Search the Best Cabins in Winchester

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Cabin Rentals in Winchester

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Enjoy a serene lakeside view from this outdoor space with a wooden deck and glass door.

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (20)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA
Outdoor dining

Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA

10.0 out of 10, Exceptional, (1)
"The cabin is charming, rustic, and a perfect getaway for a birthday or romantic weekend trip.The pollinator garden is truly a delight, and I loved watching them in the morning. The garden has even motivated my partner and I to start one at home.I wish that the mosquitoes were not present as well, but they are to be expected during the summer in MA.Overall, the stay was amazing. Marci was super sweet and left some nice gifts for my birthday. I definitely want to have another stay here again!"
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Exterior

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

10.0 out of 10, Exceptional, (4)
"This cabin is so cute we had a relaxing time , will return"
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
'The Mill River Cabin’ w/ Fireplace & River View!
Cozy space with a high ceiling, large windows, and a central wooden table.

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (41)
"We had a great time during our stay at the Mill Creek cabin! The views of the river couldn't be beat & we enjoyed spending time reading on the porch & watching the wildlife from the huge living room windows. We will definitely be back!"
'The Mill River Cabin’ w/ Fireplace & River View!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Relax in this serene room with a large bed, stone fireplace, and forest views.

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (44)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Relax on the deck with a cozy seating arrangement, featuring a gazebo and comfortable furniture.

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (9)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Guesthouse Cabin vacation rentals in Berkshire County
Cozy cabin interior with a high ceiling and wooden beams, featuring a central dining table and fireplace.

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (7)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
$720 nightly
The price is $804
Aug 11 - Aug 12
Total includes taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Romantic and Secluded Berkshire's Gem
Cozy cabin-style interior with a central island kitchen, open fireplace, and comfortable seating area.

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (14)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Cozy & Chic Cabin by the Lake, with access to private Beach!
Escape to a serene cabin surrounded by lush greenery and a charming porch.

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (31)
"Stayed with my teen daughters for a fall “Gilmore Girls” CT weekend. Location was perfect for exploring all the best CT towns nearby."
Cozy & Chic Cabin by the Lake, with access to private Beach!
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Cozy space with a fireplace, perfect for relaxation and reading, featuring a comfortable seating area and storage shelves.

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.8 out of 10, Exceptional, (13)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Luxe Log Cabin Minutes From Skiing, Hiking, & More
Cozy cabin with a large dining table and wicker chairs, offering a serene forest view.

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Luxe Log Cabin Minutes From Skiing, Hiking, & More
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Cozy cabin with a rustic interior, large windows, and a comfortable seating area.

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

8.4 out of 10, Very Good, (8)
"Lovely cottage. Very clean. Everything we needed. We had a great time!"
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Great Family Cabin in the woods on a lake.
Cozy cabin interior with a dining area, living room, and kitchen, featuring a large chimney and comfortable seating.

Great Family Cabin in the woods on a lake.

10.0 out of 10, Exceptional, (2)
"The cabin and lake were even better than we expected. The cabin is fully equipped with almost everything you can think of for a comfortable stay. The lake water is very clean and the surrounding forest is sustainably maintained. Doolittle Lake is a hidden gem."
Great Family Cabin in the woods on a lake.
Rustic escape on a pond with 7 acres in Colebrook, CT!
Cozy attic bedroom with a sloped ceiling, featuring a bed and a wooden dresser with a mirror.

Rustic escape on a pond with 7 acres in Colebrook, CT!

Rustic escape on a pond with 7 acres in Colebrook, CT!
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Kitchen features a microwave, oven, and refrigerator, with ample counter space and a window.

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

9.6 out of 10, Exceptional, (8)
"Loved our stay!!!!"
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Serene Acreage - Pond - Hiking Trails Nearby
Relax on the covered porch with Adirondack chairs and a wooden table amidst a serene natural setting.

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Nature Escape w/ Deck & Garden: 3 Mi to Kent Falls
TV, books, video library

Nature Escape w/ Deck & Garden: 3 Mi to Kent Falls

Nature Escape w/ Deck & Garden: 3 Mi to Kent Falls
Cabin in the woods w cedar Hot Tub + private pond
Relax on the deck with a soothing hot tub surrounded by lush greenery.

Cabin in the woods w cedar Hot Tub + private pond

Cabin in the woods w cedar Hot Tub + private pond
Fantastic cottage in the Berkshire Mountains
Enjoy cooking in this well-equipped kitchen with a central island, sink, stove, and oven, plus a refrigerator with a water dispenser.

Fantastic cottage in the Berkshire Mountains

10.0 out of 10, Exceptional, (1)
"This cabin is very well-maintained with all the amenities you could ask for... especially no cable TV, and the owner David is responsive and pleasant! It is the perfect place to unplug, unwind and reconnect with life, nature and whoever you're traveling with. The house is an easy 30 minutes to Tanglewood and 20 minutes to Great Barrington so there is plenty to see and do without feeling like always being in the car. We got takeout from a delicious Thai restaurant (Siam Square) in Great...
Fantastic cottage in the Berkshire Mountains
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 Winchester Hotel Reviews

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"C"
Donald 4-night trip
Posted 21 hours ago
The Farmington Inn & Suites