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Apartments

Condos
Our top choices for East Canaan holiday homes

1. Peaceful and cozy 1 bed 1 bath in quaint Winchester
Peaceful and cozy 1 bed 1 bath in quaint WinchesterWinchester
10.0 out of 10, Exceptional, (4 reviews)
The price is AU$271
includes taxes & fees
10 Nov - 11 Nov

2. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is AU$577
includes taxes & fees
19 Nov - 20 Nov

3. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
The price is AU$390
includes taxes & fees
9 Nov - 10 Nov

4. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (41 reviews)
The price is AU$454
includes taxes & fees
9 Nov - 10 Nov

5. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AU$425
includes taxes & fees
8 Nov - 9 Nov

6. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
The price is AU$526
includes taxes & fees
5 Nov - 6 Nov

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
The price is AU$502
includes taxes & fees
5 Nov - 6 Nov

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$941
includes taxes & fees
16 Nov - 17 Nov

9. Maya's Garden House
Maya's Garden HouseGreat Barrington
The price is AU$1,643
includes taxes & fees
18 Nov - 19 Nov

10. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 reviews)
The price is AU$400
includes taxes & fees
5 Nov - 6 Nov

11. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
The price is AU$1,777
includes taxes & fees
15 Nov - 16 Nov

12. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
The price is AU$881
includes taxes & fees
9 Nov - 10 Nov

13. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great BarringtonGreat Barrington
The price is AU$1,821
includes taxes & fees
6 Nov - 7 Nov

14. Chic Barn Style * Fireplace * Near Stissing House
Chic Barn Style * Fireplace * Near Stissing HousePine Plains
10.0 out of 10, Exceptional, (3 reviews)
The price is AU$960
includes taxes & fees
11 Nov - 12 Nov

15. Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
The price is AU$1,153
includes taxes & fees
23 Nov - 24 Nov

16. Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Chic Lakeside Oasis|Near Rhinebeck & MillbrookStanfordville
The price is AU$926
includes taxes & fees
16 Nov - 17 Nov

17. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine Plains
10.0 out of 10, Exceptional, (15 reviews)
The price is AU$1,923
includes taxes & fees
5 Nov - 6 Nov

18. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is AU$1,785
includes taxes & fees
11 Nov - 12 Nov
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.
Learn more about East Canaan
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