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Compare 317 Vacation Homes in Williamstown with updated reviews, rates, and availability.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

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

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 962
AED 1,954 total
includes taxes & fees
24 Nov - 25 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Large lakeside yard and patio area

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (49)
"We had such a great time at this house with our family. We were able to check in early and the place was clean and packed full of supplies for us to use during our stay such as plates, napkins, shampoo/conditioner, hair dryer, coffee, etc.! We brought fishing rods and fished off the dock. We also used the kayaks to go out on the lake and it was so much fun! Anytime we messaged Michael and Beverly they responded within minutes! We were able to check out late and it was the easiest check out I’ve...
The price is AED 1,102
AED 1,877 total
includes taxes & fees
1 Dec - 2 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Secluded Family Home in Serene Stockbridge Woods
Living area

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (18)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 525
AED 812 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.6 out of 10, Exceptional, (40)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

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

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Fully stocked newly renovated Kitchen.

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

10.0 out of 10, Exceptional, (105)
"We really enjoyed our stay at Julie’s home. We will definitely to look to stay here again the next time we visit the area. Highly recommended! "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Outdoor spa tub

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

10.0 out of 10, Exceptional, (39)
"We had a group of nine and had a great time. There are so many wonderful features including a fully stocked kitchen, activities for kids and an awesome outdoor area to hang out and relax. Would highly recommend this house. "
The price is AED 951
AED 2,582 total
includes taxes & fees
16 Dec - 17 Dec
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
House Front. Covered Porches, Lots of sunshine Plenty of space.

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

10.0 out of 10, Exceptional, (209)
"Clean and well supplied with fantastic views and close proximity to town.....a wonderful fall New England experience! "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (36)
"Fun girl’s weekend in the Berkshires! We will be back! Loved the rental and had lots of space! Beds were comfy and we had a great time. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Expansive Upstate Home w/ Home Theater!
East Schodack Vacation Rental | 5BR | 2.5BA | Stairs Required To Access

Expansive Upstate Home w/ Home Theater!

10.0 out of 10, Exceptional, (12)
"Owner was very responsive. House was spacious with everything we could have needed. Back yard and theater was amazing. 10 out of 10 recommend"
Expansive Upstate Home w/ Home Theater!
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Wonderful place to gather!

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

10.0 out of 10, Exceptional, (125)
"We enjoyed living in this beautiful house and spent an amazing vacation! The club house is also great with all the facilities!"
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
the house

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (33)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Exterior

SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails

10.0 out of 10, Exceptional, (5)
"We did have a team member slip and fall on the bottom step. He was just bruised up but a safety tread might not be a bad idea"
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Victorian Home in Bennington, Vermont
Front Porch

Victorian Home in Bennington, Vermont

10.0 out of 10, Exceptional, (86)
"The home is spacious, clean, bright, nicely decorated and well-equipped. An easy walk to shops and restaurants. It was great for our annual family gathering in southwestern Vermont."
Victorian Home in Bennington, Vermont
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Cozy living room nestled between the oversized kitchen and four-season porch.

4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee

9.6 out of 10, Exceptional, (5)
"This house had everything one could need for a quick getaway or longer stay. It was very comfortable and situated conveniently to Lee, Lenox and Stockbridge. We spent 3 days exploring and found many things to do. I expect to return and we would rent this house again in a heartbeat."
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Sunroom

Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!

10.0 out of 10, Exceptional, (2)
"Delightful property, worked well for our needs"
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Room

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (39)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is AED 620
AED 717 total
includes taxes & fees
24 Nov - 25 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 547
AED 600 total
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

9.6 out of 10, Exceptional, (54)
"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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.