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Compare 401 Vacation Homes in Williamstown with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 855 total
includes taxes & fees
14 Apr - 15 Apr
Berkshire Village Carriage House - Super Private!!

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (17)
"Wonderful get away for the week in VT. Place was clean and beautiful, host was very helpful, and views were gorgeous! "
The price is SAR 413
SAR 975 total
includes taxes & fees
14 Apr - 15 Apr
Peaceful Stay at Birds of a Feather Farm & Spa

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,245
SAR 4,119 total
includes taxes & fees
15 Apr - 16 Apr
Hancock Village Inn at Jiminy Peak

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (220)
"had an amazing stay at this beautifully renovated barn in Vermont! The property is stunning, with several acres of land offering breathtaking mountain views. The barn itself is a perfect blend of rustic charm and modern comfort, with thoughtful details that made the stay extra special. I especially loved the walking trails right on the property—such a peaceful way to start and end the day. If you’re looking for a relaxing getaway surrounded by nature, this is the perfect spot. Highly recommend...
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)
"Great place with an elite game room. "
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, (70)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
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)
"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"
Mountain Blossom Retreat by Evergreen Home

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

10.0 out of 10, Exceptional, (24)
"Intentional home, not a cheap flip for rentals. Truly the most conscientious and thoughtful VRBO or rental home we have stayed at in over 13 years of regularly traveling. A central location for us to visit many communities we were interesting exploring what the hype was all about; NY City, The Berkshires/Lenox, MA, Catskills/Woodstock NY, Southern Vermont. Fantastic kitchen with all the cookware, utensils, and space we needed. Perfectly quiet, very peaceful, a loved historical home and land."
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, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
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)"
The price is SAR 488
SAR 1,314 total
includes taxes & fees
14 Apr - 15 Apr
Near Tanglewood: Historic Summer Retreat

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (19)
"We loved the feel of this rustic yet modern cabin. It had everything we needed and was the perfect getaway for us for a few nights of skiing at mount snow. The stairs and pathway to get down to the place are not ideal for older individuals with limited mobility as it can get slippery and we found the driveway very icy but that comes with the reality of living in New England. I just thought I would put this in here for those who are in their later years and have to consider their mobility. We are...
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)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
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)
"Would definetely stay again.IF....LOL minor but not so minor.Need t.v. in master bedroom.Would not be a huge iinvestment.Cc"
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)
"Ben and I enjoyed a good long weekend at the correctly described Beautiful Lenox Home. Mary, your host, has thought of everything to help you feel comfortable and very quickly to adjust to your home away from home. It is very well located so that you can easily visit the many places of interest nearby. The rules for checking in and out were clear and simple. We are delighted give this a 5-star rating. David and Ben will return, for sure!"
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, (215)
"We had a great long weekend with the family in this warm and comfortable house overlooking a beautiful lake. The place was spotless and well-appointed. The best mark of a good host is someone who goes above and beyond to make your visit"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (40)
"Cozy home with a cabin like feel. Plenty of room and warmth. The 3 bedrooms accommodated our group perfectly! Easy check in instructions"
Dancing Horse Lodge
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, (1796)
"The location to jimney peak was great."
The price is SAR 372
SAR 449 total
includes taxes & fees
23 Apr - 24 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (927)
"Staff was exceptionally helpful and friendly."
The price is SAR 503
SAR 562 total
includes taxes & fees
21 Apr - 22 Apr
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.