Holiday Homes in Williamstown

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Featured Holiday Homes in Williamstown and around

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (70)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

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

10.0 out of 10, Exceptional, (128)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is €425
includes taxes & fees
26 Aug - 27 Aug
Comfortable Berkshires retreat on mtn resort, SISO

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.6 out of 10, Exceptional, (8)
"The house was clean, nicely decorated, comfortable and all the amenities we needed! "
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (7)
"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"
Mountain Sanctuary Dome Rustic Solitude 5BR

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

9.8 out of 10, Exceptional, (93)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is €320
includes taxes & fees
26 Aug - 27 Aug
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

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

10.0 out of 10, Exceptional, (132)
"This was our second time renting this property for a quick ski trip. The property is spacious, and well appointed. It really offers everything you need for a relaxing ski vacation. Love the game room and the space."
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (72)
"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!

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

10.0 out of 10, Exceptional, (52)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

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

10.0 out of 10, Exceptional, (24)
"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (13)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East

Walk to Dining: Downtown Lenox Guest House!

9.4 out of 10, Exceptional, (29)
"Great location and convenient walking distance to downtown Lenox. "
Walk to Dining: Downtown Lenox Guest House!

Spyglass village- Golf & Ski

10.0 out of 10, Exceptional, (3)
"Great location, close to Mount Snow, ideal for skiing. Property is newly renovated, very functional and well appointed. We really enjoyed our stay."
Spyglass village- Golf & Ski

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"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

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox

Idyllic Berkshires Farmhouse

Idyllic Berkshires Farmhouse

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!
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 Williamstown Hotel Reviews