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Our top choices for Hillsdale vacation homes

1. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (41 reviews)
The price is ¥34,033
¥50,158 total
includes taxes & fees
Nov 9 - Nov 10

2. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
The price is ¥16,733
¥20,859 total
includes taxes & fees
Nov 4 - Nov 5

3. 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 ¥31,512
¥52,271 total
includes taxes & fees
Nov 3 - Nov 4

4. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is ¥27,935
¥64,116 total
includes taxes & fees
Nov 3 - Nov 4

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 ¥31,906
¥47,430 total
includes taxes & fees
Nov 3 - Nov 4

6. 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 ¥89,195
¥189,740 total
includes taxes & fees
Nov 4 - Nov 5

7. 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 ¥63,024
¥105,069 total
includes taxes & fees
Nov 16 - Nov 17

8. Maya's Garden House
Maya's Garden HouseGreat Barrington
The price is ¥140,492
¥198,290 total
includes taxes & fees
Nov 3 - Nov 4

9. 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)
The price is ¥31,512
¥51,352 total
includes taxes & fees
Nov 3 - Nov 4

10. 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 ¥11,029
¥30,831 total
includes taxes & fees
Nov 3 - Nov 4

11. 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 ¥13,393
¥33,372 total
includes taxes & fees
Nov 5 - Nov 6

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 ¥59,715
¥104,013 total
includes taxes & fees
Nov 10 - Nov 11

13. Modern cabin retreat
Modern cabin retreatCatskill
The price is ¥20,806
¥38,837 total
includes taxes & fees
Nov 3 - Nov 4

14. 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 ¥142,004
¥210,018 total
includes taxes & fees
Nov 8 - Nov 9

15. Cabin Oasis near Town
Cabin Oasis near TownCatskill
The price is ¥21,901
¥42,025 total
includes taxes & fees
Dec 1 - Dec 2

16. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is ¥122,109
¥206,202 total
includes taxes & fees
Nov 9 - Nov 10

17. 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 ¥32,300
¥68,725 total
includes taxes & fees
Dec 1 - Dec 2

18. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)
The price is ¥60,267
¥102,087 total
includes taxes & fees
Nov 3 - Nov 4

19. Creek Views * Chef’s Kitchen * Walk To Lighthouse
Creek Views * Chef’s Kitchen * Walk To LighthouseSaugerties
9.8 out of 10, Exceptional, (7 reviews)
The price is ¥21,665
¥91,853 total
includes taxes & fees
Nov 15 - Nov 16

20. Cozy Catskill Escape
Cozy Catskill EscapeCatskill
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥22,689
¥43,676 total
includes taxes & fees
Nov 30 - Dec 1
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 Hillsdale Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
10/10 Excellent
Find out more about Hillsdale
Hillsdale Vacation Homes information
Number of reviews | 216 |
|---|---|
Accommodation | 629 Vacation Homes |
Lowest Price | ¥20,859 |
Highest Price | ¥189,740 |



































































