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Compare 257 Vacation Homes in Weatogue with updated reviews, rates, and availability.

Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Main Level LR sliding doors to Front Deck lake view, open to the dining room.

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (35)
"Our family recently stayed at this incredible vacation rental to celebrate a grandparent’s birthday, and it was truly the perfect setting for a special gathering. With 6 adults and 6 children under the age of 7, finding a place that could comfortably accommodate all of us was no small task—but this property exceeded every expectation. The location was ideal, with easy accessibility for family members traveling from different parts of the country and a manageable drive from Hartford airport....
Beautiful Berkshire Farm House on 160+ Acres
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
A Grand property in Historic Stockbridge
The Taggart House

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (4)
"This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process! "
Hudson Valley and The Berkshires getaway
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Exterior

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
View from deck looking over our dock on a still day in last days of October.

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (147)
"Highly recommend this house. Wonderful location, plenty of beds for a group. Great communication with the host."
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AED 584
AED 1,221 total
includes taxes & fees
3 Jan - 4 January 2025
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Elegant 19th Century New England 2BR vacation rental at Garfield House
Exterior

Elegant 19th Century New England 2BR vacation rental at Garfield House

10.0 out of 10, Exceptional, (88)
"Pretty darn perfect but not quite as clean as last year. Maybe different crew?"
Elegant 19th Century New England 2BR vacation rental at Garfield House
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
the most gorgeous location on earth!

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

9.8 out of 10, Exceptional, (35)
"We had an incredible time at this beautiful property . Completed secluded , we were in our own private oasis . We had our small intimate wedding on the property , overlooking the water , and it was perfect . The house is clean and cozy . The layout of the house is really nice , and even with many people staying there you aren’t on top of each other . So many things to do outdoors here , we spent the majority of our time enjoying the outdoors , and you really feel like you’re on your own private...
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
Large Barn styled vacation home that fits groups with space to spare.
Property grounds

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Exterior

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (113)
"We had a lovely holiday in this truly beautiful dream home. Everything promised in the VRBO advertisement was a reality - from the fireplace, the 4 bedrooms, the ping pong table, the kitchen and the glorious view. We even had a dusting of snow making the trees glisten. Absolutely lovely. Our host was most attentive as well—checking in with us to be sure we understood the heating units and the fireplace. We really had an ideal stay! "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Minutes from downtown Great Barrington, Convenient location
Exterior

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (43)
"Lovely home in a great location which fit our needs well. It was in great condition and quite comfortable.Wish we had more time to enjoy as there is so much to do in the area."
Minutes from downtown Great Barrington, Convenient location
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Terrace/patio

Waterfront Escape +dock +kayaks +firepit +fireplace +games

9.8 out of 10, Exceptional, (10)
"This was one of the most-special and memorable experiences my wife and I have ever had with a VRBO property and Owner. I had recently received a devastating medical diagnosis causing us to think about forfeiting our stay for 3 nights. After not checking in the 1st night, we decided to call Frank and let him know why we had not checked in but that we changed our minds and wanted to come for the last 2 nights as we needed the solitude and peace that his property on the lake might provide us. He...
Waterfront Escape +dock +kayaks +firepit +fireplace +games
5 Minutes from Catamount Ski Area
Dining

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (19)
"Older house with lots of character. We were there during a hot and humid spell and the upstairs was on the stuffy side but we were able to open most of the windows and get decent ventilation. There is a mini-split with AC in the kitchen but we had a hard time getting it to cool most of the house. We were in the area for a concert at Tanglewood and it was an easy drive. Overall a great little spot just probably a more comfortable stay in the fall and winter."
5 Minutes from Catamount Ski Area
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Summer in The Berkshires

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

10.0 out of 10, Exceptional, (19)
"Amazing and lovely"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Open floor plan great for large groups

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (89)
"Chip and Kim are exceptional hosts, and we enjoy coming to this property every Thanksgiving to gather as a family. It meets all of our needs, and we love it!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
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 Weatogue

Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
Berkshires Cabin 2 Mi to Appalachian Trail!
Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
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.