Canaan Vacation Rentals from ￥14,626: Search Short-Term Rentals

Q: What's the top vacation rental in Canaan?

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

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Vacation Rentals in Canaan

Enjoy a meal with a view from the kitchen, featuring a toaster, stainless steel dishwasher, and large window overlooking the surrounding landscape.

"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!"

Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

"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! "

Enjoy a serene lakeside view from this outdoor space with a wooden deck and glass door.

"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."

Guest rooms lead to a covered walkway with a tiled floor.

"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "

￥19,637 total

includes taxes & fees

Sep 1 - Sep 2

5 bedrooms, iron/ironing board, WiFi, bed sheets

￥116,839 total

includes taxes & fees

Aug 18 - Aug 19

Relax in this cabin's open-plan living area with a fireplace, scenic lake views, and comfortable seating.

"We had a great time. The owner Bill was a great host."

Escape to a serene lakeside retreat surrounded by trees and a tranquil atmosphere.

"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. "

Relax on the inviting porch with a comfortable sofa and armchairs, surrounded by a lush lawn and a charming house.

"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and large window offering a view of the outdoors.

"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"

"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!"

Stroll through the lush garden, surrounded by vibrant greenery and colorful flowers, to a serene outdoor space with a wooden fence and inviting bench.

"Even with horrible weather, we had a wonderful stay!"

Enjoy a serene lakeside view from the comfort of your room, surrounded by a tranquil forest and natural beauty.

"Great place! Loved waking up to a water view. Very peaceful."

Relax in this serene room with a large bed, stone fireplace, and forest views.

"We had a wonderful stay. The cabin was clean and comfortable! "

"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!"

Enjoy cooking in this well-equipped kitchen with a central island, oven, and ample workspace.

"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."

Escape to a serene forest retreat, where a peaceful gazebo awaits at the end of a winding staircase.

"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. "

Enjoy serene waterfront views from the spacious deck with lounge chairs and dining table.

"the lake house is terrific and having the boats and a fire pit was such a nice thing."

Enjoy al fresco dining and socializing on this tranquil outdoor deck, complete with a barbecue grill and comfortable seating.

"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!"

￥57,923 total

includes taxes & fees

Sep 3 - Sep 4

Enjoy meals in this charming dining area with a wooden table, white chairs, and a vase with sunflowers.

"We loved staying here! Great location!"

Relax by the clear pool surrounded by lounge chairs and lush greenery.

"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."

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Top Canaan Hotel Reviews

Quality Inn

10/10 Excellent

"I like that it is clean, quiet and convenient. The staff is very nice and helpful."

Monument Mountain Motel

10/10 Excellent

"This was one of the best motels I've stayed in. Normally motels are older and musty. This was very bright, no smell. White bathroom was very clean. Comfortable bed. It's set a little back on the main road. Because it was cool, we turned off the AC and opened the rear window. It was quiet. Check in/out was easy. Reasonable for the area. Highly recommend."

Find out more about Canaan

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Frequently asked questions

Are there vacation rentals in Canaan?

Yes, there are vacation rentals close to the most popular local attractions 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 coffeehouses.

What's the top vacation rental in Canaan?

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

How many vacation rentals are there in Canaan?

Expedia has 5 vacation 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 vacation rental in Canaan like?

Vacation rentals are private properties you can stay in for a long or short time in Canaan. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.

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Canaan Vacation Rentals

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Vacation Rentals in Canaan

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

Peace and quiet on the lake

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

Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

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

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

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

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

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

Cozy 2-bedroom Cottage with Access to Bantam Lake

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

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

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

Exclusive Estate, Heated Yearround Outdoor Pool

Stay Lakeside This Summer!

Renovated Lakefront House w/ Dock: Pets Welcome!

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

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

The Race Mountain House

Top Canaan Hotel Reviews

Quality Inn

Econo Lodge Lee - Great Barrington

Blackberry River Inn

Quality Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Days Inn by Wyndham Torrington

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Monument Mountain Motel

Find out more about Canaan

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Frequently asked questions