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

Vacation Rentals in Berkshire County

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Our top choices for Berkshire County vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is ￥15,036
￥20,346 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,556 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
The price is ￥13,807
￥17,166 total
includes taxes & fees
Aug 31 - Sep 1
Vacation Village in the Berkshires
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

3. 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.
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

4. 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, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is ￥20,743
￥51,932 total
includes taxes & fees
Aug 31 - Sep 1
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

5. 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, (39 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is ￥38,053
￥82,809 total
includes taxes & fees
Aug 24 - Aug 25
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

6. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ￥84,244
￥148,430 total
includes taxes & fees
Sep 21 - Sep 22
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

7. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,917
￥64,982 total
includes taxes & fees
Aug 24 - Aug 25
Home in Great Barrington
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

8. 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 ￥17,882
￥38,971 total
includes taxes & fees
Aug 25 - Aug 26
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

9. 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 ￥17,882
￥38,971 total
includes taxes & fees
Aug 25 - Aug 26
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

10. 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)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is ￥89,982
￥211,123 total
includes taxes & fees
Aug 25 - Aug 26
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

11. 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.
The price is ￥46,135
￥95,611 total
includes taxes & fees
Sep 22 - Sep 23
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 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, (77 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 ￥44,776
￥91,383 total
includes taxes & fees
Aug 24 - Aug 25
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

13. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (9 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is ￥21,458
￥47,031 total
includes taxes & fees
Aug 24 - Aug 25
Downtown | Waterfront | Walk to Shops
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
The price is ￥29,596
￥57,026 total
includes taxes & fees
Sep 22 - Sep 23
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

15. 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 Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥17,024
￥37,835 total
includes taxes & fees
Aug 24 - Aug 25
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

16. 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 ￥15,307
￥35,564 total
includes taxes & fees
Aug 24 - Aug 25
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

17. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is ￥20,664
￥45,050 total
includes taxes & fees
Aug 26 - Aug 27
New Studio In Town, By the Water
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

18. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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 ￥32,187
￥49,980 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Riverside Berkshires Retreat
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

19. 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 ￥99,972
￥182,631 total
includes taxes & fees
Sep 9 - Sep 10
Hancock Village Inn Near Jiminy Peak
A wooden deck with a table and chairs, surrounded by a white railing.

20. 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, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is ￥49,926
￥88,080 total
includes taxes & fees
Aug 24 - Aug 25
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Lovely setting. Comfortable and well equipped townhouse. We are not much for the pool or mini golf type “activities” but we like the location near biking, hiking, theater and dance venues. And the ability to have meals in instead of using restaurants every meal. Looks like a great place for family vacations."
barbara 2-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

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Vacation Apartments in Berkshire County

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