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Compare 66 Cottages in East Canaan with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....
Aerial view
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Newly renovated cottage on the lake!
Beach
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (18)
"This cabin was perfect for a place to rest and refresh after hiking some of Litchfield area's trails. It was as described by the host and he was very easy to reach with questions. We recommend this cabin as well-located for all that Litchfield county has to offer. "
Newly renovated cottage on the lake!
Two Bedroom Cottage Close To Town
Exterior
Two Bedroom Cottage Close To Town
9.6 out of 10, Exceptional, (17)
"What a wonderful time we had in this beautiful cottage! The property is so idyllic and perfect for a country getaway. We couldn’t ask for more in this home & needed for nothing. The beds were comfortable and the decor was just beautiful! The property owners were so friendly and very presponsive to any questions we had. We were staying in the area because it is close to Lime Rock Park, where my son was racing. We will definitely be back to stay in this wonderful cottage! Thank you for opening...
Two Bedroom Cottage Close To Town
East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental | Studio | 1BA | 800 Sq Ft | Steps to Enter
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Idillic summer getaway in Litchfield Hills, CT.
Property grounds
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (12)
"The property was lovely and the property manager was very friendly and accommodating. The space was ample, beds were very comfortable, and the a/c kept us cool in the middle of a heat wave. Only issue was that the house had a very musty smell to it. Also, the coffee pot was filled with old coffee-apparently they forgot to clean it prior to our arrival. Otherwise a great stay!"
Idillic summer getaway in Litchfield Hills, CT.
Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (98)
"Great property, just as it looked in the images."
Quiet rustic cottage with shared lake access
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (11)
"Beautiful house with amazing views. Very clean, all brand new. Great location. We would rent it again. Had an amazing Labor Day weekend. Thank you!"
Fun Getaway Lakehouse in the Hudson Valley
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Interior
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Aerial view
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
8.4 out of 10, Very Good, (5)
"We had a lovely two weeks at the Pfeifer cottage. Everything was as promised. The location was quiet, but easy access to Great Barrington and Tanglewood. Two of our grandkids visited and they were in love with the spiral staircase! We way come back again someday."
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
The Blue Elm - A Historic Berkshire Cottage
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (5)
"Beautifully kept, quaint little space - perfect for a relaxing getaway with a small family/friend group or two couples. Very private even though it was in back of the owners' property. The space was thoughtfully arranged and had one of the most in-depth guides to the property and surrounding areas we've ever seen! Nick and Tiffany were great hosts - I would be surprised if they didn't work in hospitality. I would go back."
The price is SAR 938
SAR 1,764 total
includes taxes & fees
22 Oct - 23 Oct
The Blue Elm - A Historic Berkshire Cottage
Cozy cottage with kettle pond lake 2 minutes away. FYI - No air conditioning!
Exterior
Cozy cottage with kettle pond lake 2 minutes away. FYI - No air conditioning!
9.0 out of 10, Wonderful, (2)
"This is a lovely property in a perfect, serene location. Highly recommend!"
Cozy cottage with kettle pond lake 2 minutes away. FYI - No air conditioning!
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Main deck
The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Relax on the large deck with lake views
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Peaceful Goshen Cottage w/ Screened Porch & Views!
Goshen Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required for Entry
Peaceful Goshen Cottage w/ Screened Porch & Views!
9.0 out of 10, Wonderful, (28)
"This is the second time our group has stayed at this lovely cottage. It has everything we need and the location is just minutes from the fairgrounds where we attended the folk festival. Initially we missed the posted WiFi password, and had outdated details on the Apple TV, but this was addressed."
Peaceful Goshen Cottage w/ Screened Porch & Views!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Tranquility/Fishermans Delight
Upper deck view
Lakefront Tranquility/Fishermans Delight
9.8 out of 10, Exceptional, (17)
"Accommodations good for Up to the 3 that rotated Total of 7 competed.Dock was perfect for the 3 kayaks and one 12 ft Al boat.Food prep was easy for Poppa [89] Cool mornings but the portable heaters took the chill off. weather was good couple windy 4 fish caught. Going to have to try again."
Lakefront Tranquility/Fishermans Delight
Beautiful Berkshires Cottage on Lake Buel
Great Barrington Vacation Rental | 3BR | 2.5BA | 2,000 Sq Ft | Steps Required
Beautiful Berkshires Cottage on Lake Buel
10.0 out of 10, Exceptional, (1)
"I’ve been visiting the Berkshires for decades and never stayed at a place with such an amazing view of Lake Buel! Sunrise right from my bed. The house was stocked with everything that was needed for an amazing weekend. Wonderful place to stay!"
Beautiful Berkshires Cottage on Lake Buel
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
New Marlborough Vacation Rental | 1BR | 1BA | 750 Sq Ft | Stairs Required
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (35)
"Quiet apot even when boaters were using the lake. Had a couple of issues that were addressed quickly."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior
A Charming Cottage - Secluded in Nature and Relaxing
10.0 out of 10, Exceptional, (2)
"I’ve been dreaming of a NYC getaway for years and fell in love with this home!!! I love the cozy feeling of being in such magical woods with such a beautiful lake nearby. Having access to the teepee was so special and added even more character. The beds are soooo comfortable I can’t wait to go back!!!"
A Charming Cottage - Secluded in Nature and Relaxing
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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 East Canaan

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (36)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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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