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Compare 82 Cottages in Canaan with updated reviews, rates, and availability.

Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
View from property
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (14)
"Visited a local winery, Distillary & Ice Cream shop! Ate at Salt Water Grille, Met up with extended family from Mass."
Newly renovated cottage on the lake!
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is $200
$413 total
includes taxes & fees
May 23 - May 24
The Blue Elm - A Historic Berkshire Cottage
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Fridge, microwave, oven, stovetop
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...
Quiet rustic cottage with shared lake access
Beach nearby, sun loungers, beach towels
The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (2)
"My husband and I recently enjoyed a weekend at the Cottage at Highland Lake and would highly recommend it. The host gave excellent detailed directions, check in was easy, and the cottage was clean and exactly as described with a fully remodeled upstairs. There is a small deck off the master bedroom and a really nice size deck off the first floor, both overlooking the lake. Best of all is the location. The cottage is right on the lake and has a dock. Overall just a perfect weekend escape!"
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Property grounds
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (8)
"This was an excellent stay in a perfect location to explore both the Hudson Valley and the Berkshires. Host communicated seamlessly, and house is precisely as described. Very spacious and furnished in a neutral tones, minimalist style. Would recommend."
Fun Getaway Lakehouse in the Hudson Valley
Dining
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (2)
"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
Property grounds
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (2)
"The house is very cozy with a well appointed kitchen and a beautiful view of the lake. We would like to go back some day. The host is very responsive and kind."
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Smart TV, fireplace, books
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful location. Lots of hiking nearby. Countless places, towns, attractions, etc. to check out. The house was better than the pictures suggest. We are already making plans to return in the Spring / Summer."
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
Interior
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
Fridge, microwave, oven, stovetop
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
Lake
Lakefront Tranquility/Fishermans Delight
9.8 out of 10, Exceptional, (14)
"The cabin was just what we needed to escape the hustle and bustle of work!! Just the right size to sit and relax by the water and enjoy an early morning or late evening canoe ride while the Eagle flew above us. Perfect spot for day hikes or day drinking at the wineries. Then enjoy a bonfire with a glass of wine and talk about all you did and what you want to do the next day!! Definitely recommend and will be back"
Lakefront Tranquility/Fishermans Delight
Desk, internet, bed sheets
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!
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is $150
$270 total
includes taxes & fees
May 20 - May 21
Perfect Vacation Get Away - Historical New Marlborough
Fridge, microwave, oven, stovetop
Two Bedroom Cottage Close To Town
9.2 out of 10, Wonderful, (11)
"Had a wonderful stay. Great location for our visit to my son’s school."
Two Bedroom Cottage Close To Town
Beach
Dainty New Preston Cottage w/ Dock & Lake Views!
9.0 out of 10, Wonderful, (32)
"Loved our time at this cozy cottage by the lake!! Beautiful views and great antique decor in the cottage!!"
Dainty New Preston Cottage w/ Dock & Lake Views!
Outdoor dining
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (32)
"Quaint cabin tucked away in the Berkshires. For those vacationing with a pet, be aware that on Labor Day weekend this neighborhood puts on a fireworks show right by this house. Also, there really is not any yard, just a small patio. Lots of great hiking in the area."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Fridge, microwave, stovetop, dishwasher
Peaceful Goshen Cottage w/ Screened Porch & Views!
9.0 out of 10, Wonderful, (27)
"House was just right for our needs . Very comfortable ,clean, and private. We were in the area for family weekend at Kent School, wish we had more time to spend at the home and enjoy the great outdoors with the fall foliage and the nice outdoor fireplace. would definitely stay here again.."
Peaceful Goshen Cottage w/ Screened Porch & Views!
Interior
Cottage Retreat - Historic Cottage Home w Home Gym
6.0 out of 10, (3)
"Door code invalid as relayed. Check in time not honored. Upon entry thermostat read 41degrees on a a damp cold day. Multiple diffusers, plug-ins did not offset the dirty diaper, blood stained sheet, & foul bathroom smell. Meager linen supply, lack of detergent, rodent bags rounded out this thoroughly unpleasant experience."
The price is $99
$330 total
includes taxes & fees
May 21 - May 22
Cottage Retreat - Historic Cottage Home w Home Gym
View from property
Cozy cottage with kettle pond lake 2 minutes away
Cozy cottage with kettle pond lake 2 minutes away
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See all available properties in Canaan
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.

Other property types in Canaan

Fridge, microwave, oven, stovetop
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
10.0 out of 10, Exceptional, (1)
"We absolutely loved the place! Tons of space, all new appliances, fire pit and the gorgeous master bathroom were all highlights of our stay. Super convenient location within a few minutes of the Stop and Shop as well as other stores. Andrea was very friendly and attentive. She was there to quickly answer any questions we had and made sure we had everything we needed. Highly recommend!"
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"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
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
"We rented the house to celebrate mom’s 70th birthday. We wanted a quiet, simple place where we could spend time together, visit, and spend time outdoors. That’s exactly what we got. We all fished and kayaked and enjoyed the peaceful scenery. Thank you."
Peace and quiet on the lake
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.

Canaan Cottages information

Number of reviews
272
Accommodation
82 Cottages
Lowest Price
$150
Highest Price
$200

Frequently asked questions

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How can I find cheap cottages in Canaan?
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What is there to do in Canaan near my cottage?
Canaan has enough experiences and activities to keep you amused for weeks (or months!), beginning with Mount Frissell. Land of Nod Vineyard and Winery, Haystack Mountain State Park and Mount Riga State Park are other impressive attractions. If you’re sticking around a while, Campbell Falls State Park and Dennis Hill State Park will round off your itinerary nicely.

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