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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 78 Cottages in 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....
Idillic summer getaway in Litchfield Hills, CT.
Property grounds

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.
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!
Two Bedroom Cottage Close To Town
Exterior

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
Cozy 2-bedroom Cottage with Access to Bantam Lake

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
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Living area

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
The Blue Elm - A Historic Berkshire Cottage
Bathroom

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is AED 735
AED 1,510 total
includes taxes & fees
24 Feb - 25 Feb
The Blue Elm - A Historic Berkshire Cottage
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!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Stockbridge Vacation Rental | 4BR | 2BA | 1,700 Sq Ft | 3 Steps to Enter

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Quiet rustic cottage with shared lake access

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
Dainty New Preston Cottage w/ Dock & Lake Views!
Preston Vacation Rental | 3BR | 2BA | 1,300 Sq Ft | Stairs Required

Dainty New Preston Cottage w/ Dock & Lake Views!

9.0 out of 10, Wonderful, (34)
"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!
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
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, (29)
"Enjoyed our stay very much. The accommodations suited our needs. Appreciated the cleanliness of the property and the ease of checking in/out."
Peaceful Goshen Cottage w/ Screened Porch & Views!
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, (15)
"Can't say enough about this place. It looked like it was just recently built or renovated, and was very very clean. The place was warm, inviting, and very comfortable for my family of 5. Leticia is amazing, very very responsive and understanding. If you are staying in the area (the lake, skiing, etc.) I would highly recommend this place. We will definitely look to book this place again the next time we go skiing at Catamount."
Fun Getaway Lakehouse in the Hudson Valley
Lakefront Tranquility/Fishermans Delight
Upper deck view

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
Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD
Relax on the large deck with lake views

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
Perfect Vacation Get Away - Historical New Marlborough
Exterior

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
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!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior

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
Family Cottage with Games, Fireplace. 5 min to Taghkanic Hiking, Hudson 20 min.
Living area

Family Cottage with Games, Fireplace. 5 min to Taghkanic Hiking, Hudson 20 min.

10.0 out of 10, Exceptional, (2)
"My family of four stayed at this house for a wedding in the area. The house was more than we expected. Very comfortable, good feel, and just an overall good experience."
Family Cottage with Games, Fireplace. 5 min to Taghkanic Hiking, Hudson 20 min.
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

Remodeled Lakefront retreat!! Come join us for Ski Season!!
Aerial view

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (23)
"This property is clean, updated and warm! We were up for a race at Catamount and this cottage was perfect for our weekend stay. The host, Robert, was quick to respond when contacted with a quick question and otherwise there were no issues. "
The price is AED 716
AED 1,387 total
includes taxes & fees
24 Feb - 25 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool
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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