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Top Holiday Rentals in Canaan

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

10.0 out of 10, Exceptional, (11)
"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 Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT

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

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, (3)
"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 £102
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is £623
includes taxes & fees
18 Aug - 19 Aug
Spacious 5-bedroom house in charming Lee with WiFi

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

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

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

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, (5)
"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

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

9.6 out of 10, Exceptional, (44)
"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

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 £297
includes taxes & fees
3 Sept - 4 Sept
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 Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (40)
"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!

Becket Home w/ 3-Season Porch: Walk to Lake Access

2.0 star property
9.6 out of 10, Exceptional, (5)
"This was a clean, quiet spot for a nice weekend getaway. "
Becket Home w/ 3-Season Porch: Walk to Lake Access
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?

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 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.