Our top choices for The Berkshires vacation rentals

1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
$107 nightly
The price is $119
Dec 13 - Dec 14
Total with taxes and fees

2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
8.8 out of 10, Excellent, (2,841 reviews)
$108 nightly
The price is $121
Nov 17 - Nov 18
Total with taxes and fees

3. 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 13 - Nov 14
Total with taxes and fees

4. 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)
$104 nightly
The price is $116
Nov 18 - Nov 19
Total with taxes and fees

5. 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 13 - Nov 14
Total with taxes and fees

6. 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 15 - Nov 16
Total with taxes and fees

7. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
$260 nightly
The price is $290
Nov 16 - Nov 17
Total with taxes and fees

8. 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)
$202 nightly
The price is $226
Nov 15 - Nov 16
Total with taxes and fees

9. 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)
$202 nightly
The price is $226
Nov 15 - Nov 16
Total with taxes and fees

10. 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)
$202 nightly
The price is $226
Nov 16 - Nov 17
Total with taxes and fees

11. 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)
$377 nightly
The price is $421
Nov 15 - Nov 16
Total with taxes and fees

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)
$290 nightly
The price is $324
Nov 15 - Nov 16
Total with taxes and fees

13. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
$270 nightly
The price is $302
Dec 13 - Dec 14
Total with taxes and fees

14. 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)
$202 nightly
The price is $226
Nov 15 - Nov 16
Total with taxes and fees

15. 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)
$202 nightly
The price is $226
Nov 15 - Nov 16
Total with taxes and fees

16. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
$257 nightly
The price is $287
Nov 13 - Nov 14
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 17 - Nov 18
Total with taxes and fees

18. 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)
$259 nightly
The price is $289
Nov 13 - Nov 14
Total with taxes and fees

19. Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to ShopsWilliamstown
9.8 out of 10, Exceptional, (13 reviews)
$270 nightly
The price is $304
Nov 15 - Nov 16
Total with taxes and fees

20. 2-Bdr Apt In Town, By the Water
2-Bdr Apt In Town, By the WaterWilliamstown
9.2 out of 10, Wonderful, (23 reviews)
$259 nightly
The price is $292
Nov 15 - Nov 16
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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