Cottage vacation rentals in Sisters

The bathroom features white subway tiles on the walls, complemented by a glass shelf and mirror above a small, curved sink. A showerhead is visible above, alongside a wall-mounted storage rack. The space is well-lit, emphasizing its clean and functional design.

4.93 out of 5 average rating, 288 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, 165 reviews

A serene view of Whychus Creek meanders through a lush landscape, framed by vibrant green trees. Sunlight filters through the foliage, casting dappled shadows on the water's surface, creating a calm and inviting atmosphere in nature.

Cottage in Sisters

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

Image yourself surrounded by magestic 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, enjoy nearby parks, endless hiking and biking trailheads, the Creekside campground, and the fitness center, which are moments away. Minutes’ drive to Hoodoo Mountain, Blackbutte,

A wide shot captures a snow-covered mountain, with gentle slopes blanketed in fresh powder. The surrounding forest is adorned with snow-laden trees, and a soft pastel sky marks the horizon. The scene conveys a serene winter landscape, perfect for outdoor enthusiasts.

4.98 out of 5 average rating, 112 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!

4.92 out of 5 average rating, 126 reviews

A wooden deck is shown, featuring a large rocking chair and a smaller plastic chair. The entrance leads into the cottage with a view of the dining area in the background. Natural wood siding enhances the rustic charm, surrounded by trees.

Cottage in La Pine

“Peaceful Pines Cottage” 2+ acres near Mt. Bach

Peaceful Pines Cottage is a newly renovated PET FRIENDLY remote cottage located in Central Oregon. Perfect for ski trips at Mt. Bachelor & Willamette Ski Resort! This 3 bedroom / 2 full bathroom home is on 2.25 acres of fully fenced-in land that backs up to public BLM land for you to explore.. Driving distance to downtown La Pine, Bend, PCT trails, Crater Lake National Park, lakes + much more! This is the perfect home for a gathering with loved ones or a relaxing weekend for yourself.

4.96 out of 5 average rating, 262 reviews

A lush green landscape is depicted, showcasing a serene park area with vibrant trees and flowering bushes. A peaceful water body can be seen in the background, where people are engaged in recreational activities. Light filters through the foliage, enhancing the natural beauty.

Cottage in Old Bend

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.

4.93 out of 5 average rating, 121 reviews

A light-filled room features wooden floors and white shiplap walls. A round table with black chairs is positioned next to a workspace with a simple desk and wooden chair. Shelves are filled with books, while a vase with flowers adds a natural touch.

Cottage in Old Bend

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 bathroom features dual sinks on a sleek countertop, complemented by stylish fixtures. Two mirrors reflect the bright space, while natural light enters through a nearby window. Neutral tones and high-quality finishes create a clean and functional environment.

4.99 out of 5 average rating, 123 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.

5 out of 5 average rating, 102 reviews

A popcorn container filled with various snacks, including candy bars and popcorn, is placed on a countertop. Two remote controls are located next to the container, and a light switch is visible on the wall in the background.

Cottage in Prineville

~Quail Run Cottage~

**Please read full description & look at all pictures to ensure it’s the right fit for your needs** This little gem is in the prime location. Located in the country but 5 minutes from the town of Prineville. It offers beautiful open views and nature all around. Take a load off & soak in the private hot tub & enjoy the scenery, it will not disappoint. Enjoy watching the quail run around the property along with other wildlife. **Please note- There is no washer/dryer/oven**

An above-ground hot tub is situated in the private yard, surrounded by snow-blanketed ground. Steam gently rises from the bubbling water, creating a serene atmosphere. A wooden fence encloses the yard, providing privacy, while a storage shed is visible in the background.

4.95 out of 5 average rating, 420 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 charming porch features a vibrant green door framed by two windows. A small square table and two chairs are positioned on the wooden deck, accompanied by potted flowers. A striped mat and comfortable seating enhance the inviting entrance.

4.95 out of 5 average rating, 349 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

4.97 out of 5 average rating, 124 reviews

An outdoor seating area is featured under a canopy, equipped with comfortable gray couches and a fire pit at the center. Soft lighting is provided by strand lights along the structure. A hot tub is visible in the corner, contributing to a relaxing atmosphere.

Cottage in Sunriver

Cozy Home w/River Access, Hot Tub, 5min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.