- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for The Berkshires vacation rentals

1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,259 reviews)
$107 nightly
The price is $119
Dec 8 - Dec 9
Total with taxes and fees

2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
8.8 out of 10, Excellent, (2,837 reviews)
$122 nightly
The price is $136
Dec 8 - Dec 9
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)
$311 nightly
The price is $347
Nov 9 - Nov 10
Total with taxes and fees

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)
$185 nightly
The price is $207
Nov 9 - Nov 10
Total with taxes and fees

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)
$185 nightly
The price is $207
Nov 9 - Nov 10
Total with taxes and fees

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, (13 reviews)
$185 nightly
The price is $207
Nov 9 - Nov 10
Total with taxes and fees

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)
$102 nightly
The price is $113
Nov 15 - Nov 16
Total with taxes and fees

8. Cozy Camper tucked into the woods
Cozy Camper tucked into the woodsSandisfield
10.0 out of 10, Exceptional, (1 review)
$152 nightly
The price is $170
Nov 9 - Nov 10
Total with taxes and fees

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)
$350 nightly
The price is $391
Nov 9 - Nov 10
Total with taxes and fees

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)
$326 nightly
The price is $364
Nov 9 - Nov 10
Total with taxes and fees

11. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
$281 nightly
The price is $314
Nov 9 - Nov 10
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)
$283 nightly
The price is $316
Nov 9 - Nov 10
Total with taxes and fees

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)
$185 nightly
The price is $207
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)
$185 nightly
The price is $207
Nov 9 - Nov 10
Total with taxes and fees

15. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
$262 nightly
The price is $292
Nov 9 - Nov 10
Total with taxes and fees

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)
$258 nightly
The price is $288
Nov 9 - Nov 10
Total with taxes and fees

17. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
$250 nightly
The price is $279
Nov 12 - Nov 13
Total with taxes and fees

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)
$262 nightly
The price is $292
Nov 10 - Nov 11
Total with taxes and fees

19. Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to ShopsWilliamstown
9.8 out of 10, Exceptional, (13 reviews)
$264 nightly
The price is $298
Nov 15 - Nov 16
Total with taxes and fees

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)
$257 nightly
The price is $287
Nov 9 - Nov 10
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.
Find vacation rentals that suit your style

Cabins

Apartments

































































































































