A sunset over a calm lake with a large industrial structure and distant mountains.

Vacation Homes in Columbia County

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Columbia County vacation homes

A wooden barn with a gabled roof, large open garage doors, and a visible interior with a table and chairs.

1. New Year's Eve is now open! Ring in 2027 at beautiful Bellavista Country Estate!

New Year's Eve is now open! Ring in 2027 at beautiful Bellavista Country Estate!
Old Chatham
9.6 out of 10, Exceptional, (100 reviews)
"The house was very interesting with quirky art all around the house that kept us entertained. The games room and ping pong were a lot of fun and the gym was well equiped. The bedrooms were built as suits so it took a little planning of who slept where as you had to go through one bedroom to get to another bedroom. There are 3 rooms/ 8 people who have to share one bathrooms due to the layout. Host helped with suggestions on resturants etc and the house has lots of brochures on things to do....
United States
Vanessa
New Year's Eve is now open! Ring in 2027 at beautiful Bellavista Country Estate!
A wooden interior with a door leading to a room, a mirror on the wall, and a heater on a table.

2. Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake
Copake Lake
9.2 out of 10, Wonderful, (5 reviews)
"A very nice spot!"
United States
Elizabeth S.
Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake
A wooden dock with two white chairs facing a calm lake, surrounded by greenery and a cloudy sky.

3. Ski Season is right around the corner!!! Come join us by the firepit!!

Ski Season is right around the corner!!! Come join us by the firepit!!
Copake
9.4 out of 10, Exceptional, (26 reviews)
"House was very nice and in a great location. Was perfect for a long weekend while attending a family wedding. "
United States
Kevin B.
Ski Season is right around the corner!!! Come join us by the firepit!!
A living room with a sofa, a coffee table, and a kitchen area with bar stools.

4. COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Craryville
9.6 out of 10, Exceptional, (45 reviews)
"Stay was great easy check in check out great communication from host."
United States
Darcy J.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

5. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 1,388
AED 2,509 total
includes taxes & fees
22 Nov - 23 Nov
NEW RENO Historic Creamery in Berkshires w/hot tub
A camping setup with a metal chair and a table by a river in a forest.

6. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AED 735
AED 1,263 total
includes taxes & fees
27 Oct - 28 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A spacious living room with a high ceiling, skylights, a large TV, and a cozy seating area.

7. Blue Bird Chalet – 5BR Retreat w/ Sauna, Pool + Loft, Near Jiminy Peak

Blue Bird Chalet – 5BR Retreat w/ Sauna, Pool + Loft, Near Jiminy Peak
East Chatham
8.8 out of 10, Excellent, (3 reviews)
"Very unique home it was quite and peacfull"
United States
heidi L.
Blue Bird Chalet – 5BR Retreat w/ Sauna, Pool + Loft, Near Jiminy Peak
A wooden deck with a staircase leading to a covered porch area.

8. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is AED 390
AED 519 total
includes taxes & fees
1 Nov - 2 Nov
All the comforts of home
A couple in a hot tub with a natural landscape in the background.

9. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is AED 955
AED 2,147 total
includes taxes & fees
27 Oct - 28 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A wooden deck with outdoor furniture, a red umbrella, and a view of the sunset over a grassy landscape.

10. Million Dollar Catskill Mountain Sunset Views - 6 Miles from Hudson Warren St.

Million Dollar Catskill Mountain Sunset Views - 6 Miles from Hudson Warren St.
Hudson
Million Dollar Catskill Mountain Sunset Views - 6 Miles from Hudson Warren St.
A spacious kitchen with a large island, wooden flooring, and white cabinetry.

11. Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
New Lebanon
10.0 out of 10, Exceptional, (15 reviews)
"House was perfect and the owner was extremely responsive. Would definitely stay here again!"
United States
Denise H.
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
Living Room

12. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
Mtn-View Retreat in Huson Valley: Great for Groups
A log cabin with a deck and outdoor seating area, surrounded by a lush green landscape and dense forest.

13. Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
East Chatham
8.6 out of 10, Excellent, (14 reviews)
"We had a fantastic stay - lovely house, beautiful weather and just nice to get away from everything for a few days. Would definitely stay again."
United States
Heather B.
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

14. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is AED 735
AED 1,652 total
includes taxes & fees
27 Oct - 28 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A spacious log cabin interior with a large living area, a kitchen, and a dining area.

15. Modern Log Chalet - 10 acres, views, and a pond!

Modern Log Chalet - 10 acres, views, and a pond!
Chatham
10.0 out of 10, Exceptional, (8 reviews)
"Our stay here was amazing. The house was immaculate and well stocked with everything. The property was beautiful and the location was convenient for our trip to Catamount. Our host was very responsive and answered all our questions. We would definitely stay here again! "
United States
Jennifer B.
Modern Log Chalet - 10 acres, views, and a pond!
A large white house with a two-story porch and a covered bridge over a pond.

16. Private Estate, Guest House, Playroom, Gym, Theater | Sunny Pond by Avantstay

Private Estate, Guest House, Playroom, Gym, Theater | Sunny Pond by Avantstay
Austerlitz
10.0 out of 10, Exceptional, (143 reviews)
"Great house in a beautiful setting."
United States
Paul B.
Private Estate, Guest House, Playroom, Gym, Theater | Sunny Pond by Avantstay
A view through a window with a metal frame, overlooking a parking area with several cars, a grassy field, and a building in the distance.

17. Bellwether on Main: Comfort, Resilience, Passive House; an AAC building

Bellwether on Main: Comfort, Resilience, Passive House; an AAC building
Hillsdale
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay in Hillsdale! Thank you, Dan!Look forward to another visit!"
United States
Shelagh M.
Bellwether on Main: Comfort, Resilience, Passive House; an AAC building
A modern building with a balcony, large windows, and a metal railing.

18. Hudson Valley and The Berkshires getaway

Hudson Valley and The Berkshires getaway
Hillsdale
10.0 out of 10, Exceptional, (15 reviews)
"Very comfortable home in a great area!"
United States
Karen V.
Hudson Valley and The Berkshires getaway
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

19. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 764 total
includes taxes & fees
1 Nov - 2 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A lakeside picnic area with a wooden bench and picnic table, a sign indicating no lifeguard on duty, and a trout daily limit sign.

20. Charming cottage with lake access, wood burning fire place, and WiFi

Charming cottage with lake access, wood burning fire place, and WiFi
Elizaville
9.2 out of 10, Wonderful, (15 reviews)
"Clean and comfortable, many amenities, feels like home."
United States
Sandra C.
Charming cottage with lake access, wood burning fire place, and WiFi
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 Columbia County Hotel Reviews

Howard Hotel

Howard Hotel

10/10 Excellent
"Lovely hotel. Great location."
Bridget 1-night trip
Posted 12 hours ago
Howard Hotel

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