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Compare 79 Cottages in Canaan with updated reviews, rates, and availability.

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!

10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (102)
"This delightful cottage is exceptional in every regard - comfort, cleanliness, and location! And the hosts, Lindsey and Steven, are by far the best hosts in the Berkshires! "
Quiet rustic cottage with shared lake access

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!

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

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "
Cozy 2-bedroom Cottage with Access to Bantam Lake

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Stylish Pine Plains Home Near Parks & Hiking!

3.0 star property
Stylish Pine Plains Home Near Parks & Hiking!

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (6)
"This cottage was both architecturally interesting and exceptionally well maintained, unlike most of VBRO rental properties. The screened-in porch, king-sided bed, and master bathroom were incredibly comfortable. The host was very personable and helpful. The location was quiet, yet convenient to towns and sites in the Berkshire mountains. Highly recommended as an exceptional property. "
The price is SAR 751
SAR 1,560 total
includes taxes & fees
14 Dec - 15 Dec
The Blue Elm - A Historic Berkshire Cottage

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!

Two Bedroom Cottage Close To Town

9.4 out of 10, Exceptional, (19)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town

Dainty New Preston Cottage w/ Dock & Lake Views!

9.0 out of 10, Wonderful, (33)
"We were in need of a nice, relaxing vacation and that’s exactly what we got. There were four of us (me, my husband, my 16-year-old, and my 11-year-old) and we each had our own space. We loved going down to the dock, and there is also a town beach just down the road. The home is filled with fun antiques and reminds you of a clean, well-kept, and charming grandmother’s house. We wanted a low-key vacation, and so we enjoyed short jaunts (less than 15 mins away) to Kent to enjoy its downtown and...
Dainty New Preston Cottage w/ Dock & Lake Views!

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (13)
"Nicely done lake house. Clean and spacious. Fire pit was a nice addition. Great communication with the host. The location was perfect for our needs. "
Fun Getaway Lakehouse in the Hudson Valley

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!

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!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (18)
"The cabin was simple, clean, and cozy. A great place to slow down, and enjoy a simpler lifestyle with a beautiful view of the lake. We hope to return during the summer when we can enjoy the lake fully. "
Lakefront Tranquility/Fishermans Delight
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 Canaan

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

9.8 out of 10, Exceptional, (9)
"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

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
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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