Holiday Rentals in North Canaan

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Holiday Rentals in North Canaan

Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
9.8 out of 10, Exceptional, (8)
"We LOVED our stay at this property! It was IMMACULATE!! It’s spacious, comfortable and homey. Our hostess, Andrea, was extremely responsive to any questions we had. We loved walking “down the road” from the property to visit the farms and the winery! Perfect for a family with adult members ( the kitchen set up is AMAZING!! A cook’s delight!) and children as well! The kids have their own playground! Andrea deserves a 10- she’s put a LOT of love and attention into her house."
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is €420
includes taxes & fees
18 Sept - 19 Sept
Cheerful 3-bedroom cottage with woodstove
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (36)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (18)
"Updated and well located"
Stockbridge Home, Come Experience The Berkshires!
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"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
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is €307
includes taxes & fees
24 Sept - 25 Sept
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Private Island - Largest Fresh Water Reservoir in Mass....
8.8 out of 10, Excellent, (6)
"Thank you so much for sharing your Otis home with us. From the moment we walked through the door, we could feel the warmth and energy of great memories shared in this home. Growing up visiting Otis as a kid, it was incredibly special to celebrate my Grandmother's 85th birthday and send off my brother, who is starting his PhD program at Harvard University in Boston. My grandmother and the rest of our family will forever cherish this trip, full of laughter, swimming, and using our boat, which we...
Private Island - Largest Fresh Water Reservoir in Mass....
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (140)
"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
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (18)
"This cabin was perfect for a place to rest and refresh after hiking some of Litchfield area's trails. It was as described by the host and he was very easy to reach with questions. We recommend this cabin as well-located for all that Litchfield county has to offer. "
Newly renovated cottage on the lake!
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (24)
"Everything was clean, and was a very comfortable home for friends and family."
The Goshen Glass Chalet
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (23)
"the Meadows House was very comfortable. Now that there are more grandchildren than children we have outgrown our families lake house. The local hotels are never comfortable for our tall family. The Meadows house was perfect. Beautiful views I wish we had been able to enjoy the hot tub but it was a beautiful week and the lake was calling. we would stay at the Meadow House again. The host was very attentive and checked in (via text)during our stay which was nice."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.2 out of 10, Wonderful, (10)
"We had a lovely long weekend in the Berkshires. The location is beautiful, and we really enjoyed the deck, hot tub, and kayaks. We could have used more towels but otherwise the house was pretty well equipped. Bedrooms were cozy, which didn’t really matter because we were outside most of the time, but could be tough in worse weather. "
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (8)
"This is my second summer renting this house. It's great. Beautiful home, lots of light, in the woods, very comfortable. Our first year we had a rainy Sunday and it was fun to just hang out in. Very clean. The rental contact person was very responsive to a question we had. Five minutes from Jacob's Pillow. Lenox/Lee/Stockbridge are all just a quick drive away. Very quiet rural setting. A deer visited us this year, early on Sunday morning. Love this place."
Berkshires Cabin 2 Mi to Appalachian Trail!
Romantic and Secluded Berkshire's Gem
9.8 out of 10, Exceptional, (11)
"We enjoyed our 2 week stay at this cute rustic cabin. The owner and caretakers were super responsive to our needs during our stay. The only thing that was missing was onsite laundry, but the laundromat was nearby so not a huge inconvenience. Overall, great place to relax in the woods."
Romantic and Secluded Berkshire's Gem
Tranquil 3-BR Waterfront Retreat
9.8 out of 10, Exceptional, (8)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
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Other types of properties in North Canaan you may be interested in

Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (347)
"Very quiet, restful, excellent breakfast"
The price is €109
includes taxes & fees
18 Sept - 19 Sept
Locust Tree Bed and Breakfast LLC
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (64)
"The property is excellent. It is near a cow farm and the smell of the cows' manure is overpowering at times . Not in the Inn, but outdoors."
The price is €151
includes taxes & fees
8 Oct - 9 Oct
Blackberry River Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (988)
"Nice stay, experience a old time inn, but with modern amenities "
The price is €256
includes taxes & fees
25 Sept - 26 Sept
The Red Lion 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.

Frequently asked questions

Can I find holiday rentals in North Canaan?

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

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

Peace and quiet on the lake: This holiday home rental outside of North Canaan is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in North Canaan?

Choose from 7 Expedia holiday rentals in North Canaan for a memorable holiday.

What can I see and do in North Canaan?

Housatonic River and Campbell Falls State Park are a couple of lovely local spots to get outside and enjoy nature. Land of Nod Vineyard and Winery and Great Falls are a couple of places you'll find in the wider area.

What are holiday rentals like in North Canaan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in North Canaan. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.