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Our top choices for The Berkshires vacation rentals

1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,255 reviews)
$114 nightly
The price is $128
Dec 5 - Dec 6
Total with taxes and fees

2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
8.8 out of 10, Excellent, (2,827 reviews)
$128 nightly
The price is $143
Nov 5 - Nov 6
Total with taxes and fees

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)
$320 nightly
The price is $357
Nov 5 - Nov 6
Total with taxes and fees

4. 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)
$365 nightly
The price is $407
Nov 10 - Nov 11
Total with taxes and fees

5. 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, (13 reviews)
$190 nightly
The price is $213
Nov 5 - Nov 6
Total with taxes and fees

6. 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)
$190 nightly
The price is $213
Nov 5 - Nov 6
Total with taxes and fees

7. 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)
$190 nightly
The price is $213
Nov 5 - Nov 6
Total with taxes and fees

8. 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)
$96 nightly
The price is $107
Nov 11 - Nov 12
Total with taxes and fees

9. Cozy Camper tucked into the woods
Cozy Camper tucked into the woodsSandisfield
10.0 out of 10, Exceptional, (1 review)
$156 nightly
The price is $174
Nov 5 - Nov 6
Total with taxes and fees

10. 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)
$273 nightly
The price is $305
Nov 5 - Nov 6
Total with taxes and fees

11. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (41 reviews)
$289 nightly
The price is $323
Nov 9 - Nov 10
Total with taxes and fees

12. 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)
$335 nightly
The price is $374
Nov 5 - Nov 6
Total with taxes and fees

13. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
$247 nightly
The price is $276
Nov 9 - Nov 10
Total with taxes and fees

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)
$190 nightly
The price is $213
Nov 5 - Nov 6
Total with taxes and fees

15. 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)
$190 nightly
The price is $213
Nov 5 - Nov 6
Total with taxes and fees

16. Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to ShopsWilliamstown
9.8 out of 10, Exceptional, (13 reviews)
$266 nightly
The price is $300
Nov 30 - Dec 1
Total with taxes and fees

17. 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)
$270 nightly
The price is $301
Nov 10 - Nov 11
Total with taxes and fees

18. 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)
$281 nightly
The price is $314
Nov 8 - Nov 9
Total with taxes and fees

19. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
$270 nightly
The price is $301
Nov 8 - Nov 9
Total with taxes and fees

20. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
$509 nightly
The price is $513
Nov 5 - Nov 6
Total with taxes and fees
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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