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Our top choices for Chatham holiday homes

1. 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, (18 reviews)
The price is £242
includes taxes & fees
12 Nov - 13 Nov

2. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
The price is £428
includes taxes & fees
16 Nov - 17 Nov

3. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
The price is £100
includes taxes & fees
18 Nov - 19 Nov

4. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
The price is £162
includes taxes & fees
12 Nov - 13 Nov

5. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
The price is £148
includes taxes & fees
19 Nov - 20 Nov

6. Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson
Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to HudsonHudson
10.0 out of 10, Exceptional, (12 reviews)
The price is £275
includes taxes & fees
12 Nov - 13 Nov

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (5 reviews)
The price is £304
includes taxes & fees
18 Nov - 19 Nov

8. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET FriendStottville
The price is £537
includes taxes & fees
17 Nov - 18 Nov

9. Modern Family Home · Walk to Lake · Firepit
Modern Family Home · Walk to Lake · FirepitAthens
10.0 out of 10, Exceptional, (2 reviews)
The price is £408
includes taxes & fees
15 Nov - 16 Nov

10. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to WarrenHudson
10.0 out of 10, Exceptional, (7 reviews)
The price is £322
includes taxes & fees
18 Nov - 19 Nov

11. Charming Hudson Valley Escape | Autumn Vibes & Fire Pit
Charming Hudson Valley Escape | Autumn Vibes & Fire PitClaverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
The price is £420
includes taxes & fees
12 Nov - 13 Nov

12. Modern cabin retreat
Modern cabin retreatCatskill
The price is £189
includes taxes & fees
7 Dec - 8 Dec

13. Cabin Oasis near Town
Cabin Oasis near TownCatskill
The price is £200
includes taxes & fees
12 Nov - 13 Nov

14. 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 £222
includes taxes & fees
12 Nov - 13 Nov

15. Cozy Catskill Escape
Cozy Catskill EscapeCatskill
10.0 out of 10, Exceptional, (2 reviews)
The price is £189
includes taxes & fees
30 Nov - 1 Dec

16. 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 £462
includes taxes & fees
16 Nov - 17 Nov

17. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is £215
includes taxes & fees
13 Nov - 14 Nov

18. Modern Luxurious Cabin, Catskills - The Tiny Nook
Modern Luxurious Cabin, Catskills - The Tiny NookCatskill
10.0 out of 10, Exceptional, (16 reviews)
The price is £246
includes taxes & fees
1 Dec - 2 Dec

19. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
The price is £420
includes taxes & fees
12 Nov - 13 Nov

20. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is £247
includes taxes & fees
15 Nov - 16 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 Chatham
This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.














































































































