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Our top choices for The Berkshires holiday rentals

1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
The price is NZ$192
includes taxes & fees
6 Dec - 7 Dec

2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
8.8 out of 10, Excellent, (2,840 reviews)
The price is NZ$179
includes taxes & fees
12 Nov - 13 Nov

3. 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 NZ$620
includes taxes & fees
19 Nov - 20 Nov

4. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone DecorHancock
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$373
includes taxes & fees
12 Nov - 13 Nov

5. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at MtnHancock
9.4 out of 10, Exceptional, (19 reviews)
The price is NZ$373
includes taxes & fees
12 Nov - 13 Nov

6. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn RedoneHancock
10.0 out of 10, Exceptional, (14 reviews)
The price is NZ$373
includes taxes & fees
12 Nov - 13 Nov

7. 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 NZ$205
includes taxes & fees
20 Nov - 21 Nov

8. Cozy Camper tucked into the woods
Cozy Camper tucked into the woodsSandisfield
10.0 out of 10, Exceptional, (1 review)
The price is NZ$311
includes taxes & fees
12 Nov - 13 Nov

9. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beautiful 2-Bedroom + Loft with Hot Tub at Lake AshmereHinsdale
9.8 out of 10, Exceptional, (41 reviews)
The price is NZ$697
includes taxes & fees
12 Nov - 13 Nov

10. 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 NZ$651
includes taxes & fees
17 Nov - 18 Nov

11. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is NZ$582
includes taxes & fees
15 Nov - 16 Nov

12. 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 NZ$530
includes taxes & fees
12 Nov - 13 Nov

13. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone DecorHancock
10.0 out of 10, Exceptional, (6 reviews)
The price is NZ$373
includes taxes & fees
12 Nov - 13 Nov

14. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country InnHancock
9.8 out of 10, Exceptional, (25 reviews)
The price is NZ$373
includes taxes & fees
12 Nov - 13 Nov

15. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is NZ$509
includes taxes & fees
13 Nov - 14 Nov

16. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - GorgeousHancock
9.6 out of 10, Exceptional, (35 reviews)
The price is NZ$522
includes taxes & fees
12 Nov - 13 Nov

17. 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 NZ$510
includes taxes & fees
16 Nov - 17 Nov

18. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming DaltonDalton
9.8 out of 10, Exceptional, (35 reviews)
The price is NZ$529
includes taxes & fees
12 Nov - 13 Nov

19. Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to ShopsWilliamstown
9.8 out of 10, Exceptional, (13 reviews)
The price is NZ$541
includes taxes & fees
15 Nov - 16 Nov

20. 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 NZ$520
includes taxes & fees
12 Nov - 13 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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