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Canaan Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Canaan

Exterior
Cozy cabin in tranquil Canaan NY with WiFi, AC

Cozy cabin in tranquil Canaan NY with WiFi, AC

Canaan
Cozy cabin in tranquil Canaan NY with WiFi, AC
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2134)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is HK$747
HK$920 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (985)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
The price is HK$1,123
HK$1,255 total
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,469
HK$1,641 total
includes taxes & fees
15 Dec - 16 Dec
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is HK$1,010
HK$1,131 total
includes taxes & fees
17 Nov - 18 Nov
Micosta Leisure Inn
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is HK$971
HK$1,423 total
includes taxes & fees
17 Nov - 18 Nov
Taborton Harvest Boulder Pines Cabin in the woods
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,574
HK$2,313 total
includes taxes & fees
24 Nov - 25 Nov
Pet Friendly Riverfront Home in Great Barrington
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

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

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$2,972
HK$5,776 total
includes taxes & fees
21 Nov - 22 Nov
Spacious 5-bedroom house in charming Lee with WiFi
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"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...
United States
John O.
The price is HK$1,204
HK$2,501 total
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom Cabin for nature lovers
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is HK$4,655
HK$8,634 total
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak
Exterior
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham
9.6 out of 10, Exceptional, (93)
"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"
United States
Daisy H.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"We had a wonderful time with family and friends. The location was great and it was helpful for everyone to have their own bathroom. Kitchen was well stocked and toys for kids was a bonus."
United States
Erin B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

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

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
The price is HK$2,502
HK$5,632 total
includes taxes & fees
16 Nov - 17 Nov
Comfortable Berkshires retreat on mtn resort, SISO
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

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

Lee
9.4 out of 10, Exceptional, (71)
"Liked the 3 room suite, and 100 year old oak interior and the front porch, esp. as time went on. Walk to many restaurants, some only open in Fall after Wednesday. Some of the old doors fit like old doors, not unexpected, and felt like home away from home as time went on. Liked Fridge, coffee maker and small kitchen that we hardly used, but would have used more if longer stay."
United States
Leonard
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great stay!"
Ann 1-night trip
Posted 11 hours ago
The Yankee, Trademark Collection by Wyndham

Find out more about Canaan

Search for holiday rentals in Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in Canaan using one of the methods below:

  • View our selection of featured holiday rentals in Canaan
  • Use the map to find apartments and other holiday homes in the Canaan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Canaan while they last

Look no further and take a look at our great range of rental properties in Canaan!

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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This holiday home rental outside of Canaan offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a fridge, a stovetop and a coffee maker, so that you can cook with friends or family. You can relax into your holiday with a garden and table football.

How many holiday rentals are there in Canaan?

Choose from 13 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.