Holiday Homes in Weatogue

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Featured Holiday Homes in Weatogue

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.

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

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

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

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway

Serene Salisbury Rental Home on 26 Acres w/ Deck!

9.8 out of 10, Exceptional, (7)
"Great weekend getaway with family to celebrate "
Serene Salisbury Rental Home on 26 Acres w/ Deck!

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio

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 AU$575
includes taxes & fees
30 Nov - 1 Dec
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!

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

Cottage at Copake Lake

10.0 out of 10, Exceptional, (61)
"House was very clean and cozy. Has everything you need and we were very comfortable. Really peaceful location. Short walk to dock where they have paddle board, kayak and seating. Highly recommend if you’re looking for a place at Cooke lake."
Cottage at Copake Lake

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

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

10.0 out of 10, Exceptional, (18)
"The property was close to town and very cozy, clean & comfortable. Would highly recommend attention to the details was impressive."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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

10.0 out of 10, Exceptional, (89)
"My family and I loved our stay in Chip and Kim’s lovely post and beam home in Lee. The home was lovely and comfortable for our group of eight, ages two months to 70 years. The home is well-equipped, spacious and charming. Due to the nonstop rain, we were unable to enjoy the gorgeous grounds, but felt very cozy in the fireplaces living room. I highly recommend!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Sunsets On Blue Hill, Newly Renovated Farmhouse

10.0 out of 10, Exceptional, (1)
"The property was really beautiful. Well stocked, well designed and even better than the photos. The owners were incredibly responsive and accommodating. Couldn’t recommend this place more!"
Sunsets On Blue Hill, Newly Renovated Farmhouse

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (78)
"We had a wonderful stay here. The house is very spacious and was perfect for kids with enough spaces for everyone to sleep and run around. Jennifer was super responsive (within minutes) and friendly and we experienced no problems with the house. My only regret is not being able to spend as much time as we wanted at the house to utilize their amazing backyard (we we had a family wedding which took us away from the property each day). Highly recommend this place - especially to families with kids!"
Spacious Home nestled along the Blackberry River in Northwest CT

Catamount, Zip Line, Private Setting, Book Now!

10.0 out of 10, Exceptional, (5)
"This house was perfect for our group. It is spacious, modern and comfortable with a great yard and views of Catamount. We loved that the house is so new and clean yet also dog friendly. The proximity to the mountain made our ski days so easy. The kitchen is well equipped and we made dinner there several nights. One small gripe: firewood not supplied for the awesome stone fireplace. But we brought our own. Overall a wonderful house and we will be back."
Catamount, Zip Line, Private Setting, Book Now!

Renovated Lakefront House w/ Dock: Pets Welcome!

9.0 out of 10, Wonderful, (20)
"The house was perfectly situated on the lake. It had areas that I could close the gates, deck/yard, to keep in or out my 3yr old grandson and our dog. It made for a very relaxing time for all of us. The rooms were spacious and comfortable. There were plenty of toys to keep my grandson occupied! My 15 yr old granddaughter loved fishing off the deck and the dock. The host was very available and helpful. The grocery store was a short drive away! I will definatly book this house again next...
Renovated Lakefront House w/ Dock: Pets Welcome!

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (59)
"If ever in the area again, we will definitely stay at Bluebird Farmhouse. It is so charming with wonderful artwork throughout this warm and comfortable home. A beautiful setting with a very well equipped home providing everything you need. We were in town for a wedding and thoroughly enjoyed our stay at this special farmhouse!!"
Bluebird Valley Farmhouse
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

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
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.
Beautiful view of the beach with palm trees

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