Holiday Rentals in Canaan

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Holiday Rentals in Canaan

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is €139
includes taxes & fees
11 Jul - 12 Jul
Deluxe Queen Room with 2 Queen Beds

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

9.2 out of 10, Wonderful, (17)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Beautiful retreat in a lake community to the enjoy the summer season.

10.0 out of 10, Exceptional, (39)
"Great house in the woods. We were there for a spotting event so didn't spend a lot of time at the house. There were great walks around there"
Beautiful retreat in a lake community to the enjoy the summer season.

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (73)
"Great location near town and on a pretty lake. Owners easy to deal with and very responsive. Our family had a great trip to the Berkshires!"
Stay Lakeside This Summer!

4 Mi to Great Barrington: Berkshires Retreat!

10.0 out of 10, Exceptional, (1)
"Cozy little place with great space for dogs. The owner was responsive and ensured we had a lovely stay. "
4 Mi to Great Barrington: Berkshires Retreat!

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

9.4 out of 10, Exceptional, (61)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Large Barn styled vacation home that fits groups with space to spare.

10.0 out of 10, Exceptional, (61)
"Another excellent experience stay at this house!"
Large Barn styled vacation home that fits groups with space to spare.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (215)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (12)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (24)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."
Berkshire Lake at the Pillow, and EV!

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (6)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is €717
includes taxes & fees
23 Jun - 24 Jun
Guesthouse Cabin vacation rentals in Berkshire County

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (72)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is €325
includes taxes & fees
24 Jun - 25 Jun
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.6 out of 10, Exceptional, (24)
"Overall it was a great location for a relaxing girls trip. The hot tub and sunroom were great places to hang out. The pictures were very accurate of the house. We did have some issues with cleanliness and pests that we were not expecting. We would recommend it for a relaxing lakefront thing stay."
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
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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Frequently asked questions

Are there 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.

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

Deluxe Queen Room with 2 Queen Beds: This holiday home rental outside of Canaan is equipped with an outdoor pool, air conditioning and WiFi to help you feel comfortable during your stay.

How many holiday rentals are there in Canaan?

Expedia has 5 holiday rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Eddy Field are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Connecticut Railroad Historical Museum and C H Pease Museum.

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 provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.