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Compare 405 Vacation Homes in Williamstown with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (245)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is AED 551
AED 837 total
includes taxes & fees
13 May - 14 May
Berkshire Village Carriage House - Super Private!!

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (18)
"We absolutely loved this stay. The space was gorgeous and cozy. Fully equipped kitchen we were able to cook dinner in. The location about 45 minutes from Stratton where we skied, but was well worth the drive. Would absolutely stay here again. Thanks again Laurie! "
The price is AED 404
AED 954 total
includes taxes & fees
13 May - 14 May
Peaceful Stay at Birds of a Feather Farm & Spa

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
12 May - 13 May
Hancock Village Inn at Jiminy Peak

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (220)
"This property is absolutely gorgeous inside and out! It is very secluded with beautiful grounds, the inside is bigger than I was expecting and perfectly decorated to give off the secluded mountain cabin vibe, plus the wood stove is perfect. Lars was extremely nice and easy to communicate with, we will definitely stay again!"
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (71)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home

19th century school house converted into a charming two story dwelling

10.0 out of 10, Exceptional, (26)
"Beautiful, scenic location and great accommodations."
19th century school house converted into a charming two story dwelling

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat

Wilmington Vacation Rental Near Hiking and Skiing!

9.4 out of 10, Exceptional, (19)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (27)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (217)
"The owner was available through call/text, although we didn’t need anything. Beautiful house with even more beautiful views. The game room was a big hit. Hot tub and sauna were great as well. This house has everything! We will definitely be back!"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is AED 790
AED 1,921 total
includes taxes & fees
2 Jun - 3 Jun
2.5mi from the lake! Fire pit, arcade, yard games!
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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Other property types in Williamstown

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1804)
"The property was clean and the staff very accommodated."
The price is AED 403
AED 490 total
includes taxes & fees
12 May - 13 May
Vacation Village in the Berkshires

Huttopia Berkshires

1.0 star property
Huttopia Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 488
AED 545 total
includes taxes & fees
12 May - 13 May
Jiminy Peak Mountain Resort
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.