Cottage vacation rentals in Bend

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Top-rated cottage rentals in Bend

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

Guest favorite
Cottage in Terrebonne
Quiet central Oregon desert retreat with a view!
Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!
Jan 14 – 21
$126 per night
4.91 out of 5 average rating, 256 reviews
Guest favorite
Cottage in Bend
The Blackberry Cottage
This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.
Mar 6 – 13
$166 per night
4.9 out of 5 average rating, 274 reviews
Guest favorite
Cottage in Bend
In the Heart of Tumalo Two
In the Heart of Tumalo Two is located in a small semi rural community about 10 minutes northwest of Bend Oregon and 15 minutes from Sisters. Ours is one of the oldest buildings in Tumalo and has been completely remodeled and updated. There are local shops, a coffee shop, small grocery store and a Food Truck Court across the street called The Bite. The river is just a couple blocks away. Dogs allowed (only 1) and 50 pounds or under with a $50 pet fee.
May 31 – Jun 7
$115 per night
4.88 out of 5 average rating, 291 reviews

Popular amenities for Bend cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Bend
5 star! Hot Tub+Big Porch w/ Enclosed Yard+Pets OK
Dec 14 – 21
$221 per night
4.93 out of 5 average rating, 230 reviews
Guest favorite
Cottage in Bend
Contemporary Chic, Walk Downtown, Gourmet Kitchen
Aug 18 – 25
$395 per night
4.95 out of 5 average rating, 203 reviews
Guest favorite
Cottage in Bend
Galveston Getaway to all the fun in Bend Oregon
Apr 11 – 18
$193 per night
4.96 out of 5 average rating, 154 reviews
Superhost
Cottage in Bend
New mid century cottage w/ hot tub & view
May 16 – 23
$146 per night
4.77 out of 5 average rating, 120 reviews
Guest favorite
Cottage in Bend
Cozy 3 bedroom house, hot tub, near Sun River
Nov 9 – 16
$200 per night
4.94 out of 5 average rating, 64 reviews
Guest favorite
Cottage in Bend
Cloudchaser Cottage: Cozy Get-Away
Jul 15 – 22
$278 per night
5.0 out of 5 average rating, 13 reviews
Guest favorite
Cottage in Bend
Vintage Pink Hot Tub✓ Walkable✓
Jul 4 – 11
$120 per night
4.94 out of 5 average rating, 385 reviews
Guest favorite
Cottage in Bend
Historic Downtown, Private Hot Tub, High Demand
Aug 10 – 17
$395 per night
4.93 out of 5 average rating, 178 reviews
Guest favorite
Cottage in Bend
One Block to Downtown, Hot Tub, Private Home, Yard
Aug 14 – 21
$409 per night
4.93 out of 5 average rating, 128 reviews
Guest favorite
Cottage in Bend
Guest Favorite! Prime West Side Location, Hot Tub
Apr 5 – 12
$219 per night
4.88 out of 5 average rating, 111 reviews
Guest favorite
Cottage in Bend
Bend's West Side, Walkable, Hot Tub, Fenced Yard
Apr 13 – 20
$199 per night
4.88 out of 5 average rating, 98 reviews
Guest favorite
Cottage in Bend
The Mill Cottage - a perfectly located retreat
Aug 13 – 20
$340 per night
4.95 out of 5 average rating, 91 reviews

Cottage rentals with a pool

Guest favorite
Cottage in Sisters
TruNorthwest Retreat
Feb 1 – 8
$190 per night
4.94 out of 5 average rating, 18 reviews
Guest favorite
Cottage in Redmond
Come Stay and Play at Little Les Cheneaux Retreat
Sep 20 – 27
$212 per night
4.87 out of 5 average rating, 47 reviews
Superhost
Cottage in Bend
Cute cottage! Hot Tub + near mountain and trails
Jan 18 – 25
$283 per night
New place to stay
Guest favorite
Cottage in Sisters
Cottage Live/Play in the Heart of Downtown Sisters
Dec 25 – Jan 1
$277 per night
4.95 out of 5 average rating, 20 reviews
Superhost
Cottage in Bend
Cottage life at Tetherow Resort + HOT TUB, Trails
Sep 22 – 29
$547 per night
New place to stay
Superhost
Cottage in Bend
Popular 2-bedrm at Tetherow, comfy+clean, dogs ok
Sep 28 – Oct 5
$422 per night
New place to stay
Superhost
Cottage in Bend
Comfy mountain cottage at Resort, HOT TUB, dogs ok
Apr 29 – May 6
$563 per night
New place to stay
Superhost
Cottage in Bend
Adorable + comfy! 24hr staff, HOT TUB, dogs
Dec 9 – 16
$438 per night
New place to stay
Superhost
Cottage in Bend
Cozy cottage by mtn! 24hr staff, HOT TUB, dogs ok
Oct 30 – Nov 6
$328 per night
New place to stay
Superhost
Cottage in Bend
Popular cottage at Tetherow! Hot Tub + comfy beds
Feb 11 – 18
$283 per night
New place to stay

Cottage rentals with free parking

Guest favorite
Cottage in Bend
River Camp House
Apr 9 – 16
$158 per night
4.97 out of 5 average rating, 77 reviews
Guest favorite
Cottage in Bend
Blue Spruce Cottage, 2/1, Modern, & Clean.
Mar 12 – 19
$144 per night
5.0 out of 5 average rating, 92 reviews
Guest favorite
Cottage in Sunriver
Cozy Charmer with River Access, 5mins to Village
Jun 1 – 8
$144 per night
4.94 out of 5 average rating, 36 reviews
Guest favorite
Cottage in Sisters
Walk Downtown! Family&Friend Retreat/Sauna
Aug 11 – 18
$297 per night
4.98 out of 5 average rating, 97 reviews
Guest favorite
Cottage in Bend
Exceptional Downtown Cottage-Level II EV charger
Apr 25 – May 2
$169 per night
4.97 out of 5 average rating, 109 reviews
Cottage in Redmond
The West Minister Square Cottage
May 13 – 20
$104 per night
5.0 out of 5 average rating, 4 reviews
Cottage in Sisters
Charming downtown 1BR with inviting deck
Nov 20 – 27
$233 per night
4.24 out of 5 average rating, 34 reviews
Cottage in Redmond
Vibrant 2BR | Patio | Firepit | W/D
Jul 27 – Aug 3
$202 per night
3.75 out of 5 average rating, 4 reviews

Quick stats about cottage rentals in Bend

Total rentals

30 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

4K reviews

Nightly prices starting at

$70 before taxes and fees

Destinations to explore

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