Compare Crook County Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Crook County

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

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

Bend OR
$191 nightly
The price is $214 total per night
$214 total
Dec 17 - Dec 18
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Air conditioning
Historic Downtown Location │Heart of Bend │Walk Everywhere │Hot Tub │High Demand

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

Bend OR
At this cottage, guests have access to free WiFi in public areas, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Hot Tub
Kitchen
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries

Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries

Bend OR
Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This family-friendly cottage also has barbecue grills.
Kitchen
Washer
Aspen House- Sweet, Modern Downtown Cottage, 100+mbps Wifi, A/C, Walk Everywhere

Aspen House- Sweet, Modern Downtown Cottage, 100+mbps Wifi, A/C, Walk Everywhere

Bend Oregon
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills. This family-friendly cottage also has a garden.
Kitchen
Washer
Redmond House w/ Community Amenities Access

Redmond House w/ Community Amenities Access

3 out of 5
Redmond OR
Guests staying at this cottage enjoy an outdoor pool, free WiFi in public areas, and barbecue grills. A stay here includes free parking. This smoke-free cottage also has a garden.
Pool
Kitchen
Sleeps 20, 4 Units 10bdr, Hot Tub, Near Old Bend + DT Aerie by Avantstay

Sleeps 20, 4 Units 10bdr, Hot Tub, Near Old Bend + DT Aerie by Avantstay

3 out of 5
1212 Skyline Ranch Rd Bend OR
$1,687 nightly
The price is $1,892 total per night
$1,892 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
This cottage features free WiFi in public areas and barbecue grills. Free parking is available if you drive.
Kitchen
Washer
Hike, Fish & Ski: Redmond Escape w/ Hot Tub!

Hike, Fish & Ski: Redmond Escape w/ Hot Tub!

3 out of 5
Redmond OR
Guests of this cottage enjoy features like an outdoor pool, free WiFi in public areas, and an arcade/game room. Free parking is included with your stay. This smoke-free cottage also has barbecue grills.
Pool
Kitchen
Eagle Crest Retreat w/ Great Wifi & Resort Access!

Eagle Crest Retreat w/ Great Wifi & Resort Access!

3 out of 5
Redmond OR
$382 nightly
The price is $418 total per night
$418 total
Dec 17 - Dec 18
Total with taxes and fees
Guests of this cottage enjoy features like an outdoor pool, free WiFi in public areas, and an arcade/game room. If you drive, take advantage of free parking. This family-friendly cottage also has barbecue grills.
Pool
Kitchen
Vintage Awbrey- Fireplace, Hot Tub, AC, 100+mbps Wifi, Bikes, Walk Downtown

Vintage Awbrey- Fireplace, Hot Tub, AC, 100+mbps Wifi, Bikes, Walk Downtown

Bend OR
Guests staying at this cottage enjoy a water park, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Hot Tub
Kitchen
Don't see what you're looking for?
See all available properties in Crook County
View all properties
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.

Cottages

Book a cottage in Crook County
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Crook County. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Crook County better.

Cottage apartments in Crook County range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Crook County
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Crook County and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Crook County cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Crook County. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Crook County Cottages essential information

Accommodation
92 Cottages
Lowest Price
$214
Highest Price
$1,892
Popular accommodation
Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park, Historic Downtown Location │Heart of Bend │Walk Everywhere │Hot Tub │High Demand, Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries, Aspen House- Sweet, Modern Downtown Cottage, 100+mbps Wifi, A/C, Walk Everywhere, Redmond House w/ Community Amenities Access, Sleeps 20, 4 Units 10bdr, Hot Tub, Near Old Bend + DT Aerie by Avantstay, Hike, Fish & Ski: Redmond Escape w/ Hot Tub!, Eagle Crest Retreat w/ Great Wifi & Resort Access!, Vintage Awbrey- Fireplace, Hot Tub, AC, 100+mbps Wifi, Bikes, Walk Downtown

More to Explore