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Canaan Holiday Rentals

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Holiday Rentals in Canaan

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, (1941)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is AU$202
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (959)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is AU$272
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (114)
"Beautiful grounds with the most gracious of hosts. Lovely accommodations! Will stop there again!"
The price is AU$223
includes taxes & fees
12 Aug - 13 Aug
Micosta Leisure Inn

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (2)
"Huttopia Berkshires was wonderful! Very peaceful and a beautiful view. We enjoyed the on-site coffee shop/cafe and our tent with a deck and indoor plumbing! The staff was extremely friendly and helpful. The pool is lovely. Highly recommend!"
The price is AU$168
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"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."
The price is AU$303
includes taxes & fees
12 Aug - 13 Aug
Taborton Harvest Boulder Pines Cabin in the woods

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,225
includes taxes & fees
18 Aug - 19 Aug
Spacious 5-bedroom house in charming Lee with WiFi

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."
The price is AU$301
includes taxes & fees
12 Aug - 13 Aug
Taborton Harvest Timber Trails Unique cabin experience

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is AU$1,722
includes taxes & fees
20 Aug - 21 Aug
Hancock Village Inn at Jiminy Peak

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

10.0 out of 10, Exceptional, (165)
"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

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

9.8 out of 10, Exceptional, (85)
"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!!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"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. "
The price is AU$207
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds

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

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

9.6 out of 10, Exceptional, (88)
"Our group had a great time. The place is a bit dated but has room for plenty of people."
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$750
includes taxes & fees
12 Aug - 13 Aug
Comfortable Berkshires retreat on mtn resort, SISO

Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
The price is AU$535
includes taxes & fees
9 Sept - 10 Sept
Charming 3-bedroom Cabin for nature lovers

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (48)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
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 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. Make sure you have time to check out the shopping and local tours during your trip.

What are some of the best holiday rentals that Canaan has to offer?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This holiday 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 holiday rentals are there in Canaan?

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

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 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 offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.