Cottage vacation rentals in Deschutes County

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, 307 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.

4.98 out of 5 average rating, 184 reviews

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.

Imagine yourself surrounded by majestic old-growth ponderosa pine and juniper trees, where the gentle murmur of Whychus Creek is in the distance, all while being just a short stroll from the vibrant heart of downtown Sisters. Embrace the tranquility as you explore an array of delightful restaurants, local festivals, and enjoy nearby parks, as well as endless hiking and biking trailheads, the Creekside campground, all within moments’ reach. Minutes’ drive to Hoodoo Mountain, Blackbutte, Aspen

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, 335 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.

4.98 out of 5 average rating, 125 reviews

Immaculate, secluded Downtown Cottage-EV charger

25 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, 130 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!

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, 278 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage perfectly 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 that make our town so unique.

4.91 out of 5 average rating, 117 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.

The living area features a cozy sofa and a wooden coffee table atop a woven rug. Large windows invite natural light, while a television is positioned on a wooden stand. A dining area can be seen in the background, enhancing the open layout.

4.93 out of 5 average rating, 123 reviews

Two Bedroom 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.

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, 139 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.

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, 451 reviews

Downtown Bend Home - Walk Anywhere - Firepit- Pets

Riverway Cottage is a charming 2BR/1BA pet-friendly home in Old Bend, just 1/2 block from the Deschutes River. Walk to Downtown, Old Mill, river trails, parks, surf wave, and top breweries. Features include a full kitchen, smart TV, fast Wi-Fi, washer/dryer, fenced yard, BBQ, and fire pit. Private driveway, A/C units, and all essentials included. Ideal for families, couples, work trips, skiers, paddlers, and extended stays. Unbeatable location, comfort, and flexibility.

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, 444 reviews

Vintage Pink Hot Tub✓ Walkable✓

Our 105 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.