A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Berkshire County Holiday Rentals

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Our top choices for Berkshire County holiday rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,034 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$785
HK$1,052 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
Lobby

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,489 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is HK$815
HK$997 total
includes taxes & fees
31 Aug - 1 Sept
Vacation Village in the Berkshires
Room

3. Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (13 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$946
HK$1,056 total
includes taxes & fees
23 Aug - 24 Aug
Huttopia Berkshires
Property grounds

4. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$1,722
HK$3,860 total
includes taxes & fees
2 Aug - 3 Aug
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Coffee/tea maker, fridge, microwave, oven

5. 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 Dalton
Dalton
9.8 out of 10, Exceptional, (29 reviews)
"Had a fantastic time at Cathy’s place. So clean and everything you need for a great stay. Hope to visit again ! "
United States
Susan M.
The price is HK$1,094
HK$2,641 total
includes taxes & fees
12 Aug - 13 Aug
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Gift shop

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 Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$1,114
HK$2,216 total
includes taxes & fees
3 Aug - 4 Aug
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Dining

7. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Pool

8. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is HK$1,680
HK$3,138 total
includes taxes & fees
3 Aug - 4 Aug
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Gift shop

9. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is HK$1,114
HK$2,216 total
includes taxes & fees
3 Aug - 4 Aug
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Interior

10. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,873
HK$2,837 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Riverside Berkshires Retreat
Pool

11. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is HK$2,372
HK$4,717 total
includes taxes & fees
3 Aug - 4 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Coffee/tea maker, fridge, microwave, oven

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$2,118
HK$3,206 total
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington
Interior

13. Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (13 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is HK$3,137
HK$5,484 total
includes taxes & fees
3 Aug - 4 Aug
Guesthouse Cabin vacation rentals in Berkshire County
Outdoor dining

14. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (17 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$980
HK$2,170 total
includes taxes & fees
2 Aug - 3 Aug
New Studio In Town, By the Water
Outdoor dining

15. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,463
HK$4,346 total
includes taxes & fees
3 Aug - 4 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

16. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$5,756
HK$10,062 total
includes taxes & fees
1 Sept - 2 Sept
Hancock Village Inn Near Jiminy Peak
Pool

17. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (5 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
The price is HK$1,715
HK$3,178 total
includes taxes & fees
3 Aug - 4 Aug
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Pool

18. 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 Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is HK$1,002
HK$2,075 total
includes taxes & fees
3 Aug - 4 Aug
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
TV, fireplace, printers

19. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,440
HK$10,417 total
includes taxes & fees
6 Aug - 7 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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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Top Berkshire County Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very clean and in a great location. Fun bar on property"
Mary 2-night trip
Posted 1 hour ago
Berkshires Untold