Canaan Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Canaan holiday rentals

Terrace/patio

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is HK$1,763
HK$2,808 total
includes taxes & fees
26 Apr - 27 Apr
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,333 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is HK$675
HK$840 total
includes taxes & fees
23 Apr - 24 Apr
Vacation Village in the Berkshires
Room

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is HK$987
HK$1,443 total
includes taxes & fees
23 Apr - 24 Apr
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,535
HK$4,336 total
includes taxes & fees
21 Apr - 22 Apr
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (142 reviews)
"Steven is the most helpful and kind host I've ever experienced! The property is lovely, and the rooms are cozy. I would definitely recommend staying here especially as a solo traveler."
United States
Salvio
The price is HK$1,018
HK$1,140 total
includes taxes & fees
4 May - 5 May
Micosta Leisure Inn
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,431
HK$3,506 total
includes taxes & fees
16 Apr - 17 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is HK$979
HK$1,434 total
includes taxes & fees
23 Apr - 24 Apr
Taborton Harvest Boulder Pines Cabin in the woods
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$2,812
HK$5,688 total
includes taxes & fees
21 Apr - 22 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,433
HK$10,402 total
includes taxes & fees
23 Apr - 24 Apr
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$768
HK$1,036 total
includes taxes & fees
22 Apr - 23 Apr
All comforts of home
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,857
HK$3,955 total
includes taxes & fees
20 Apr - 21 Apr
Cheerful 3-bedroom cottage with woodstove
Dining

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
The price is HK$1,332
HK$2,396 total
includes taxes & fees
16 Apr - 17 Apr
Pet-Friendly Hudson Escape w/ Hot Tub
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,586
HK$2,480 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Riverside Berkshires Retreat
TV, fireplace

A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (5 reviews)
"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$3,469
HK$6,111 total
includes taxes & fees
19 Apr - 20 Apr
A stunning, modern Lodge with rustic charm at June Farms!
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (29 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,586
HK$2,516 total
includes taxes & fees
20 Apr - 21 Apr
Home in Great Barrington
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,232
HK$4,015 total
includes taxes & fees
17 Apr - 18 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Living area

Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet

Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet
Hudson
The price is HK$1,622
HK$3,667 total
includes taxes & fees
16 Apr - 17 Apr
Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet
Outdoor dining

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

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,108
HK$3,860 total
includes taxes & fees
17 Apr - 18 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,721
HK$6,746 total
includes taxes & fees
22 Apr - 23 Apr
Spacious 5-bedroom house in charming Lee with WiFi
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,175
HK$1,492 total
includes taxes & fees
16 Apr - 17 Apr
The Brooks Motel: Exceptional Suite
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"For an old roadside motel they have turned this into the coziest little place. The library is charming, the rooms are cool and comfortable and the food was wonderful. Highly recommend "
Molly 2-night trip
Posted 11 hours ago
Berkshires Untold

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?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Canaan is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Canaan?

Choose from 8 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.