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Canaan Vacation Rentals

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Jul 13 - Jul 14
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Vacation Rentals in Canaan

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Relax on the covered porch with two comfortable rocking chairs overlooking a serene grassy area surrounded by trees.

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is ￥42,018
￥81,189 total
includes taxes & fees
Jul 16 - Jul 17
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is ￥85,657
￥146,895 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 5-bedroom house in charming Lee with WiFi
Berkshire Village Carriage House - Super Private!!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample seating for two.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
The price is ￥29,486
￥43,145 total
includes taxes & fees
Jul 31 - Aug 1
Berkshire Village Carriage House - Super Private!!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a window with a view.

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is ￥58,825
￥97,655 total
includes taxes & fees
Aug 4 - Aug 5
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Experience Timeless Elegance in The Edith Wharton Room!
Cozy retreat with a large bed, dresser, desk, and TV.

Experience Timeless Elegance in The Edith Wharton Room!

The price is ￥47,974
￥67,091 total
includes taxes & fees
Aug 11 - Aug 12
Experience Timeless Elegance in The Edith Wharton Room!
Cozy Carriage House room with a double bed and private balcony
Cozy retreat with a neatly made bed, bedside table, and elegant mirror.

Cozy Carriage House room with a double bed and private balcony

The price is ￥40,897
￥58,033 total
includes taxes & fees
Jul 14 - Jul 15
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Step outside to a serene outdoor space with a deck, Adirondack chairs, and a charming playhouse.

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is ￥55,050
￥76,147 total
includes taxes & fees
Aug 11 - Aug 12
Historic Susan B. Anthony Room - Cozy & Charming Stay
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Relax in a serene bedroom with a tufted headboard, desk, and dresser, perfect for work and rest.

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Elegant suite with a king bed, fireplace, and kitchenette.
Relax in this stylish living room with a large coffee table, two sofas, and a fireplace.

Elegant suite with a king bed, fireplace, and kitchenette.

The price is ￥58,589
￥80,594 total
includes taxes & fees
Jul 21 - Jul 22
Elegant suite with a king bed, fireplace, and kitchenette.
Elegant Carriage House room with a queen bed and private patio.
Cozy retreat with a large bed, dresser, and table, set amidst classic floral wallpaper and a decorative ceiling.

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Cheerful 3-bedroom cottage with woodstove
Relax in a serene outdoor space surrounded by lush greenery, featuring a wicker sofa set and a coffee table.

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is ￥39,364
￥79,211 total
includes taxes & fees
Jul 31 - Aug 1
Cheerful 3-bedroom cottage with woodstove
Home in Great Barrington
Enjoy cooking in this well-lit kitchen with a large window offering a view of the outdoors.

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is ￥40,838
￥61,425 total
includes taxes & fees
Aug 6 - Aug 7
Home in Great Barrington
Great Barrington Get Away
Enjoy cooking in this kitchen with stainless steel appliances, a large window offering a view of the outdoors, and a convenient trash can.

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is ￥66,344
￥108,195 total
includes taxes & fees
Jul 16 - Jul 17
Great Barrington Get Away
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Relax by the large pool in our outdoor space.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (70)
"We had a wonderful stay, thank you! "
The price is ￥38,627
￥81,022 total
includes taxes & fees
Jul 14 - Jul 15
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable Berkshires retreat on mtn resort, SISO
Relax by the pool surrounded by lush views and shaded lounge areas.

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is ￥30,665
￥79,537 total
includes taxes & fees
Jul 21 - Jul 22
Comfortable Berkshires retreat on mtn resort, SISO
Hancock Village Inn at Jiminy Peak
Charming two-story house with a historic facade, featuring a prominent address and star symbol, set amidst a serene winter landscape.

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is ￥88,163
￥162,145 total
includes taxes & fees
Jul 28 - Jul 29
Hancock Village Inn at Jiminy Peak
Near Tanglewood: Historic Summer Retreat
Enjoy cooking in this well-equipped kitchen with a stove, oven, refrigerator, coffee maker, and knife block.

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is ￥39,659
￥77,224 total
includes taxes & fees
Jul 14 - Jul 15
Near Tanglewood: Historic Summer Retreat
NEW RENO Historic Creamery in Berkshires w/hot tub
Relax in a spacious outdoor living area with a comfortable sofa set and sheltered seating options.

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (1)
"We used all amenities (besides hot tub) full kitchen and only brought food which worked well."
The price is ￥30,076
￥70,431 total
includes taxes & fees
Jul 14 - Jul 15
NEW RENO Historic Creamery in Berkshires w/hot tub
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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Frequently asked questions

Can I find vacation rentals in Canaan?

Yes, there are vacation rentals near popular points of interest in Canaan, or you can select a more secluded option if you want a relaxing place to stay. Canaan is known for its restaurants and coffeehouses. Make sure you have time to check out the shopping and local tours during your trip.

What's the top vacation rental in Canaan?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This vacation home rental outside of Canaan is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Canaan?

Choose from 16 Expedia vacation rentals in Canaan for a memorable vacation.

What’s there to see and do in Canaan?

Queechy Lake and Hollow FIelds Reserve are a couple of lovely local spots to get outside and enjoy nature. Hand Hollow State Forest and Bates Memorial State Park are other places to visit while you're in town.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can book for several days or longer in Canaan. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.