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Compare 92 Cottages in Canaan with updated reviews, rates, and availability.

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (13)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (23)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
Cozy Berkshire cottage with fireplace.

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"Beautiful wrap-around porch. Views were wonderful. Had to use the pullout sofa, because the stairs to the loft was basically a stepladder and for us seniors, was a no go. It does need a microwave. We gave it a four star overall, but for a younger couple would be a five."
Perfect Vacation Get Away - Historical New Marlborough

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (105)
"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."
Charming historic cottage on scenic road to Mt. Greylock

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (103)
"I am originally from Western Mass, and was looking for a quiet get away for my fiancé and I for my birthday weekend. This more than fit the bill, we had many romantic nights in front of the fire (big y or tractor supply good for indoor wood). The cabin was delightful, quaint. And it was so quiet this time of year with no one else around us, which was just what I was looking for. Our hosts were great, made everything very easy for check in and check out and were easily valve through the App....
Quiet rustic cottage with shared lake access

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (14)
"Beautiful clean property. A lovely location. Exceeded expectations."
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

15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake

10.0 out of 10, Exceptional, (8)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake

Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD

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 :CATAMOUNT SKI/SNOW BOARD

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

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!

A Charming Cottage - Secluded in Nature and Relaxing

10.0 out of 10, Exceptional, (3)
"The rental was nice. It was convenient for viewing the fall foliage and just enjoying the countryside. "
A Charming Cottage - Secluded in Nature and Relaxing

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'

Underhill Cottage

Underhill Cottage

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
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

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is AED 689
AED 792 total
includes taxes & fees
26 Jan - 27 Jan
Vacation Village in the Berkshires

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

10.0 out of 10, Exceptional, (33)
"We had a wonderful stay for our mother’s birthday with her 4 children and 10 of her 12 grandchildren. There was plenty to do for everyone especially with a 75 year difference in ages!!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 833 total
includes taxes & fees
26 Jan - 27 Jan
Berkshire Village Carriage House - Super Private!!
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.

Frequently asked questions

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