Guesthouse vacation rentals in Bend

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Top-rated guesthouse rentals in Bend

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Guest favorite

Guesthouse in Bend

4.98 out of 5 average rating, 502 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.

Oct 14 – 21

ﺩ.ﺇ475 per night

Guest favorite

Guesthouse in Bend

4.96 out of 5 average rating, 699 reviews

A Couples Getaway in Old NW Bend

Old Bend meets new Bend in this spacious, newly constructed second level studio apartment in a century old neighborhood in NW Bend. The beautifully appointed room has private access and includes a well accessorized kitchen, comfortable furnishings, a queen size bed, and bathroom. As comfortable as we know you’ll be in the studio, you must get out and experience all Bend has to offer. Hiking, fishing, golf, lakes, rivers, Mt. Bachelor, beautiful sightseeing and many more activities are within a 30 minute drive. We think you’ll enjoy your stay without getting in your car at all. Within blocks you can visit local brew pubs and a great assortment of restaurants and shops. Beautiful downtown Bend is a 15 minute walk, or, a short bike ride on bikes we provide. Experience locally owned restaurants, bars, breweries, unique boutique shops, coffee roasters, bakeries, Drake park and more. This century old neighborhood which was home to many mill workers in the past has become a rejuvenated and vibrant area for a new generation. Many of the old houses continue to be remodeled and, at the same time, retain the old neighborhood feel.

Dec 11 – 18

ﺩ.ﺇ515 per night

Guest favorite

Guesthouse in Bend

4.93 out of 5 average rating, 641 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.

Jun 1 – 8

ﺩ.ﺇ473 per night

Guest favorite

Guesthouse in Bend

4.97 out of 5 average rating, 188 reviews

Midtown gem~light+bright~park view~full kitchen

Above garage one bedroom/one bath apartment in booming midtown. Open living with a gas fireplace, ac, full-sized kitchen, and gas stove. A large bathroom with a deep tub to relax or let the kids play. The bedroom features a cozy queen bed with a new Tempur-Pedic mattress topper and ample closet space. The east-facing deck is ready to sip your morning coffee while you wake up slowly, grill for an evening in or sit and work with the high-speed wireless as you watch the dog park across the street!

Mar 5 – 12

ﺩ.ﺇ611 per night

Guest favorite

Guesthouse in Bend

4.97 out of 5 average rating, 318 reviews

Quiet 1/1 near river & Old Mill

If you are looking for a quiet neighborhood with a woodsy feel close to the Deschutes River and trail, yet within a mile to the Old Mill shops and restaurants, this is a perfect spot for you! Walk across the street of this newer one bedroom casita to the Deschutes River Trail for a morning hike, afternoon float or picnic. It's fully stocked with everything you should need for your stay. I am happy to provide recommendations for activities and restaurants. I love my home and think you will, too.

Apr 5 – 12

ﺩ.ﺇ615 per night

Guest favorite

Guesthouse in Bend

4.93 out of 5 average rating, 135 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!

Jul 21 – 26

ﺩ.ﺇ559 per night

Guest favorite

Guesthouse in Bend

5.0 out of 5 average rating, 209 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.

Feb 10 – 17

ﺩ.ﺇ516 per night

Guest favorite

Guesthouse in Bend

4.84 out of 5 average rating, 293 reviews

The Local Nest

Experience green tourism while staying at the Local Nest. The local nest was built by us out of re-purposed materials, a shed and lots of love. We also provide you with local products to use while staying here. This is a separate studio (185 sq. ft) with a queen bed, skylights, kitchen, bathroom, and (shared) hot tub. The Midtown location centralizes you so you can drive, ride or walk to Downtown. Pilot Butte a scenic icon is just up the street for watching the sunset!

Jun 30 – Jul 7

ﺩ.ﺇ461 per night

Guest favorite

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.

Jul 5 – 12

ﺩ.ﺇ485 per night

Guest favorite

Guesthouse in Bend

4.99 out of 5 average rating, 518 reviews

Cozy Up! Botanical Studio in the Trees

Wake up to treetop views at this spacious bungalow peppered with live plants, unique art, and a stunning cedar ceiling. Stroll down to the Deschutes River Trail, which can take you downtown. Enjoy the locals-favorite First Street Rapids Park, then curl up and restore on the ultra comfy king bed. Creature comforts abound! No pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

Nov 13 – 20

ﺩ.ﺇ572 per night

Guest favorite

Guesthouse in La Pine

4.94 out of 5 average rating, 108 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.

Mar 5 – 12

ﺩ.ﺇ275 per night

Guest favorite

Guesthouse in Bend

4.94 out of 5 average rating, 289 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!

Sep 24 – Oct 1

ﺩ.ﺇ344 per night