Holiday Rentals in Canaan

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Holiday Rentals in Canaan

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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!

9.4 out of 10, Exceptional, (23)
"The host was great with communication! The is such a cute little place but the layout is very nice and everything was updated and very nice! Would book again!! "
The price is €368
includes taxes & fees
20 Feb - 21 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (16)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
The price is €2,402
includes taxes & fees
19 Feb - 20 Feb
Private Estate, Heated Yearround Outdoor Pool

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is €249
includes taxes & fees
22 Feb - 23 Feb
Litchfield Hills Hideaway

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

Peace and quiet on the lake

9.6 out of 10, Exceptional, (209)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Lakefront Winter Winderland in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (65)
"We had a beautiful, peaceful, cozy fall weekend at this cabin. The location is stunning next to the lake and across the street from hiking trails. The cabin had everything we needed and was quite comfortable. The only caveat is that it abuts a road with aggressive drivers so I did not feel comfortablet letting my dog off leash. Other than that, ideal. I will definitely be back! "
Lakefront Winter Winderland in New England Just 2 Hours From NYC

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....

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (22)
"This home is located in a beautiful area with plenty of nature surrounding. The amenities included are incredible. A large group of us visited and had so much fun on the pickle ball courts, hanging around the bonfire, and relaxing with the sauna and hot tub. This place can’t be beat!!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (44)
"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

10.0 out of 10, Exceptional, (138)
"We were a group of 9 girls visiting in the winter for a secluded getaway. We wanted to rest and relax after the holidays. The house was very large and accommodated our entire party comfortably. Notably, the house is not your typical bare bones vacation property. For example, the beds were comfortable and had real pillows. It is clearly used by the owners and well-loved. We hired chefs for all of our meals and the kitchen had everything we needed. I would definitely recommend this property for...
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (12)
"I want to preface my review by stating we had a wonderful time. We needed a getaway to unplug and relax and we were able to do just that. The area was beautiful, nature-plenty, quiet, secluded. There were a few unexpected glitches but nothing that we couldn't improvise around. Having said that, the listing said queen size beds, but they were only full, so my husband and I stayed in separate rooms which was sad . We also felt the people that prepped the home for our stay, must have ran short of...
Tolland Cabin w/ Private Hot Tub & Grill!

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (96)
"We had an amazing time. We had several out of town guests who stayed at the home and then a birthday party with local guests in the ballroom. The ballroom is absolutely stunning. The chef enjoyed the kitchen. There was plenty of parking and a beautiful setting. I would stay again. "
A Grand property in Historic Stockbridge

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (46)
"Our family stayed here for a long weekend to do some skiing. The house was perfectly located a short drive from Catamount. The house was super clean and had everything we needed. Marianne was a lovely host providing us with info before our check in and being available if we needed anything (we were all set but the offer was so nice). My son loved that there were some board games to choose from too! Would definitely recommend this property "
Minutes from downtown Great Barrington, Convenient location

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (37)
"The house was great. Plenty of bedrooms to fit our party of 16 (mix of kids and adults). Very comfortable hang out spaces and places to play games. The barn with the basketball court was awesome also! We got a lot of use out of that. The house was clean and everything worked well except that the dishwasher was broken. That was unfortunate, but these things happen, and we made due. The owner said that it would be fixed in a week or so, so hopefully not an issue for anyone else. Owner was...
Beautiful Berkshire Farm House on 160+ 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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Other types of properties in Canaan you may be interested in

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

3.5 star property
9.0 out of 10, Wonderful, (595)
"It was a great little getaway from the city, service was great and helpful nothing to complain about this spot"
The price is €140
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1005)
"Charming and old fashioned. The staff were extremely friendly and professional. Definitely will be going back. "
The price is €172
includes taxes & fees
19 Feb - 20 Feb
The Red Lion Inn

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (472)
"A cozy quiet charming place to stay."
The price is €68
includes taxes & fees
3 Mar - 4 Mar
The Little Lion
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

Are there holiday rentals in Canaan?

Yes, there are holiday rentals close to the most popular sights in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffee shops.

What are some of the best holiday rentals that Canaan has to offer?

Peace and quiet on the lake: This holiday home rental outside of Canaan is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Canaan?

Expedia has 5 holiday rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Edith Scoville Memorial Sanctuary are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Douglas Library and C H Pease Museum.

What’s a holiday rental in Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canaan. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.