A large, layered mountain with distinct geological formations.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Prineville cottages

A single-story house with a dark blue exterior, a front door, two windows, and a small porch.

1. Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park

Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park
River West
9.8 out of 10, Exceptional, (161 reviews)
"Great location!"
United States
Marc H.
The price is €198
includes taxes & fees
6 Oct - 7 Oct
Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park
A two-story house with a garage, a well-maintained front yard with landscaping, and a clear sky.

2. Bend Home w/ Patio + Fire Pits < 3 Mi to Dtwn

Bend Home w/ Patio + Fire Pits < 3 Mi to Dtwn
3.0 star property
Mountain View
Bend Home w/ Patio + Fire Pits < 3 Mi to Dtwn
A brick building with a storefront, circular windows, and a sign that reads 'SCHUTTS'.

3. Cottage along Deschutes River Trail w Epic Views

Cottage along Deschutes River Trail w Epic Views
River West
9.4 out of 10, Exceptional, (10 reviews)
"Great place to stay. Centrally located. Right on the river. "
United States
Tracey T.
The price is €197
includes taxes & fees
11 Oct - 12 Oct
Cottage along Deschutes River Trail w Epic Views
A two-story house with a front porch, a chimney, and a well-maintained lawn.

4. Oak Millhouse - Beautifully restored home in Downtown Old Bend

Oak Millhouse - Beautifully restored home in Downtown Old Bend
Old Bend
10.0 out of 10, Exceptional, (6 reviews)
"I love this place! Clean, lovely, dead end street, backyard, close to town and great food, close to skiing, and great bathtub i will be staying here again"
United States
Loryn Z.
Oak Millhouse - Beautifully restored home in Downtown Old Bend
A wooden building with a covered patio, a stone wall, and a well-maintained lawn.

5. North Sister - Bungalow Charm, Fireplace, Queen bed, Parking

North Sister - Bungalow Charm, Fireplace, Queen bed, Parking
Old Bend
9.4 out of 10, Exceptional, (6 reviews)
"Perfect place for a night to work/visit Bend. Lovely neighborhood."
United States
Amy M.
North Sister - Bungalow Charm, Fireplace, Queen bed, Parking
A deck with a hot tub, barbecue grill, and outdoor seating area with umbrellas.

6. Contemporary Chic │West Side │Walk Everywhere │Hot Tub │One Block to River

Contemporary Chic │West Side │Walk Everywhere │Hot Tub │One Block to River
River West
9.8 out of 10, Exceptional, (53 reviews)
"Host was great. Was so clean and ready when we got there. Perfect place for 2 people and a dog."
United States
Bonnie H.
The price is €283
includes taxes & fees
18 Oct - 19 Oct
Contemporary Chic │West Side │Walk Everywhere │Hot Tub │One Block to River
A single-story house with a front porch, a garage, and a well-maintained lawn.

7. Historic Downtown Location │Heart of Bend │Walk Everywhere │Hot Tub │High Demand

Historic Downtown Location │Heart of Bend │Walk Everywhere │Hot Tub │High Demand
Old Bend
9.4 out of 10, Exceptional, (78 reviews)
"Great location, easy to walk everywhere and nice park for the dog across the street"
United States
Ryan B.
Historic Downtown Location │Heart of Bend │Walk Everywhere │Hot Tub │High Demand
A single-story house with a front porch, a red door, and a mailbox.

8. Historic Downtown │Walk Everywhere │Private Hot Tub │One Block to River

Historic Downtown │Walk Everywhere │Private Hot Tub │One Block to River
River West
9.6 out of 10, Exceptional, (91 reviews)
"Nice bungalow in great location."
United States
Donna T.
The price is €308
includes taxes & fees
6 Oct - 7 Oct
Historic Downtown │Walk Everywhere │Private Hot Tub │One Block to River
A single-story cottage with a front porch, a small window, and a garage.

9. Westside Cottage │Fenced Yards │Hot Tub │One Block to Galveston │Guest Favorite

Westside Cottage │Fenced Yards │Hot Tub │One Block to Galveston │Guest Favorite
River West
9.8 out of 10, Exceptional, (73 reviews)
"Yes perfect place to stay ."
United States
Arthur G.
The price is €297
includes taxes & fees
6 Oct - 7 Oct
Westside Cottage │Fenced Yards │Hot Tub │One Block to Galveston │Guest Favorite
A small wooden house with a dark door, two Adirondack chairs outside, and a stone pathway leading to the entrance.

10. Trendy West Side │Walk to Breweries & Food Carts │Hot Tub │Fenced Outdoor Space

Trendy West Side │Walk to Breweries & Food Carts │Hot Tub │Fenced Outdoor Space
River West
10.0 out of 10, Exceptional, (66 reviews)
"Perfect Location!!"
United States
Rocky A.
The price is €292
includes taxes & fees
18 Oct - 19 Oct
Trendy West Side │Walk to Breweries & Food Carts │Hot Tub │Fenced Outdoor Space
front view

11. Walk to downtown and amphitheater

Walk to downtown and amphitheater
River West
9.6 out of 10, Exceptional, (43 reviews)
"The Drake Club was great! Really nice little cottage that is well decorated and includes a great kitchen and bathroom. The location is excellent as you are a short walk/bike ride to everything Bend has to offer. The Drake Club is a great little spot in Bend and I would highly recommend it to anyone considering a stay in Bend!"
United States
Brian S.
Walk to downtown and amphitheater
A two-story house with a front porch, a chimney, and a well-maintained lawn.

12. Fir Millhouse - Lovely historic cottage in downtown Bend

Fir Millhouse - Lovely historic cottage in downtown Bend
Old Bend
9.8 out of 10, Exceptional, (12 reviews)
"Clean, efficient apartment, with comfortable bedding, clean bathroom with ample toiletries, functional kitchen and great location. Quiet street with on site parking, and easy walk to many great spots in Old Bend. "
United States
Anonymous traveller
The price is €201
includes taxes & fees
6 Oct - 7 Oct
Fir Millhouse - Lovely historic cottage in downtown Bend
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Prineville Hotel Reviews

Trailhead Lodge

Trailhead Lodge

10/10 Excellent
"Great room. I had neighbors on both rooms sharing a wall but you’d never know it. The place was super quiet, clean and comfy."
Rebecca 2-night trip
Posted 1 hour ago
Trailhead Lodge

Find out more about Prineville

Prineville Cottages information

Number of reviews
264
Accommodation
96 Cottages
Lowest Price
€197
Highest Price
€308

Frequently asked questions

Why book your cottage in Prineville with Expedia?
Reserving a cottage in Prineville is as simple as deciding on your travel dates and picking an ideal place for a getaway in the outdoors. From luxurious retreats to affordable stays and cottages that feature perks like a pool, Expedia has something for all styles and tastes. As for the best deals around? We have them too!
How can I find cheap cottages in Prineville?
With Expedia's convenient filter tool, locating cheap cottages in Prineville has never been simpler. To find accommodation that'll make your wallet smile, fine-tune your search results by star rating, budget and amenities.
What is there to do in Prineville near my cottage?
Once you've unpacked and settled in, head out and discover the incredible things Prineville has for you to experience. Ochoco Wayside State Park is a top attraction to add to your to-do list.