A historic building with a prominent clock tower, surrounded by well-maintained lawns and tall trees.

Vacation Homes in Crook County

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Crook County vacation homes

A large wooden barn-style sliding door in a room with light-colored wooden flooring and a blue curtain.

1. Downtown Hub - Dog Friendly

Downtown Hub - Dog Friendly
Redmond
10.0 out of 10, Exceptional, (73 reviews)
"Great house great place to stay! "
United States
Matt w.
Downtown Hub - Dog Friendly
A lodge with multiple buildings, a golf course, and a forested backdrop.

2. Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat

Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat
Bend
9.8 out of 10, Exceptional, (56 reviews)
"Great location and the house was excellent."
United States
John B.
Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat
Living area

3. Old Mill Magic - Hot Tub, A/C, Modern & Updated, Nestled Between Old Mill & Downtown

Old Mill Magic - Hot Tub, A/C, Modern & Updated, Nestled Between Old Mill & Downtown
Southern Crossing
9.6 out of 10, Exceptional, (134 reviews)
"The house was great and in a great location. The house was clean and had plenty of room. The location was amazing. Just a short walk into the old mill district that lots of shopping and restaurants. I would definitely recommend this property to stay at."
United States
Jason P.
Old Mill Magic - Hot Tub, A/C, Modern & Updated, Nestled Between Old Mill & Downtown
A cabin entrance with a wooden sign spelling "CABIN".

4. NW Modern, River, Old Mill near Downtown

NW Modern, River, Old Mill near Downtown
Southern Crossing
9.8 out of 10, Exceptional, (45 reviews)
"Clean quiet cabin to stay at in Bend."
United States
Owen B.
NW Modern, River, Old Mill near Downtown
A covered porch with a blue door, a small table, and a metal railing.

5. Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba

Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
Orchard District
9.4 out of 10, Exceptional, (113 reviews)
"Really cute place and I would definitely stay here again!"
United States
Krista N.
Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
A wooden deck with picnic tables and a barbecue grill.

6. Large 5 Bed , 3bath home close to Deschutes River and Old Mill Shopping District

Large 5 Bed , 3bath home close to Deschutes River and Old Mill Shopping District
Southwest Bend
9.2 out of 10, Wonderful, (114 reviews)
"Our family enjoyed this home for our annual trip, had alittle something for everyone!"
United States
Morgan J.
Large 5 Bed , 3bath home close to Deschutes River and Old Mill Shopping District
An outdoor patio with a wooden table set for dining, a sofa, and a glass door leading to an interior space.

7. HotTub, Near Old Bend & Downtown | Aerie 2BDR King

HotTub, Near Old Bend & Downtown | Aerie 2BDR King
Summit West
10.0 out of 10, Exceptional, (54 reviews)
"Clean place, great location, and great service. Would stay here again"
United States
Spencer S.
HotTub, Near Old Bend & Downtown | Aerie 2BDR King
A two-story house with a covered porch and a patio area.

8. Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District

Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District
Century West
10.0 out of 10, Exceptional, (126 reviews)
"Beautiful home with everything you could think of needing!"
United States
Elizabeth M.
Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District
A single-story house with a green door, a small porch, and a brick entrance.

9. Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
River West
10.0 out of 10, Exceptional, (47 reviews)
"This place is beautiful and the location was excellent! Our hosts were very attentive and the binder of local information was most appreciated!"
United States
Christine R.
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
A modern kitchen with a dining area, wooden cabinets, a black refrigerator, and a ceiling fan.

10. Clean, fully stocked home in Mitchell.

Clean, fully stocked home in Mitchell.
Mitchell
9.8 out of 10, Exceptional, (32 reviews)
"We had a wonderful stay. The kitchen is big and well stocked with wonderful teas and coffee. I would stay again."
United States
Yvonne F.
The price is AED 661
AED 1,021 total
includes taxes & fees
24 Nov - 25 Nov
Clean, fully stocked home in Mitchell.
A hot tub with a view of a mountain range.

11. Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
Terrebonne
10.0 out of 10, Exceptional, (455 reviews)
"Excellent property and location. The views are incredible. The house is very clean and accommodating. Host was excellent in providing quick replies to any questions I had. Would highly recommend and go back!"
United States
Patrick Q.
The price is AED 562
AED 1,141 total
includes taxes & fees
16 Nov - 17 Nov
Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
A pool area with a glass door entrance, stone walls, and a wooden ceiling.

12. Timber & Springs Retreat: Indoor Pool • Hot Tub • Theater Room• Putting Green

Timber & Springs Retreat: Indoor Pool • Hot Tub • Theater Room• Putting Green
Redmond
9.8 out of 10, Exceptional, (62 reviews)
"This was a great property for taking my students on a retreat. It served well for offering an indoor pool, hot tub, plenty of beds, and fun!"
United States
Tess H.
Timber & Springs Retreat: Indoor Pool • Hot Tub • Theater Room• Putting Green
A covered patio area with wooden lattice fencing, stone steps, and a potted plant.

13. Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet

Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet
Larkspur
10.0 out of 10, Exceptional, (42 reviews)
"Small but cute and everything you need for a couple staying for a few days!"
United States
Anonymous traveler
Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet
A two-story house with a covered porch, a chimney, and a well-maintained lawn.

14. Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown

Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown
Old Bend
10.0 out of 10, Exceptional, (45 reviews)
"Great location and perfect for 1or 2 people."
United States
Mike L.
Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

15. New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views

New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views
Bend
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 496
AED 841 total
includes taxes & fees
12 Nov - 13 Nov
New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views
A single-story house with a gray exterior, a front door, and a small porch.

16. Cozy Downtown Redmond Cottage

Cozy Downtown Redmond Cottage
Redmond
9.4 out of 10, Exceptional, (29 reviews)
"What a great location, walk all over town for coffee in the morning and food and drinks in the evening. Home is well stocked and comfortable."
United States
Taylor H.
Cozy Downtown Redmond Cottage
A hot tub on a wooden deck with a forest view.

17. New! Westside Home ~ Hot Tub ~ Dog Friendly ~ Location, Location, Location!

New! Westside Home ~ Hot Tub ~ Dog Friendly ~ Location, Location, Location!
River West
9.8 out of 10, Exceptional, (12 reviews)
"Perfect outdoor dining for guests plus family."
United States
Rick P.
New! Westside Home ~ Hot Tub ~ Dog Friendly ~ Location, Location, Location!
A hot tub area with a view of a forested hillside and a river.

18. Bend River Retreat

Bend River Retreat
Boyd Acres
9.8 out of 10, Exceptional, (170 reviews)
"Great place, great location and amazing view."
United States
Jaime P.
Bend River Retreat
A hotel room with a large bed, a desk with a lamp, and a wardrobe.

19. Huckleberry Cottage - A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage

Huckleberry Cottage - A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage
River West
9.6 out of 10, Exceptional, (134 reviews)
"Great house. Great location. Everything we wanted."
United States
Jeff G.
Huckleberry Cottage - A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage
A kitchen with dark wooden cabinets, a stainless steel sink, and a marble countertop.

20. ***NEW*** Charming home located in Downtown Bend!

***NEW*** Charming home located in Downtown Bend!
River West
9.8 out of 10, Exceptional, (9 reviews)
"5 stars"
United States
Angelica L.
***NEW*** Charming home located 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 Crook County Hotel Reviews

Best Western Bend North

Best Western Bend North

10/10 Excellent
"I loved it all great place to stay breakfast was amazing"
Christina 4-night trip
Posted 1 hour ago
Best Western Bend North

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