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Canaan Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Canaan holiday rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2194)
"I great place to stay!!"
United Kingdom
Maricel
The price is HK$808
HK$988 total
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (134)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is HK$1,010
HK$1,131 total
includes taxes & fees
31 Dec - 1 Jan 2026
Micosta Leisure Inn
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,651
HK$1,845 total
includes taxes & fees
8 Jan - 9 Jan 2026
Jiminy Peak Mountain Resort
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$762
HK$1,028 total
includes taxes & fees
6 Jan - 7 Jan 2026
All comforts of home
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
The price is HK$1,049
HK$1,587 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Property grounds
All the comforts of home

Holiday Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$825
HK$1,098 total
includes taxes & fees
6 Jan - 7 Jan 2026
All the comforts of home
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Cabin in Sand Lake

Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is HK$971
HK$1,423 total
includes taxes & fees
31 Dec - 1 Jan 2026
Taborton Harvest Boulder Pines Cabin in the woods
Terrace/patio
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is HK$1,224
HK$2,851 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$956
HK$1,845 total
includes taxes & fees
5 Jan - 6 Jan 2026
Berkshires Apartment at the Stephentown Hotel
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

Mobile Home in Chatham

HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is HK$1,749
HK$3,208 total
includes taxes & fees
13 Jan - 14 Jan 2026
HunnyHAUS: Deluxe TINY*private spa*walk to town
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,236
HK$1,558 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Brooks Motel: Exceptional Suite
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is HK$1,205
HK$2,484 total
includes taxes & fees
3 Jan - 4 Jan 2026
Charming 3-bedroom Cabin for nature lovers
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,574
HK$1,758 total
includes taxes & fees
7 Jan - 8 Jan 2026
Huttopia Berkshires
Property grounds
The Lakeshore House

Holiday Home in Niverville

The Lakeshore House
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is HK$3,769
HK$6,232 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Lakeshore House
Property grounds
3-bedroom house in beautiful Berkshires, close to amenities!

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is HK$1,469
HK$2,474 total
includes taxes & fees
12 Jan - 13 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo in Hancock

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is HK$1,065
HK$2,344 total
includes taxes & fees
6 Jan - 7 Jan 2026
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,462
HK$3,508 total
includes taxes & fees
5 Jan - 6 Jan 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is HK$1,399
HK$3,542 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Holiday Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is HK$1,049
HK$2,890 total
includes taxes & fees
6 Jan - 7 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries
2 bedrooms, iron/ironing board, free WiFi, bed sheets
A stunning, modern Lodge with rustic charm at June Farms!

Cabin in West Sand Lake

A stunning, modern Lodge with rustic charm at June Farms!
10.0 out of 10, Exceptional, (4)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
The price is HK$3,441
HK$6,140 total
includes taxes & fees
4 Jan - 5 Jan 2026
A stunning, modern Lodge with rustic charm at June Farms!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place to stay!! Very clean and very professional team"
Maricel 3-night trip
Posted 16 hours ago
Vacation Village in the Berkshires

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?

Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails: This holiday home rental outside of Canaan is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a library so that you can immerse yourself in your holiday.

How many holiday rentals are there in Canaan?

Choose from 11 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.