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Our top choices for Southfield holiday rentals

1. Cozy 1-bedroom studio in serene Great Barrington with AC
Cozy 1-bedroom studio in serene Great Barrington with ACGreat Barrington
8.8 out of 10, Excellent, (10 reviews)
The price is €105
includes taxes & fees
17 Nov - 18 Nov

2. Cozy Camper tucked into the woods
Cozy Camper tucked into the woodsSandisfield
10.0 out of 10, Exceptional, (1 review)
The price is €158
includes taxes & fees
18 Nov - 19 Nov

3. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is €369
includes taxes & fees
18 Nov - 19 Nov

4. 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 €260
includes taxes & fees
16 Nov - 17 Nov

5. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is €298
includes taxes & fees
15 Nov - 16 Nov

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, LakeGreat Barrington
10.0 out of 10, Exceptional, (7 reviews)
The price is €292
includes taxes & fees
15 Nov - 16 Nov

7. 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 €326
includes taxes & fees
12 Nov - 13 Nov

8. Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Enjoy a restful stay with fast internet, smart TV and the company of your pet.winsted
9.4 out of 10, Exceptional, (55 reviews)
The price is €186
includes taxes & fees
22 Nov - 23 Nov

9. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/DryerGreat Barrington
The price is €332
includes taxes & fees
20 Nov - 21 Nov

10. 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, (5 reviews)
The price is €172
includes taxes & fees
15 Nov - 16 Nov

11. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is €269
includes taxes & fees
12 Nov - 13 Nov

12. 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 €322
includes taxes & fees
18 Nov - 19 Nov

13. 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 €604
includes taxes & fees
16 Nov - 17 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 €265
includes taxes & fees
12 Nov - 13 Nov

15. 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

16. 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 €1,081
includes taxes & fees
21 Nov - 22 Nov

17. Ideal location for summer and winter activities with plenty of outdoor space.
Ideal location for summer and winter activities with plenty of outdoor space.Hillsdale
9.8 out of 10, Exceptional, (80 reviews)
The price is €311
includes taxes & fees
15 Nov - 16 Nov

18. 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 €557
includes taxes & fees
16 Nov - 17 Nov

19. The Brooks Motel: Exceptional Suite
The Brooks Motel: Exceptional SuiteHillsdale
7.2 out of 10, Good, (5 reviews)
The price is €191
includes taxes & fees
8 Dec - 9 Dec

20. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is €546
includes taxes & fees
21 Nov - 22 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.
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