Town of Canaan, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Canaan, New York on RentalSaver.com!

Town of Canaan Rentals

From $405 per night (USD)
VRBO
Best of the Berkshires & Hudson Valley
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has ...
From $405 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Best of the Berkshires & Hudson Valley
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has ...
From $428 per night (USD)
Expedia
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VRBO
Four season lake side oasis in the berkshirkes
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Four-season lakeside oasis nestled between the Berkshires and the Hudson River Valley and a short walk from family-frien ...
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VRBO
From $293 per night (USD)
Expedia
Newly Renovated Cabin in the Country
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Heartwood Cabin is a freshly renovated rustic retreat nestled in the sleepy hamlet of Red Rock, NY. We just lovingl ...
From $293 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Birds’ Nest Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Looking for a cozy winter getaway? Escape to Birds’ Nest Bungalow! This charming vintage 3-bedroom cottage is nestled al ...
From $315 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Berkshire Rural Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Our Berkshire rural retreat has been in our family for three generations where we’ve regularly rejuvenated with hiking, ...
From $386 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Berkshires Lake House With Private Dock, gunite pool, and Chefs Kitchen
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This newly updated sun drenched Berkshire lake house with newly built private in-ground pool, is the perfect place for a ...
From $700 per night (USD)
VRBO
From $779 per night (USD)
Expedia
Private Tennis court, hot tub & pool Berkshires 13 acre Estate 4 bedrooms
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Welcome to our beautiful and spacious retreat, perfect for a family vacation or weekend getaway with friends. Our home o ...
From $779 per night (USD)
Expedia
From $636 per night (USD)
VRBO
Peaceful Berkshires Year-Round Home - Fabulous mountain and lake views, sunsets
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
NEWLY RENOVATED (Had been unavailable during renovation of lower level) This house has some of the most amazing views i ...
From $636 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Secluded Family-Friendly Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located just 2.5 hours from NYC and Boston, this Cape-style post and beam house is perched on top of a hill with wide op ...
From $400 per night (USD)
VRBO
From $629 per night (USD)
VRBO
Hudson Valley Chalet with hot tub minutes to Chatham
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Now offering sleeping accommodations for 10! Please check out my House guide for many local recommendations! Enjoy ...
From $629 per night (USD)
VRBO
From $969 per night (USD)
VRBO
Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
A getaway with everything you dream of - expansive deck, BBQ, sunset views, private in-ground pool, secluded, wooded, ne ...
From $969 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Welcome to WIndswept Acres in the Berkshire Mts!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
This home is on a 12 acre pastural setting. In the meadow you will see a variety of birdhouses and feeders. Sit back and ...
From $295 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Private home on a Beautiful lake. Large deck for entertaining
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Lakehouse 5 bedroom home. Steps from the lake. Large patio for entertaining . New kitchen, Fully furnished. Washer and D ...
From $390 per night (USD)
VRBO
$Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A\/C, 4 bdrms, 2 bath$
From $255 per night (USD)
VRBO
Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A\/C, 4 bdrms, 2 bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Berkshires-Great Natural Beauty, Culture, Outdoor Activities and Easy Highway Access. Close to Tanglewood. Special Offe ...
From $255 per night (USD)
VRBO
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Expedia
Chic Scandinavian Country Retreat!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful country home in East Chatham. Set in a lush, expansive setting on 4 acres ...
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Expedia
From $240 per night (USD)
VRBO
Hilltop House
Bedrooms:
5
Bathrooms:
4
Sleeps:
9
About this space Hilltop House is the perfect get away for your family! Located on 15 acres, it is the best place to enj ...
From $240 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Near Skiing! Hot Tub, Wood Stove, Pool Table, & Theater Room. Pet friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Sprawl out in this charming home that’s both private and close to everything! Discover everything this ALL SEASON Berksh ...
From $275 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Secluded Mountain Top Lake View in Canaan, NY.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Overlooking Queechy lake, this spacious home with a cook's kitchen and wrap-around deck is a great get-away for family a ...
From $277 per night (USD)
VRBO
From $141 per night (USD)
Expedia
Private Cottage, Come Enjoy Nature!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Experience the captivating charm of a 1920 cottage. Come enjoy and indulge in the tranquility of the spacious f ...
From $141 per night (USD)
Expedia
From $325 per night (USD)
VRBO
NEW! Family-Friendly Berkshire Farmhouse - Pond, Firepit & Woodburning Stove!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Can ...
From $325 per night (USD)
VRBO
From $267 per night (USD)
VRBO
One-of-a-Kind Breathtaking Berkshire Retreat
Bedrooms:
4
Bathrooms:
3
Sleeps:
5
15 Acre One-of-a-Kind Luxury retreat with Close Access to Berkshires/Jiminy Peak with breathtaking views of the Catskill ...
From $267 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
22 ACRE 7 BR PRIVATE ESTATE WITH POOL, GUEST HOUSE AND SWEEPING BERKSHIRES VIEW
Bedrooms:
6
Bathrooms:
7
Sleeps:
15
Your home away from home is the ideal summer retreat, whether you're looking for a private getaway, a place to entertain ...
From $1000 per night (USD)
VRBO
$Berkshires Getaway w\/ Deck & Mountain Views!$
From $280 per night (USD)
Expedia
Berkshires Getaway w\/ Deck & Mountain Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this tranquil 2-bedroom, 1-bath Richmond apartment situated in the foothills of the Berkshires. Complete with ...
From $280 per night (USD)
Expedia
$Hudson River Valley\/Berkshires Rural Retreat$
From $200 per night (USD)
VRBO
Hudson River Valley\/Berkshires Rural Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Nice Cape Cod-style home located in the foothills of The Berkshires and just 11 miles northwest of Lenox and Tanglewood. ...
From $200 per night (USD)
VRBO
From $798 per night (USD)
VRBO
Red Rock Summit - Scenic and Secluded
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Welcome to Red Rock Summit, where well-designed living takes advantage of majestic mountain views at every turn ...
From $798 per night (USD)
VRBO
From $268 per night (USD)
VRBO
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Extraordinary private scenic haven. DOG FRIENDLY! Large fenced-in dog pen. As you enter the long, private, tree-lined d ...
From $268 per night (USD)
VRBO
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Expedia
Home in the woods with Views, Quiet, Gardens, near Tanglewood,
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Be secluded but within a short drive of the many cultural and natural attractions of this beautiful area. This lovely 3 ...
Click For Pricing
Expedia
From $150 per night (USD)
VRBO
Foggy Bottom Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Foggy Bottom Studio was created for budget conscious travelers seeking a getaway without having to rent an entire vacati ...
From $150 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Round House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perched on a hilltop in a Berkshire forest, this bohemian guesthouse is a unique hideaway in a silent, idyllic setting d ...
From $166 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fog Hill Cabin is a peaceful retreat set among the wooded landscape of the Beebe Hill State Forest. The main level featu ...
From $325 per night (USD)
VRBO
Click For Pricing
Expedia
Comfortable and charming 3 Bedroom Retreat-Enjoy Hudson Valley & Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our cottage in the woods! We hope to cultivate a relaxing space for a getaway with friends or family. Our ho ...
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Expedia
$Haddock + Cotter - Chic Farmhouse and Barn w\/ Pool$
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VRBO
Haddock + Cotter - Chic Farmhouse and Barn w\/ Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Haddock + Cotter is a beautifully restored chic + charming country home located in Old Chatham, NY. Built in 1834, the h ...
Click For Pricing
VRBO
From $695 per night (USD)
VRBO
A Guest House & Permaculture Sanctuary in the Berkshires
Bedrooms:
9
Bathrooms:
7
Sleeps:
14
We are nestled in a picturesque valley between the Berkshires and the Hudson River Valley, providing a serene backdrop f ...
From $695 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Historic home in country hamlet. 30 min to Tanglewood, Hudson, Berkshires + more
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lovingly renovated charming house located in the peaceful historic hamlet of New Concord, NY. 2.5 hrs from NYC, 2 hrs fr ...
From $290 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Recently renovated home nestled between Hudson Valley and The Berkshires!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
The Hillside House is a recently renovated (2022), midcentury modern retreat nestled between the Hudson Valley and The B ...
From $400 per night (USD)
VRBO

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Town of Canaan Rentals

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Results: 36 Rentals