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Guesthouse vacation rentals in Bend

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Top-rated guesthouse rentals in Bend

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Bend
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.
$66 per night
Guest favorite
Guesthouse in Bend
Midtown gem! Park view-full kitchen-gas fireplace!
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!
$111 per night
Guest favorite
Guesthouse in Bend
Kathy's Westside Perch
Perched among the trees this 650+ sq ft dedicated guest suite has a private entrance, a wall of windows, queen size bed, Wi-Fi, Hulu/Netflix, self check-in/ keyless entry. Near Mt. Bachelor. Downtown and the Old Mill District are both less than 2 mi away. Discover restaurants, breweries, shopping, art galleries, theaters, and more! With Mt. Bachelor resort, hiking and fishing just minutes up the road, you will relish your stay in the heart of Central Oregon! No room tax for stays of 30+days.
$72 per night

Popular amenities for Bend guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Bend
Quiet 1/1 near river & Old Mill
$122 per night
Guest favorite
Guesthouse in Bend
Artist Studio with sleeping Loft
$86 per night
Guest favorite
Guesthouse in Bend
Romantic Guest House w/Hot Tub, Pool, Tennis court
$119 per night
Guest favorite
Guesthouse in Bend
Cabin on quiet 3 acres 10 min to downtown Bend.
$84 per night
Guest favorite
Guesthouse in Bend
Cozy Bookworm's Retreat in Bend
$112 per night
Guest favorite
Guesthouse in Bend
Cozy & Convenient Downtown Cottage
$69 per night
Guest favorite
Guesthouse in Bend
Live the Pastoral Idyll in a Warm and Inviting Guesthouse
$109 per night
Guest favorite
Guesthouse in Bend
Country Apartment, Tumalo 2BR
$75 per night
Guest favorite
Guesthouse in Bend
Close to everything! Oasis on edge of west Bend
$77 per night
Superhost
Guesthouse in Bend
The Bivouac of Bend
$171 per night
Guest favorite
Guesthouse in Bend
Quiet peacful country living close to everything!
$125 per night
Guest favorite
Guesthouse in Bend
Country Cottage Close to Town
$65 per night

Guest house rentals with a patio

Superhost
Guesthouse in Bend
Modern & Bright 1 Bedroom Guesthouse near Old Mill
$67 per night
Guest favorite
Guesthouse in Bend
Cozy & Luxurious Guest House in the Heart of Bend!
$149 per night
Superhost
Guesthouse in Bend
The Rhoda - Brand new custom Downtown studio
$75 per night
Guest favorite
Guesthouse in Bend
Mtn Modern 1 BR Bungalow at Old Mill
$122 per night
Guest favorite
Guesthouse in Bend
Artisan's Woodsy Studio Cabin
$110 per night
Guest favorite
Guesthouse in Bend
Brand new, modern 1 bdrm + loft with open land!
$99 per night
Guest favorite
Guesthouse in Bend
Cozy Guesthouse with Large Kitchen
$100 per night
Guest favorite
Guesthouse in Terrebonne
Modern lofted guest house
$89 per night
Guest favorite
Guesthouse in Bend
Adorable 1-bedroom 1930s farmhouse.
$118 per night
Guest favorite
Guesthouse in Redmond
Redtail Retreat
$104 per night
Superhost
Guesthouse in Sisters
Downtown Sisters Suite - Hot Tub - Dog Friendly
$105 per night
Guest favorite
Guesthouse in Bend
Modern Pilot Butte Getaway
$170 per night

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Bend
Ranch Cottage: Desert, Forest, Horses, Hot Tub
$103 per night
Guest favorite
Guesthouse in Bend
Suburban Forest guest house with garage
$93 per night
Guest favorite
Guesthouse in Bend
Private Standalone, Hot Tub, Contemporary Chic
$142 per night
Guest favorite
Guesthouse in Bend
West Hills Hideaway
$139 per night
Guest favorite
Guesthouse in Bend
Private apt. nestled in the Ponderosa Pines
$71 per night
Guest favorite
Guesthouse in Bend
BlueSpruce Guesthouse-Walkable RiverTrail/Downtown
$132 per night
Guest favorite
Guesthouse in Bend
Private country escape with mountain views!
$137 per night
Guest favorite
Guesthouse in Redmond
Modern Downtown Cottage near Outdoor Adventure
$92 per night
Guest favorite
Guesthouse in Bend
Bend Ranch Guesthouse on 20 acres
$139 per night
Superhost
Guesthouse in Redmond
The Downtown Guesthouse
$68 per night
Guest favorite
Guesthouse in Terrebonne
Compound Coziness...Terrebonne Guesthouse
$100 per night
Guest favorite
Guesthouse in Terrebonne
15 min from SmithRock pets allowed affordable spot
$60 per night

Quick stats about guesthouse rentals in Bend

Total rentals

70 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

9.9K reviews

Nightly prices starting at

$50 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Deschutes County
  5. Bend
  6. Guesthouse rentals