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Compare 78 Cottages in Williamstown with updated reviews, rates, and availability.

Charming historic cottage on scenic road to Mt. Greylock
Summer

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
Cozy cottage with pool, walking distance to lake
Private kitchen

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (13)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake
Cozy Berkshire cottage with fireplace.
Interior

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (23)
"We had a wonderful experience- house was clean and very comfy with all the amenities. Hosts went out of their way both before and during our stay to provide information and make sure all our needs were met! We enjoyed relaxing in the house and the location was also very close to many great Berkshires sights!! Highly recommend this listing! "
Cozy Berkshire cottage with fireplace.
Welcome to the Red Bridge Cottage!
Cozy cottage with glass door pellet stove & whirlpool tub for those snowy nights

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Skiing open now at Prospect Mountain Snowmobiling coming soon Book now before up

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (132)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Perfect for a peaceful get away in clean fresh Vermont air!
Newly sided entire house and garage

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (71)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
Livingroom - Woodburning stove and sleeper double size pull out couch.

Lake life at Woodford Cottage

9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake
Private kitchen

15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake

10.0 out of 10, Exceptional, (8)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake
Beachwood Cottage
Exterior detail

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Exterior

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Spacious Historic Home in the Berkshires!
Property grounds

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Charlemont Retreat on Chickley River w/ EV Charger
Living area

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Cottage in the Clouds With Mountain Views
Fully stocked kitchen. Two skylights provide plenty of natural light

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Living area

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Cozy Treetop Hideaway Near Harriman Reservoir!
Exterior

Cozy Treetop Hideaway Near Harriman Reservoir!

3.0 star property
Cozy Treetop Hideaway Near Harriman Reservoir!
Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Stockbridge Home: Walk to Town Beach!
Exterior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
'john's Farmhouse in Mount Snow' on 120 Acres!
Exterior

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!
Near Hiking & Skiing: Home in Wilmington!
Living area

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!
Wilmington Vacation Rental Near Hiking and Skiing!
Living area

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
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, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
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, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AED 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 551
AED 837 total
includes taxes & fees
1 Jan - 2 January 2025
Berkshire Village Carriage House - Super Private!!
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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