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Cottage holiday rentals in Santiam Pass

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Top-rated cottage rentals in Santiam Pass

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Top guest favourite
The inviting living area features a plush seating arrangement, including a sofa and an armchair, positioned around a wooden coffee table. A brick fireplace adds warmth to the space, and natural light filters through large windows, highlighting the wood-paneled walls and warm wood flooring.
Cottage in McKenzie Bridge

Riverfront Cottage near Loloma/Hotsprings/Hoodoo

From the deck, listen to the Mckenzie River rapids while osprey & eagle soar above. Cozy cottage is right on the banks of the Mckenzie River! Walking distance to local pub, general store & grill in Mckenzie Bridge. 2 min drive to Loloma Lodge & 5 min to Tokatee Golf. 15 min drive east or west to Belknap or Cougar Hotsprings. A stretch more to Proxy, Sahalie & Koosah waterfalls, Blue Pool, or Hoodoo Ski Area. Trails, mountain biking, golf, snow shoes, skiing, rafting, fishing - adventure awaits!

4.97 out of 5 average rating, 218 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!

4.9 out of 5 average rating, 344 reviews
Guest favourite
The exterior view shows a fenced yard with green grass and mature trees in the background. A wooden staircase leads to a covered porch, while a pathway connects to the gate. Natural light and shadows create a peaceful outdoor environment.
Cottage in McKenzie Bridge

Cascadia Cottage-Riverfront near HotSpring& Hoodoo

Hit the hot springs on your way home from skiing! Retreat to the land of big trees, ferns, and the McKenzie River. The cottage is situated on an acre of riverfront property, with 3 bedrooms, 2 baths, and a covered porch that is ideal for drinking coffee and taking in the river views. The home is equipped with a large kitchen and dining room to host family-style meals and gatherings. Whether you’re here to ride singletrack trails, raft the river, or spend quality time with family and friends.

4.94 out of 5 average rating, 155 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.

4.91 out of 5 average rating, 379 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

4.99 out of 5 average rating, 154 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!

4.98 out of 5 average rating, 211 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!

4.98 out of 5 average rating, 156 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.

4.97 out of 5 average rating, 184 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.

4.92 out of 5 average rating, 179 reviews
Top guest favourite
Cottage in Bend

Old Mill Charmer with Hot Tub

The Mill House cottage is one of three historic cottages on this property. It is located in the heart of Bend between the historic downtown and desirable Old Mill district. There is no better location than this one, just steps from Columbia river park and walking distance from the amphitheater, 10 Barrel Brewery, Good Life Brewery, Jackson's Corner and Active Culture. We offer complimentary bikes making it easy for you to zip downtown for your morning coffee or evening happy hour.

4.93 out of 5 average rating, 155 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

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. The kitchen is fully stocked, and I look forward to hosting you!

4.98 out of 5 average rating, 173 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

4.94 out of 5 average rating, 398 reviews

Popular amenities for cottage rentals in Santiam Pass

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

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 Hot Tub✓ Walkable✓

4.95 out of 5 average rating, 492 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

4.95 out of 5 average rating, 317 reviews
Top 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

4.94 out of 5 average rating, 342 reviews
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

5.0 out of 5 average rating, 51 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

4.94 out of 5 average rating, 80 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

4.87 out of 5 average rating, 76 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

4.94 out of 5 average rating, 62 reviews
Guest favourite
The exterior of the cottage features a multi-level wooden deck with railings, providing outdoor space for relaxation. A green umbrella is situated on the deck, and a charcoal grill stands nearby. Large windows on the upper level allow natural light to fill the interior.
Cottage in McKenzie Bridge

River Views, Private Hot Springs Tub, Forest, Deck

4.95 out of 5 average rating, 110 reviews

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

4.88 out of 5 average rating, 466 reviews
Guest favourite
Cottage in Bend

Stylish Downtown Cottage, Walk Everywhere

4.95 out of 5 average rating, 44 reviewsA spacious wrap-around deck is shown, overlooking the serene Mckenzie River. Two outdoor chairs are positioned for relaxing, while picturesque trees frame the scene. The structure features large windows, allowing for ample natural light and views of the tranquil waters beyond.
Cottage in Vida

Lower Mckenzie Riverside Cottage

4.55 out of 5 average rating, 76 reviews
Top guest favourite
A cozy living area is presented, featuring a blue couch and two brown chairs. A wooden dining table is visible, surrounded by wooden chairs. Warm lighting is created by pendant lamps above the table, complemented by a table lamp on a side table. A door leads to the outside.
Cottage in Old Bend

2 Bedroom Delight In The Old Mill

4.91 out of 5 average rating, 175 reviews
Top 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

4.97 out of 5 average rating, 75 reviews
Guest favourite
Cottage in Walterville

Peaceful & Scenic Cottage Near McKenzie River!

4.97 out of 5 average rating, 30 reviewsThe kitchen area features modern dark cabinetry paired with a light countertop. A stylish retro fridge stands against the wall. The space includes a central island with seating, and natural light enters through the nearby window. A cozy fireplace is visible in the corner.
Cottage in Bend

Cute cottage! Hot Tub + near mountain and trails

A cozy cottage is illuminated by decorative lights against a twilight backdrop. Snow blankets the surrounding landscape, while warm light shines from its windows. The structured entrance features a walkway leading to the private garage, highlighting the charming winter ambiance.
Cottage in Bend

Cozy cottage by mtn! 24hr staff, HOT TUB, dogs ok

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

4.91 out of 5 average rating, 502 reviews
Top guest favourite
Cottage in Bend

Upscale Downtown Cottage-EV charger-park and walk

4.98 out of 5 average rating, 131 reviews
Guest favourite
The cottage features a modern exterior with a mix of wood and stone accents nestled among trees. Steps lead up from a garden area with diverse landscaping, providing a natural backdrop. A separate structure is visible in the distance, enhancing the secluded feel of the property.
Cottage in Vida

Stylish Luxurious Relaxing Cottage on the Water

4.94 out of 5 average rating, 54 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

4.79 out of 5 average rating, 139 reviews
Guest favourite
The cottage exterior features a welcoming porch with multiple chairs, surrounded by greenery. A sloped roof with dark shingles complements the white siding, while tall trees frame the property, enhancing the serene atmosphere of the location.
Cottage in Westfir

Westfir River Cottage

5.0 out of 5 average rating, 30 reviews
Guest favourite
The exterior of a forest-green cottage is framed by lush greenery and tall trees. A wooden deck extends to the side, featuring a hot tub and a seating area. A gravel pathway leads up to the entrance, inviting guests to explore.
Cottage in McKenzie Bridge

Spring-Fed Soaking Tub! Lush Central Oregon Haven

4.97 out of 5 average rating, 37 reviewsA charming cottage is displayed under a clear blue winter sky. Snow blankets the ground and surrounds the structure, while soft, warm lighting frames the roofline. The exterior features a combination of neutral tones and a stone chimney, enhancing the cozy winter ambiance.
Cottage in Bend

Popular 2-bedrm at Tetherow, comfy+clean