Cottage vacation rentals in Santiam Pass

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, 299 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

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.

4.96 out of 5 average rating, 149 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!

4.98 out of 5 average rating, 180 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.

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,

Cottage in McKenzie Bridge

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.

4.93 out of 5 average rating, 129 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.

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, 126 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!

4.98 out of 5 average rating, 124 reviews

Immaculate, secluded Downtown Cottage-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. 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 brand new. City of Bend Short Term Rental Operating License: STR-20-0285

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, 274 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, 106 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 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, 450 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, 438 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.

4.95 out of 5 average rating, 361 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