Cottage vacation rentals in Santiam Pass

A spacious backyard is shown, featuring a well-maintained lawn bordered by shrubs and trees. A wooden patio table with an umbrella is visible on the deck, alongside a lounging area. The fenced yard offers a sense of privacy and openness.

4.93 out of 5 average rating, 283 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.

Cottage in McKenzie Bridge

A cozy green cottage features a wrap-around deck, surrounded by tall trees and natural greenery. Sunlight filters through the branches, creating a warm ambiance. A patio umbrella provides shade over the outdoor seating area, inviting relaxation in the serene setting.

4.96 out of 5 average rating, 113 reviews

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!

4.95 out of 5 average rating, 419 reviews

Vintage Pink Hot Tub✓ Walkable✓

NOTE: Thru June ongoing road construction is scheduled on Portland Ave. Please read Other Things to Note below before booking :-) 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 bathtub, wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.

4.99 out of 5 average rating, 154 reviews

A private hot tub is situated on a stone patio, surrounded by rustic wooden fencing. The entrance to the cottage is visible, framed by a charming blue door and a welcoming sign. Comfortable outdoor seating is arranged nearby, enhancing relaxation in the serene environment.

Cottage in Silverton

Silver Falls Cottage · Hot Tub · Near State Park

Cottage on a working farm - minutes from Silver Falls State Park. Enjoy bucolic surroundings while sitting in the private hot tub or around the fire pit. In our rural location cell phone service is not available nor is Wi-Fi. Come to The Cottage to disconnect and reconnect with your family and the outdoors (a landline is provided). There is a maximum of 4 guests allowed to stay at this property - adults and children included! Because of safety children under 5 cannot be accommodated.

Cottage in McKenzie Bridge

A peaceful riverside scene showcases a pair of Adirondack chairs positioned among lush green foliage. Towering trees, covered in moss, frame the flowing McKenzie River, creating a tranquil setting for solitude and relaxation.

4.93 out of 5 average rating, 112 reviews

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.

4.92 out of 5 average rating, 234 reviews

A charming country cottage is nestled among trees, featuring a triangular roof and a front porch with railing. Two windows and a central door enhance the inviting exterior. Natural wood accents contribute to the rustic appearance, blending seamlessly with the surrounding woodland.

Cottage in Stayton

Cozy Cottage Near Silver Falls -1 bedroom w/Loft

This "one bedroom plus the loft as the 2nd bedroom country cottage is so cozy and functional, and nestled in the foothills of the Cascades. You will love getting away to this wooded cottage with all of the amenities of home. Take a stroll through the woods or visit the onsite pond with Paddle boat, barbeque grill and gazebo with picnic table. Also come meet our horse - Sugarbear, and our sweet Donkey (Shewee). You will be able to enjoy privacy as the cottage is nestled in the woods.

4.98 out of 5 average rating, 158 reviews

A wooden sauna, designed in an oval shape, is positioned in a private outdoor area. Two slatted lounge chairs with blue and white striped cushions are placed nearby, set against a backdrop of green grass and trees, creating a peaceful retreat.

Cottage in Sisters

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

IMAGINE WALKING A FEW MINUTES TO THE HEART OF DOWNTOWN, YET STILL NESTLED AMONGST OLD-GROWTH PONDEROSA PINES IN A SERENE SETTING, NATURES BEAUTY ALL AROUND TO TAKE IN. Various restaurants, local festivals, parks, hiking and biking trailheads, Fives Pines Resort and Spa, Creekside campground, and an athletic center are moments away. Minutes drive to Hoodoo Mountain, Black Butte Resorts, Aspen Golf Course, and Eagle Airport. Extensive free off-road parking, RV parking, and internet.

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.

4.94 out of 5 average rating, 117 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 living area features a light-colored hardwood floor, complemented by a sectional sofa adorned with blue cushions. A wooden coffee table sits center stage, while a dining table for four and a stainless-steel kitchen appliances complete the welcoming space. Natural light floods through multiple windows.

4.99 out of 5 average rating, 119 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.

A charming cottage is set on a well-maintained lawn, showcasing a welcoming entryway with a wooden door and large front windows. The exterior features a combination of light green siding and rich brown accents, surrounded by trees and shrubs that enhance the inviting appearance.

4.94 out of 5 average rating, 233 reviews

Historic Downtown, Private Hot Tub, High Demand

This amazing little downtown cottage provides all the comforts of home with the freedoms of vacationing. You cannot find a better location than The Autumn Cottage! It is located on a quiet little street, yet it is just one block from the historic downtown area. It has been lovingly designed to offer guests the full flavor of Bend, with many modern amenities paired with classic charm to make your Bend visit exceptional.

4.97 out of 5 average rating, 119 reviews

Exceptional Downtown Cottage-Level II EV charger

24 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" 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. These significant investments keep the Cottage fresh and like it was brand new. City of Bend Short Term Rental Operating License: STR-20-0285

The interior space features warm wooden flooring and white walls. A black wood-burning stove is positioned against one wall. A small round dining table with wooden chairs can be seen, alongside a doorway leading to a bathroom and a kitchen area. A spiral staircase adds an element of charm.