Holiday Rentals in East Canaan

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Holiday Rentals in East Canaan

Peace and quiet on the lake
9.6 out of 10, Exceptional, 187 reviews
"Cute & clean house, awesome location right on the water, great for swimming/fishing/kayaking plus super close to the store for any supplies. Thanks again!"
Peace and quiet on the lake
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, 195 reviews
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is €321
includes taxes & fees
1 Jul - 2 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 5 reviews
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, 2 reviews
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is €456
includes taxes & fees
8 Jul - 9 Jul
The Blue Elm - A Historic Berkshire Cottage
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, 49 reviews
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is €259
includes taxes & fees
8 Jul - 9 Jul
Perfect Vacation Get Away - Historical New Marlborough
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, 8 reviews
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.6 out of 10, Exceptional, 7 reviews
"We were racing at Southwick motocross park. This location appealed to us because it had a lake to swim in, nice quiet neighborhood and house looked cozy. Everything was amazing. The local stores, restaurants and things to do was great. This is a very quiet neighborhood and so relaxing. The house was great, all amenities were as described. We really enjoyed it."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, 39 reviews
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 21 reviews
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, 4 reviews
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
'The Mill River Cabin’ w/ Fireplace & River View!
9.8 out of 10, Exceptional, 33 reviews
"We had a great time during our stay at the Mill Creek cabin! The views of the river couldn't be beat & we enjoyed spending time reading on the porch & watching the wildlife from the huge living room windows. We will definitely be back!"
'The Mill River Cabin’ w/ Fireplace & River View!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, 6 reviews
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, 8 reviews
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, 140 reviews
"Perfect home on Otis Lake with plenty of room for a group of friends to gather. Kitchen was fully stocked with all the utensils, pots/pans, dishes to make a nice meal. Beds were very comfortable. Plenty of outdoor furniture to gather near the fire pit by the lake. Keurig coffee maker available to make coffee in the morning. Nice and quiet, felt very private. Plenty of room for parking. Thanks for letting us rent."
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, 80 reviews
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
Beautiful retreat in a lake community to the enjoy the summer season.
10.0 out of 10, Exceptional, 31 reviews
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat in a lake community to the enjoy the summer season.
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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.

Other types of properties in East Canaan you may be interested in

Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, 330 reviews
"Heidi does a great job overall. Very accommodating on our late check in. Great breakfast. Nice room with private. Outside veranda on 2nd floor is nice to have drinks and snacks. "
The price is €113
includes taxes & fees
1 Jul - 2 Jul
Locust Tree Bed and Breakfast LLC
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, 912 reviews
"Classic hotel but our room was far from main desk and fairly inconvenient. Room was in a separate annex "
The price is €246
includes taxes & fees
1 Jul - 2 Jul
The Red Lion Inn
Quality Inn
2.5 star property
8.2 out of 10, Very good, 930 reviews
"Staff was courteous "
The price is €132
includes taxes & fees
21 Jul - 22 Jul
Quality Inn
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.

Everything you need to know about East 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 East Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 East Canaan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

East Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in East 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A East 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 East Canaan holiday rentals we have selected for you start as low as €259 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on East Canaan rentals

At Expedia, we put the best East 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 East 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 East 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 East 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 East Canaan?

Yes, there are holiday rentals close to the most popular sights in East Canaan, or you can select a more secluded option if you're looking for a relaxing stay. East Canaan is known for its wineries.

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

Beautiful Getaway - Right on the Lake-Close to Skiing: This holiday home rental outside of East Canaan is located on the beach, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in East Canaan?

Expedia has 3 holiday rentals for your stay in East Canaan.

What’s there to see and do in East Canaan?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Great Falls. In the wider area, you’ll find Land of Nod Vineyard and Winery and Infinity Music Hall and Bistro.

What’s a holiday rental in East Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in East Canaan. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.

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