a sloped roof, surrounded by tall Ponderosa trees. A spacious porch with outdoor furniture invites relaxation, while double French doors provide access to the living area. Distinctive architectural details enhance the cabin's charm.

Cabin in Bend

Quaint A-Frame Cabin close to Mt Bachelor

Cosy two story A-Frame cabin among Ponderosa trees in a quiet residential. 5 minutes drive to Sunriver Village, 16 min. Mt Bachelor, 20 m Bend downtown. Living room has a comfy sectional, a single reclining armchair and TV. My cabin has a well appointed kitchen, laundry room with W/D, a Bathroom/Shower downstairs. A 2 bedrooms upstairs with Queen size bed. There is a powder room/toilet upstairs in the hallway. NO SMOKING/NO PARTIES /4 MAX .Please leave my home how you found it. Thank you 😄

4.99 out of 5 average rating, 126 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 a block or two 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.

4.99 out of 5 average rating, 527 reviews

A charming tiny log cabin is nestled amidst tall evergreen trees, gently blanketed in snow. The cabin's sloped roof is thick with snow, creating a cozy appearance. A path through the white snow leads toward the cabin's entrance, inviting exploration in a serene winter landscape.

Cabin in Bend

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

A well-lit dining area features a long table surrounded by tall chairs, with cushions in warm tones. A modern light fixture hangs above, while natural light shines through skylights and large windows, highlighting a decorative wall piece and a workspace nearby.

4.99 out of 5 average rating, 149 reviews

Quail Park Haven in NW! King Beds & Hot Tub

Relax in this peaceful NW Bend home with king beds and access to Quail Park. Enjoy natural light from the skylights and high ceilings. Kick back in the expansive backyard with mature plantings, tall trees and flagstone paths. Multiple patios including a deck off the living room, a paver patio with fire-pit, hot tub, outdoor furniture and gas BBQ. EV charger, HEPA air filter and garage access. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

4.98 out of 5 average rating, 323 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.

4.89 out of 5 average rating, 225 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.

Condo in Sisters

Sisters Getaway

Welcome to Sisters! This 2 bedroom, 2 bath condo is situated in the Pine Meadows development & 7 min walk to downtown Sisters. Sunny corner unit on main flr. Open-concept living w/ 9ft ceilings, gas fireplace & recently remodeled w/ new appliances. Amazing primary suite w/walk-in closet & private deck Downtown Sisters has restaurants, antiques, bike shops & Sisters Coffee Shop. Pool, hot tub, tennis courts, & sculpted walking path offer views of the magnificent 3 Sisters mountain range.

5 out of 5 average rating, 152 reviews

An open-plan living space features a wooden dining table surrounded by white chairs, complemented by a decorative plant in a pot. Natural light filters through a skylight and windows, enhancing the wooden beams and soft color palette of the room.

Cabin in Sisters

Modern Mountain Cabin Close to Town (HOT TUB!)

Come enjoy this beautiful home filled with tons of natural light, skylights, a cozy fireplace and a highly functional open floor plan. The backyard features a newly built deck and outdoor dining, BBQ, patio loungers, fire pit and HOT TUB! All the benefits of a quiet neighborhood while being just a 5 - 10 minute walk from the heart of downtown Sisters and a short drive to endless hikes and running trails, beautiful lakes and rivers, skiing, rock climbing, mountain biking and so much more.

5 out of 5 average rating, 269 reviews

A bright living area is filled with natural light from large windows. The cozy sofa offers a relaxed seating option, complemented by a stylish ottoman. A well-equipped kitchen features modern fixtures, and exposed wood details enhance the warm and inviting ambiance.

Tiny home in Redmond

Close to Smith Rock, Mountain View, Country Charm

The Tiny House at Aspen View Farm is just what you need! Great location for exploring beautiful Central Oregon - Smith Rock is only 15 min away. On a unique 14 acre farm, relax and retreat with tranquil Cascade Mountain and country views, say hi to Roo the farm dog, and watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, a/c, heated floors & more! Please read full listing before booking so there are no surprises :)

4.96 out of 5 average rating, 142 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!

4.97 out of 5 average rating, 175 reviews

The RV interior features a spacious living area with a large sectional sofa and a central kitchen island. Modern appliances, including a stovetop and refrigerator, are visible, along with ample cabinetry. Windows provide natural light, framed by simple curtains, and a soft area rug adds comfort.

Campervan/RV in Bend

Glamping! Quad Slide RV on a Tumalo Hobby Farm

Welcome to the Tumalo hobby farm! Here you will have your own 42ft 2019 Forest River RV, located on our lovely Tumalo property. Nestled in the midst of goats and chickens, this will be a perfect landing for work or play. Enjoy the mountain views and bright stars after your day out adventuring around Central Oregon. Within close driving distance to Bend, Sisters, Redmond, Mt Bachelor and Hoodoo. This RV is fully hooked up with power, water, heat, A/C, internet, and is ready for you.

4.89 out of 5 average rating, 222 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.

Popular amenities for Sisters Accommodation with Fireplace

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fireplace

The exterior of the home features a welcoming front porch with two black Adirondack chairs and a small table. A path leads to the front door, bordered by low-maintenance landscaping and a natural stone feature. Large windows provide views of the surrounding area.

4.99 out of 5 average rating, 303 reviews

Your gateway to Mt Bachelor & all that Bend offers

4.97 out of 5 average rating, 206 reviews

A modern kitchen features green cabinetry and a large marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are prominently displayed. Natural light flows in through nearby windows, enhancing the open layout adjacent to a cozy living area.

Home in Sunriver

Walk to Everything! Hot tub, SHARC passes

The exterior of the two-story cabin features a charming combination of wood and siding. A welcoming porch with seating is visible, framed by manicured landscaping. Above, a private balcony invites relaxation, showcasing the property’s connection to the surrounding natural beauty.

5 out of 5 average rating, 280 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

4.87 out of 5 average rating, 456 reviews

The living area features a brick fireplace as a focal point, surrounded by comfortable seating options. A coffee table sits in front of a couch with a soft throw. Natural light enters through large windows, and a door leads to the exterior.

Home in Redmond

The Little Red Chimney House - 3 BR 2 BA

4.95 out of 5 average rating, 698 reviews

A cozy living area features a leather couch facing a propane stove, with a warm fire flickering. Two wooden stools are positioned at a small table, and a stack of magazines is displayed on a wooden coffee table. Natural light filters through the window.

Home in Redmond

"Little Pine Cabin" attached to my home.

An aerial view captures the proximity of the property to downtown Bend, with notable landmarks and tree-lined streets visible. The layout highlights a clear walking path leading to the town center, showcasing a mix of residential and commercial buildings amidst greenery.

4.99 out of 5 average rating, 315 reviews

"Urban Spruce" - Great peaceful location!!

A spacious living room features a light-colored sectional sofa positioned around a glass coffee table. Large windows invite natural light, revealing a view of the outdoors. A stone fireplace provides a warm focal point, complemented by a cozy armchair and decorative elements throughout.

4.99 out of 5 average rating, 183 reviews

Airy Bend Oasis - Two Ensuites

Superhost

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.

Home in Sisters

4.73 out of 5 average rating, 140 reviews

Tollgate Cabin in the Pines (with Level 2 Charger)

Apartment rentals with a fireplace

A modern living area showcases a comfortable dark sofa alongside a bright orange armchair. A wooden coffee table is positioned in front, with a small plant and speaker on top. A dining table with four chairs is visible in the background, and a fireplace adds warmth to the space.

4.93 out of 5 average rating, 103 reviews

Modern Condo~Fireplace~Walk to Old Mill & River

An open-concept living space features a large kitchen island with bar stools and modern appliances. Natural light enters through multiple windows, highlighting a cozy seating area with a sectional sofa. Wooden accents and a stylish rug add warmth to the contemporary design.

5 out of 5 average rating, 101 reviews

Craftsman Style Retreat in Bend River West

4.98 out of 5 average rating, 126 reviews

A spacious living area is equipped with a comfortable sofa, armchairs, and a sleek coffee table. Large windows allow natural light to fill the room, while a modern ceiling fan circulates air. The adjacent dining area features a table set for four, creating an inviting social space.

Apartment in Old Bend

Delightful 2 bd steps to river

The exterior of the modern, detached apartment is shown, featuring a muted green facade and a sloped roof. Two garage doors are visible at the bottom, framed by flowering trees that add a touch of nature to the setting. A clear blue sky provides a bright backdrop.

4.8 out of 5 average rating, 295 reviews

Steps from downtown! Private, modern apartment

4.96 out of 5 average rating, 114 reviews

The exterior of the two-story apartment is framed by tall pine trees, showcasing a robust wooden structure. A private entrance and garage are visible, while a deck extends from the second story, offering an inviting extension of the living space.

Apartment in Bend

Spring River Guest Apartment

The living room area features a red leather sofa and a small wooden coffee table, situated on a richly patterned area rug. A staircase with wooden railings leads to the upper loft. Natural light enters through windows positioned above, illuminating the space.

4.95 out of 5 average rating, 914 reviews

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

A private duplex home is shown, featuring a well-maintained exterior with vertical siding in neutral tones. A garage door is visible, along with a side entryway and utility meters. The driveway and surrounding landscape convey a quiet residential setting.

4.94 out of 5 average rating, 206 reviews

A Stone's Throw | Hillside Loft

4.93 out of 5 average rating, 339 reviews

A comfortable living area features a dark gray sofa positioned in front of a stone fireplace. A simple coffee table sits on a patterned area rug, and a dining table is visible in the background. The space is complemented by a lofted sleeping area with a ladder for access.

Apartment in Old Bend

The Hub—Apartment @ Downtown & Historic Dist

Villas with a fireplace

4.92 out of 5 average rating, 13 reviews

An open concept living area features a striking stone fireplace and a grand piano. Large floor-to-ceiling windows provide expansive views of the outdoors. Wood accents and vaulted ceilings enhance the space, while a cozy leather sofa and area rug invite relaxation.

Villa in Redmond

Cascade Lookout

4.96 out of 5 average rating, 84 reviews

A cozy bedroom features a spacious bed adorned with decorative pillows, alongside a wooden chair with floral accents. A desk with a lamp is positioned near a window, which is dressed with light curtains. A vibrant landscape painting is displayed on the wall opposite the bed.

Private room in Bend

Room @ Sorrento 1 of 3