Guesthouse holiday rentals in Deschutes County

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Deschutes County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse in Bend

4.98 out of 5 average rating, 503 reviews

Live the Pastoral Idyll in a Warm and Inviting Guesthouse

Located in a quiet, rural hamlet, this enchanting casita is quaint yet contemporary. Windows on all sides, combined with modern lighting, create a bright and welcoming space. Settle into a classic Adirondack chair and admire the bucolic landscape. Up to two Kids stay free! Our additional guest charge is waived for up to two children. Either adjust your reservation guest count just to reflect the adults in the group (minus up to two children) and message me the details of your party or send me a request and we can adjust the rate. The casita is an inviting newly remodeled space. The front living space has a fold down couch with all the bedding provided to turn this into a cozy second sleeping area. The wall mounted television has access to local cable, Netflix and Hulu. You can also rent a movie with Vudu without leaving the house! Just login or create an account and enjoy. The kitchenette has a full sized fridge to keep all of the famous Bend beer cold that you bring home to enjoy. Enjoy a cup of coffee or tea on us!! We have a Keurig and provide a selection of beverage choices for our guests. The casita also has a hot plate, toaster oven, microwave and BBQ and a selection of dishes & pots and pans if you feel like cooking during your stay. The bedroom has a very comfortable King size pillow top mattress, a dresser, night stands. Some hanging storage and a luggage rack. The room is easily large enough to accommodate a porta crib (we have on available for use) or additional small child's sleeping mat. We welcome well behaved pets to stay at our airbnb. We ask that pets stay off the furniture during your visit. Please enjoy the space. The patio area outside of the Airbnb is for our guests to enjoy. You are welcome to explore the pastures outside of the Airbnb. Please make sure you close any gates behind you, we have friendly horses who many be in the area and come to say hello. Our home is located on the property, but it is not physically connected to the Airbnb space. We get to meet many of our guests in the driveway as we are taking care of things outside. We are always available by text or phone. We have pets (dogs/cats/horses) who live on the property as well. Our Rottweiler, Mia is very friendly and is around frequently to see if she can make new friends with our guests. She always is looking for someone to give her a pet, be aware once you start petting her she really like to lean into people and can catch you off balance if your not prepared. Please let me know if you, or the pets traveling with you, have concerns with interactions with our dogs and we can make arrangements to have them more contained during your stay. Despite its rural setting, the house is only a few minutes by car from all of Bend's amenities. Closer to home, Cascade Village and the neighborhood of Tumalo are just a mile away. Hiking, biking, fishing and golf are popular activities. Looking for some provisions? Just 1 mile down Hwy 20 east towards Bend take a left on Robal road to access the cascade village shopping center. Groceries: Trader Joe’s, Food 4 Less, and Target are all located here. Trailhead liquor store just across Hwy 97 at Robal road (Oregon only sells beer and wine in the grocery store) Dining: Shinsei Sushi, Little Pizza Paradise, El Rancho Grande, Moose Sister’s, Olive Garden or cross Hwy 97 for Kefi fresh, Cracker Barrel & MOD pizza. Grab and go: Starbucks, Chipotle, Chick Fil-a, Taco DelMar, Togo’s, Jamba Juice. Or cross Hwy 97 for Black Rock Coffee Bar (try a cronut, their awesome!) To explore Central Oregon you will need a car. The Airbnb is a quick drive to many area attractions. In about 30 minutes or less you can be at Smith Rock, Mt. Bachelor, headed into the Cascade Lakes or many of the other hiking or Mountain bike trails in the area. The cute community of Tumalo is 1 mile west on Hwy 20. Stop in at the Bite, enjoy the sunshine, food trucks and a selection of local beer or hop across the street to Tumalo Cider and same their local cider in their new tasting room (Dry is my favorite). Keep going west on Hwy 20 and in less than 20 miles you will arrive in the picturesque community of Sisters where you can easily spend an afternoon exploring the shops and enjoying the magnificent view of the mountains.

Guest favourite

Guesthouse in Bend

4.93 out of 5 average rating, 646 reviews

Artisanal Tiled Custom Built w/Hot tub & Livestock

Our artistic studio is located on a small family farm with a country feel yet close to everything Bend has to offer. Outside we have a pig, chickens, large fenced yard, hot tub, beautiful views. Inside you'll find tons of tile mosaics, stainless steel appliances, hand built European cabinets, Heated floors, custom walk in shower, lots of plants and original artwork. You will have a private studio with no shared spaces that includes a queen bed, kitchen, living room, bathroom, lawn and hot tub.

Guest favourite

Guesthouse in Bend

4.94 out of 5 average rating, 540 reviews

Private apt. nestled in the Ponderosa Pines

Nestled among the Ponderosa pines, this newly constructed apartment is a relaxing getaway after a day enjoying Central Oregon. The apartment is completely separate from the main house and comes with a/c and heating. The bedroom has a queen bed. Kitchen has a refrigerator, coffee pot, countertop convection oven, microwave oven and counter top cooktop burner. Large deck with seating and gas grill. Located 2 miles from Peterson Ridge trails, 5 miles from Sisters, 15-25 mins to Bend.

Guest favourite

Guesthouse in Terrebonne

4.98 out of 5 average rating, 103 reviews

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

Guest favourite

Guesthouse in Bend

5.0 out of 5 average rating, 211 reviews

Private country escape with mountain views!

Looking for a clean, private getaway in the Central Oregon outdoor wonderland? Five minutes from Pine Nursery Park and Big Sky sports fields, this light-filled, second story space has a private deck where you can enjoy your morning coffee while taking in views of the Cascade Mountains. Completely fenced area at ground level for the doggos, and you can walk them along the canal road on the property. Awesome dedicated Wifi, and a private, completely separate space from the owner.

Guest favourite

Guesthouse in Bend

4.93 out of 5 average rating, 137 reviews

Private Studio w/ Hot Tub near the Deschutes River

The Fresca Studio has a kitchenette, hot tub, BBQ & bikes. Downtown Bend is a few miles away, McKay cottage, Deschutes River Trail & Sawyer park are a short walk, and all things Bend eat, drink, biking, hiking, skiing are all close by. The studio is separate from the main house w/ a private entry & patio, fully furnished, and easy access to/from the highway and parkway. Not suitable for children under 5y/o, 2 guests only and children are considered guests. No pets. See you soon!

Guest favourite

Guesthouse in Bend

4.95 out of 5 average rating, 158 reviews

The Outpost Bend

The Outpost is a seperate guest home located on our 10 acre hobby farm. It offers spectacular views of the Cascades, stunning sunsets and a peaceful, private location 15 minutes east of downtown Bend. The property adjoins public land, and is on a quiet country road. Our family lives onsite with our 3 sons, dogs, hens, and sheep. The Outpost has a private driveway, use of basketball court, and a lovely private outdoor seating area. 45 min drive to Mt. Bachelor.

Guest favourite

Guesthouse in Bend

4.98 out of 5 average rating, 231 reviews

Ranch Cottage: Desert, Forest, Horses, Hot Tub

Beautiful guest cottage studio, with mountain views, in the southeast Bend neighborhood of Sundance. 15 minutes to town and 45 minutes to Mt. Bachelor ski area. This special ranch property is two blocks away from endless recreation in the Deschutes National Forest. Come hike, bike, ride, explore caves, ski, snowshoe, and more right from the door of your private cottage. Includes one king Sleep Number bed and one queen Murphy bed. Private hot tub out the back door.

Guest favourite

Guesthouse in Bend

4.96 out of 5 average rating, 237 reviews

Quiet peacful country living close to everything!

Quite country living close to town! Extremely peaceful and park like setting on 2.5 acres just 5-6 miles to anywhere in town. Studio has a pool table and large fenced outdoor area with horseshoe pits and close to private access trails for walking or riding your bike. Full kitchen, full bath and private closet. My place is good for couples, solo adventurers, business travelers, and furry friends (pets). Maximum of 2 pets allowed. NO PARTIES WILL BE TOLERATED.

Guest favourite

Guesthouse in Redmond

4.98 out of 5 average rating, 194 reviews

Modern Downtown Cottage near Outdoor Adventure

This beautifully designed cottage is located in Downtown Redmond walking distance from several quaint coffee shops and restaurants, and only fourteen minutes to Smith Rock and less than ten minutes to the Redmond Airport. Hoping to visit Bend? In less than 20-minutes you can be in downtown or floating on the Deschutes River. Whether you're looking for an outdoor adventure or just a quiet, clean, and safe place to rest, our cottage will meet your needs.

Guest favourite

Guesthouse in La Pine

4.95 out of 5 average rating, 112 reviews

Ponderosa Pines Bunkhouse - Dog friendly ADU

Bring your favorite person, your animals and have some fun! The Little Deschutes River is a short walk away down a dirt road. Come and enjoy outdoor recreation and quiet nights under the stars. After a good snowfally, you can snowshoe from the door into backcountry BLM land. Easy drive into Bend for some entertainment or the mountain ski slope for a day of shredding.

Guest favourite

Guesthouse in Bend

4.95 out of 5 average rating, 292 reviews

Cabin on quiet 3 acres 10 min to downtown Bend.

Enjoy the peaceful serenity of our guest house. Enjoy a large lawn, irrigation pond with deck for hanging out, and a firepit. Our home is 10 minutes drive to downtown Bend; 45 minutes to Mt Bachelor; 40 minutes to Smith Rock; 20 minutes to Phil's trailhead for mountain biking (All times are without rush hour traffic). Come enjoy all that Bend has to offer!