Cottage holiday rentals in Bend

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.

4.93 out of 5 average rating, 337 reviews

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

Located in the heart of NW Bend in the middle of it all! A short walk to great restaurants + pubs, the river, Amphitheater, Downtown, 3 Parks, The Old Mill -but on a nice quiet street. Well worth the price, it sleeps a comfortable 4 and a cozy 6 with a comfty Queen bed in one room, and pine bunk bed in other room (full bed on bottom and top with cozy mattresses). Large enclosed yard for the pets and patio with Hot tub! The home is well stocked, tastefully furnished with high quality bedding.

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, 361 reviews

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.

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.

4.87 out of 5 average rating, 462 reviews

Historic Old Town Cottage, walkable Downtown Bend

Welcome to the Sweet Spot of Bend — our 1917 logging-era cottage in the heart of Old Town. You're half a block from the surf wave on the Deschutes River, and an easy stroll to downtown, the Old Mill District, and Drake Park. Lovingly restored with historic character and modern comforts, a fenced yard for the dogs, and off-street parking. Float the river, walk home from a concert at the Amphitheater, catch the Mt. Bachelor shuttle to ski. Sleeps up to 6 — your basecamp for the best of Bend.

4.98 out of 5 average rating, 129 reviews

Upscale Downtown Cottage-EV charger-park and walk

26 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" Rated as “Exceptional” 5 Star reviews for all vacation rentals in the Bend area. The Cottage is constantly being updated including new furniture, appliances, paint, and even painting of the cabinets. A new mini split A/C and Heating system will be installed in August, 2025.These significant investments keep the Cottage fresh and like it was new. City of Bend Short Term Rental Operating License: STR-20-

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.

4.98 out of 5 average rating, 143 reviews

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, 179 reviews

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.

4.92 out of 5 average rating, 155 reviews

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.

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.

4.99 out of 5 average rating, 143 reviews

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 for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

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.

4.97 out of 5 average rating, 153 reviews

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, boot warmer, grill, and new washer/dryer. Driveway and extra street parking (free). Fast WiFi and a smart TV. The kitchen is fully stocked, and we look forward to hosting you!

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.

4.95 out of 5 average rating, 311 reviews

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.

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.

4.95 out of 5 average rating, 476 reviews

Vintage Pink Hot Tub✓ Walkable✓

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.

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.

4.94 out of 5 average rating, 390 reviews

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

Popular amenities for Bend cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.92 out of 5 average rating, 146 reviews

Old Mill Charmer with Hot Tub

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.

4.96 out of 5 average rating, 68 reviews

Cozy Sisters Cottage | Pool • Walk to Town • Dogs

A 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.

Popular cottage at Tetherow! Hot Tub + comfy beds

A 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.

Popular 2-bedrm at Tetherow, comfy+clean

A cozy cottage is framed by fresh snowfall under a twilight sky, with warm lights accentuating the exterior. The building features a stone chimney and a welcoming entrance, complemented by a snow-covered pathway and surrounding shrubs.

Comfy mountain cottage at Resort, HOT TUB, dogs ok

A charming cottage is depicted with a sloped roof and inviting front porch. Adjoining chairs sit on a lush green lawn, surrounded by well-maintained shrubs and seasonal flowers. A stone pathway leads to the entrance, framing the structure in a serene outdoor setting.

4.97 out of 5 average rating, 37 reviews

Cottage Live/Play in the Heart of Downtown Sisters

An outdoor patio area is surrounded by a wooden fence, featuring a round black table with four chairs, a vibrant red umbrella, and a coffee table. Colorful flowers and greenery are planted along the edges, creating a serene outdoor space.

4.88 out of 5 average rating, 168 reviews

Guest Favorite! Prime West Side Location, Hot Tub

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.

5 out of 5 average rating, 48 reviews

Hot Tub, Fire Pit, Dog Friendly

Pet-friendly cottage rentals

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.

4.92 out of 5 average rating, 170 reviews

2 Bedroom Delight In The Old Mill

4.99 out of 5 average rating, 140 reviews

Epic Waterfront Home, walk to Downtown & Old Mill!

4.95 out of 5 average rating, 476 reviews

Vintage Pink Hot Tub✓ Walkable✓

The exterior of the home is framed by lush greenery, showcasing a well-maintained lawn. A welcoming porch features steps leading up to the front door, flanked by a small seating area and flower pots, enhancing the inviting look of the rental.

4.94 out of 5 average rating, 444 reviews

An Urban Base to Bend's Adventures!

The 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.

Cute cottage! Hot Tub + near mountain and trails

4.9 out of 5 average rating, 361 reviews

The Blackberry Cottage

4.95 out of 5 average rating, 38 reviews

Stylish Downtown Cottage, Walk Everywhere

4.95 out of 5 average rating, 311 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

Private cottage rentals

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.

4.79 out of 5 average rating, 138 reviews

New mid century cottage w/ Mountain View

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.

4.9 out of 5 average rating, 488 reviews

Downtown, Modern Nostalgia--walk to shops, cafes

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.

4.98 out of 5 average rating, 203 reviews

Minutes walk Downtown/Cozy Cottage Retreat/Sauna.

A spacious kitchen area is highlighted by modern Smeg appliances and dark cabinetry. A large island offers stool seating, while natural light illuminates the space. A cozy seating area with a gray couch sits nearby, complemented by a decorative fireplace and wall art.