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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, (2014)
"All around loved everything about the place! "
The price is AU$120
includes taxes & fees
24 Sept - 25 Sept
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (979)
"Absolutely beautiful "
The price is AU$252
includes taxes & fees
19 Oct - 20 Oct
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is AU$166
includes taxes & fees
23 Sept - 24 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (130)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (120)
"Great stay!"
The price is AU$221
includes taxes & fees
23 Sept - 24 Sept
Micosta Leisure Inn

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$281
includes taxes & fees
23 Sept - 24 Sept
Taborton Harvest Boulder Pines Cabin in the woods

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$727
includes taxes & fees
23 Sept - 24 Sept
Comfortable Berkshires retreat on mtn resort, SISO

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

The price is AU$1,028
includes taxes & fees
29 Sept - 30 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is AU$1,607
includes taxes & fees
23 Sept - 24 Sept
Hancock Village Inn at Jiminy Peak

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

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

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

9.6 out of 10, Exceptional, (91)
"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

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is AU$1,229
includes taxes & fees
23 Sept - 24 Sept
The Lakeshore House

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$281
includes taxes & fees
23 Sept - 24 Sept
Taborton Harvest Timber Trails Unique cabin experience

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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

10.0 out of 10, Exceptional, (167)
"Great property. Lots of space and activities for a large group. All amenities are well maintained and the owner was very responsive and helpful. Had a fantastic long weekend! "
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (64)
"Great value, so much better than all the touristy motels in the area!"
The price is AU$319
includes taxes & fees
23 Sept - 24 Sept
Cozy Rustic Apt in 18th c Berkshire Farmhouse

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is AU$504
includes taxes & fees
29 Sept - 30 Sept
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

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

9.8 out of 10, Exceptional, (147)
"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
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

Find out more about Canaan

Find out more about Canaan

Everything you need to know about Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Canaan holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Canaan holiday rentals we have selected for you start as low as AU$120 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Canaan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This holiday home rental outside of Canaan is located on a lake, and has a fireplace, a balcony 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Canaan?

Choose from 15 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.