Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Canaan Vacation Homes

Our top choices for Canaan vacation homes

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

Mid Century Modern Studio w/ Full Kitchen - Newly Built

9.0 out of 10, Wonderful, (2)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
The price is CA $270
CA $345 total
includes taxes & fees
Aug 25 - Aug 26
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

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

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is CA $224
CA $551 total
includes taxes & fees
Sep 3 - Sep 4
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
CT Gate House Goshen CT, Gate House Goshen CT
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (2)
"The property was great and the house was huge even for all 12 of us "
The price is CA $286
CA $1,067 total
includes taxes & fees
Aug 25 - Aug 26
CT Gate House Goshen CT, Gate House Goshen CT
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is CA $257
CA $705 total
includes taxes & fees
Aug 25 - Aug 26
Perfect House In Hillsdale, Brings Friends & Fam
Cozy & fully remodeled 4-bedroom house in fantastic Litchfield with central air
Private kitchen

Cozy & fully remodeled 4-bedroom house in fantastic Litchfield with central air

The price is CA $311
CA $575 total
includes taxes & fees
Aug 25 - Aug 26
Cozy & fully remodeled 4-bedroom house in fantastic Litchfield with central air
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is CA $260
CA $419 total
includes taxes & fees
Sep 1 - Sep 2
Home in Great Barrington
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is CA $221
CA $544 total
includes taxes & fees
Sep 3 - Sep 4
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Charming Retreat at Stone Hill Estate – Nature Meets Luxury
Dining

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (1)
"Great experience overall! Property is beautiful and the guest home is situated nicely with access to the backyard and pond. Everything was very clean and well kept with everything in the home that we needed. The hosts were very kind and welcomed us making the stay enjoyable. Would recommend. "
The price is CA $553
CA $984 total
includes taxes & fees
Aug 26 - Aug 27
Charming Retreat at Stone Hill Estate – Nature Meets Luxury
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is CA $518
CA $715 total
includes taxes & fees
Aug 25 - Aug 26
Bungalow in the Berkshires
Charming 3-bedroom Modern cottage with lakeside views
Property grounds

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
The price is CA $1,244
CA $2,055 total
includes taxes & fees
Aug 27 - Aug 28
Charming 3-bedroom Modern cottage with lakeside views
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is CA $328
CA $695 total
includes taxes & fees
Sep 3 - Sep 4
Cheerful 3-bedroom cottage with woodstove
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is CA $449
CA $788 total
includes taxes & fees
Sep 2 - Sep 3
Great Barrington Get Away
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $588
CA $1,103 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 5-bedroom house in charming Lee with WiFi
rural, serene + sophisticated space
Interior

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is CA $413
CA $607 total
includes taxes & fees
Sep 14 - Sep 15
rural, serene + sophisticated space
Deluxe Queen Room with 2 Queen Beds
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is CA $137
CA $184 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
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

The Little Lion

The Little Lion

10/10 Excellent
"staff was very responsive and we were pleasantly surprised by how fresh smelling the rooms are. Not always so in motel settings.We would definitely stay there again. Bess ruff ruffed her approval as well."
cathy 5-night trip
Posted 20 hours ago
The Little Lion