Guesthouse vacation rentals in Bend

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Top-rated guesthouse rentals in Bend

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Guest favorite

Guesthouse in Bend

4.96 out of 5 average rating, 740 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.

Guest favorite

Guesthouse in Terrebonne

4.86 out of 5 average rating, 224 reviews

15 min from SmithRock pets allowed affordable spot

close to smith rock. In the crooked river ranch community. golf course, tennis court, store, 3 bars, all 5 minutes away. Newly renovated guest house. We do live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky to please refrain from booking, as this is definitely not a luxury hotel in the city. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Guest favorite

Guesthouse in Bend

4.99 out of 5 average rating, 107 reviews

Renovated Condo - Ideal Location

This is Central Oregon's premier location for recreation activities. Your stay at this sleek condo will have you encircled by peaks, lakes, meadows, culture, adventure, breweries, festivals, family fun and more. Offering a cozy condo that comfortably sleeps 2 guests with a queen size bed, a mini kitchen, the convenience of on-site laundry facilities. Plus, a living/dining are comforts that would be hard to find in an average hotel. Come make this your launching pad as you experience Bend!

Guest favorite

Guesthouse in Bend

4.98 out of 5 average rating, 399 reviews

Bend Ranch Guesthouse on 20 acres

Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.

Guest favorite

Guesthouse in Bend

4.96 out of 5 average rating, 365 reviews

BlueSpruce Guesthouse-Walkable RiverTrail/Downtown

The Blue Spruce is a charming, private second story guest house . It is accessed by exterior stairs, private entrance, and self check in. It is cozy, equipped with a full kitchen, sunny living room, 1 BD, and 1 Bath. Convenient location in a quiet neighborhood by downtown Bend, less than a mile to the river trail, coffee shops, brew pubs, and grocery. Great launching pad for mountain biking, hiking, skiing, golfing, fishing, whitewater and countless other adventures, you get the picture!

Guest favorite

Guesthouse in Terrebonne

4.98 out of 5 average rating, 134 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 favorite

Guesthouse in Terrebonne

4.9 out of 5 average rating, 262 reviews

Compound Coziness...Terrebonne Guesthouse

Come and join us in gorgeous Central Oregon! The guesthouse is part of our 5 acre property that we live on with our two friendly dogs. Your house has a private fenced in area, but you are welcome to explore the entire property and watch gorgeous sunsets of the Cascade Range. This house provides a queen bed in one room, and a double and twin bunk bed in the second room. A full kitchen and washer/dryer gives you the convience to make this your home during your visit.

Guest favorite

Guesthouse in Bend

4.99 out of 5 average rating, 286 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 favorite

Guesthouse in Sunriver

4.98 out of 5 average rating, 552 reviews

Riverfront on Deschutes River

Located ON the Deschutes River, private above garage apartment with deck. Quiet, private unit. 5 miles to Sunriver Resort, attend events-GET AWAY FROM THE CROWDS! Easy 20 mile drive to Bend, close to Cascade Lakes area and Three Sisters Wilderness for great hiking. 23 miles to Mt Bachelor. EV charger ChargePoint 40 amp One block to Deschutes Nat’l forest and a trail along the river.

Superhost

Guesthouse in Bend

4.91 out of 5 average rating, 173 reviews

Kingston Kottage

Kingston Kottage is conveniently located in the heart of Bend's popular west side. Just a 5-10 minute walk from some of Bend's best restaurants and breweries and a 15-minute walk or 5-minute bike ride to downtown Bend. Super private, clean, comfortable, and quiet! The Kottage is available for a minimum rental period of 30-days. perfect for an extended visit to Bend.

Guest favorite

Guesthouse in Bend

4.95 out of 5 average rating, 304 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!

Guest favorite

Guesthouse in Bend

4.97 out of 5 average rating, 350 reviews

Old Mill and River Walk Retreat

Located in the heart of Bend, you are walking distance to the River trail, Old Mill Districts wonderful shops and restaurants, several parks and Les Schwab Amphitheater. Very easy access to Cascade Lakes Highway, Phils trail, Mt Bachelor and all the outdoor adventuring you will need. Short drive or beautiful 2 mile river trail walk to Downtown Bend!