Holiday Rentals in Canaan

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in 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, (206)
"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
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
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
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
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 €462
includes taxes & fees
6 Oct - 7 Oct
Cheerful 3-bedroom cottage with woodstove
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
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
6 Oct - 7 Oct
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
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
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Peace and quiet on the lake
9.6 out of 10, Exceptional, (191)
"Loved it!"
Peace and quiet on the lake
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (132)
"Quiet and secluded, but close to everything you may need and plenty of wildlife to observe."
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
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!
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (12)
"The property was lovely and the property manager was very friendly and accommodating. The space was ample, beds were very comfortable, and the a/c kept us cool in the middle of a heat wave. Only issue was that the house had a very musty smell to it. Also, the coffee pot was filled with old coffee-apparently they forgot to clean it prior to our arrival. Otherwise a great stay!"
Idillic summer getaway in Litchfield Hills, CT.
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (40)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
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!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Tolland Cabin w/ Private Hot Tub & Grill!
9.4 out of 10, Exceptional, (12)
"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. "
Tolland Cabin w/ Private Hot Tub & Grill!
Don't see what you're looking for?
See all available properties in Canaan
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.
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Canaan you may be interested in

The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (993)
"The Red Lion Inn is a gem of the Berkshires. It is a warm, welcoming place."
The price is €341
includes taxes & fees
3 Oct - 4 Oct
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (533)
"Fun place to stay."
The price is €169
includes taxes & fees
9 Oct - 10 Oct
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1003)
"The floors in the bathroom were sticky and the carpet."
The price is €107
includes taxes & fees
20 Oct - 21 Oct
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.

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?

Peace and quiet on the lake: This holiday home rental outside of 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 Canaan?

Expedia has 4 holiday rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Campbell Falls State Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Haystack Mountain State Park and Great Falls.

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.