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Canaan Vacation Rentals

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Vacation Rentals in Canaan

Our top choices for Canaan vacation rentals

Cozy cabin in tranquil Canaan NY with WiFi, AC

Cozy cabin in tranquil Canaan NY with WiFi, AC

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1969)
"Beautiful location!"
$130 nightly
The price is $145
Aug 27 - Aug 28
Total with taxes and fees
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (967)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
$159 nightly
The price is $178
Sep 1 - Sep 2
Total with taxes and fees
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
$133 nightly
The price is $150
Aug 26 - Aug 27
Total with taxes and fees
Micosta Leisure Inn

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
$90 nightly
The price is $101
Sep 3 - Sep 4
Total with taxes and fees
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (126)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
$171 nightly
The price is $190
Aug 25 - Aug 26
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Spacious 5-bedroom house in charming Lee with WiFi

$714 nightly
The price is $798
Sep 2 - Sep 3
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
$968 nightly
The price is $1,046
Aug 26 - Aug 27
Total with taxes and fees
Hancock Village Inn at Jiminy Peak

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
$170 nightly
The price is $189
Aug 25 - Aug 26
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
$478 nightly
The price is $485
Aug 26 - Aug 27
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (166)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (88)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (86)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (26)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

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

9.4 out of 10, Exceptional, (64)
"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

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (15)
"House was very nice, spacious and updated. Property was secluded with a nice jacuzzi and fire pit area. "
Quintessential 6-BR Berkshires Lodge

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (124)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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

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?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This vacation home rental outside of Canaan offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.