Holiday Rentals in Canaan

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Holiday Rentals in Canaan

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

9.8 out of 10, Exceptional, (10)
"Our stay at Villa Mariana was a great experience. The house was clean and comfortable and the location was perfect for our weekend plans. The check in and check out process was easy and our host was lovely to work with. She answered any questions we had and even had a nice snack waiting for us when we arrived!"
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Spacious 5-bedroom house in charming Lee with WiFi

The price is €735
includes taxes & fees
11 Aug - 12 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (20)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is €119
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (63)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (4)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (39)
"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!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"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

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

9.6 out of 10, Exceptional, (43)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA

10.0 out of 10, Exceptional, (1)
"The cabin is charming, rustic, and a perfect getaway for a birthday or romantic weekend trip.The pollinator garden is truly a delight, and I loved watching them in the morning. The garden has even motivated my partner and I to start one at home.I wish that the mosquitoes were not present as well, but they are to be expected during the summer in MA.Overall, the stay was amazing. Marci was super sweet and left some nice gifts for my birthday. I definitely want to have another stay here again!"
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (26)
"Great property for the fire and pool. Highly recommend for multiple families/couples. Close to town."
Peaceful Retreat Compound 10 Minutes to Great Barrington!

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (75)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Stay Lakeside This Summer!

Renovated Lakefront House w/ Dock: Pets Welcome!

9.0 out of 10, Wonderful, (20)
"the lake house is terrific and having the boats and a fire pit was such a nice thing."
Renovated Lakefront House w/ Dock: Pets Welcome!

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here. Location was excellent. Very peaceful and quiet. The house was clean and had everything you needed. Would come again!"
The price is €508
includes taxes & fees
10 Aug - 11 Aug
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (3)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

Rustic 3bd Lake Front Country Cottage

9.2 out of 10, Wonderful, (5)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage

Beautiful retreat in a lake community to the enjoy the summer season.

10.0 out of 10, Exceptional, (40)
"Great house in the woods. We were there for a spotting event so didn't spend a lot of time at the house. There were great walks around there"
Beautiful retreat in a lake community to the enjoy the summer season.
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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Top Canaan Hotel Reviews

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?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Canaan offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

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 Campbell Falls State Park and North Canaan Town Hall.

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.