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 $511 per night (USD)
VRBO
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 $511 per night (USD)
VRBO
From $486 per night (USD)
Expedia
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 $486 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Four season lake side oasis in the berkshirkes
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Four-season lakeside oasis nestled between the Berkshires and the Hudson River Valley and a short walk from family-frien ...
From $293 per night (USD)
VRBO
From $394 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 $394 per night (USD)
Expedia
From $431 per night (USD)
VRBO
Birds’ Nest Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Looking for a cozy getaway? Escape to Birds’ Nest Bungalow! This charming vintage 3-bedroom cottage is nestled along a c ...
From $431 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
5 acres & a newly renovated 1 bed/1 bath cabin with a huge deck & screened porch overlooking a large pond. All you hear ...
From $304 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Plan your Berkshires by the lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. Perfect for families. Hi-speed S ...
From $289 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Luxury Barn Retreat — All-Season Escape Awaits!
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
An exceptionally private getaway on 8 beautiful acres near Chatham, NY, this historic barn has been meticulously renovat ...
From $412 per night (USD)
Expedia
From $867 per night (USD)
VRBO
10 Acre Country Estate with Pool, Hot Tub & Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Welcome to our serene country estate on a private road with 10 acres! Our home is equipped with a pool, hot tub, mountai ...
From $867 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Yacca House NEW Serene Retreat in Canaan
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to Yacca House, a serene wellness retreat in Canaan, NY. This thoughtfully designed space accommodates up to 8 gu ...
From $454 per night (USD)
Expedia
From $387 per night (USD)
VRBO
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 $387 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Secluded Family-Friendly Home
Bedrooms:
2
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 $493 per night (USD)
VRBO
From $933 per night (USD)
VRBO
Berkshires Lake House With Private Dock, gunite pool, and Chefs Kitchen
Bedrooms:
2
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 $933 per night (USD)
VRBO
From $776 per night (USD)
Expedia
R3Bliss
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Private estate in the Berkshires with 13 acres, 4 bedrooms, private pool + salt water hot tub (all year) indoor + outdoo ...
From $776 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Hudson Valley Chalet
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Now offering sleeping accommodations for 10! Please check out my House guide for many local recommendations! Enjoy ...
From $619 per night (USD)
VRBO
From $924 per night (USD)
VRBO
Dream getaway - mtn views, ski, pool, BBQ, Firepit, Kid friendly, Lakes, WFH
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
A getaway with everything you dream of - expansive deck, BBQ, firepit, sunset views, private in-ground pool, secluded, w ...
From $924 per night (USD)
VRBO
From $449 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 $449 per night (USD)
VRBO
From $569 per night (USD)
Expedia
4-bedroom Queechy Lake House with Private Dock and Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Newly renovated, this lakefront home on Queechy Lake in Upstate New York is fully equipped for lakeside fun! We are also ...
From $569 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to the serene, secluded beauty of Hudson in the Berks, tucked away on a hill in East Chatham. This private retrea ...
From $589 per night (USD)
VRBO
From $616 per night (USD)
Expedia
Private Homestead - Cozy Comforts & Scenic Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Recently re-opened for short term stays! Just minutes from Chatham, NY, and nestled in the heart of the Hudson Valley, t ...
From $616 per night (USD)
Expedia
From $891 per night (USD)
VRBO
La Petite Porte Jaune
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to our stunning Upstate New York retreat, where relaxation meets adventure! This spacious house is the perfect g ...
From $891 per night (USD)
VRBO
From $294 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 $294 per night (USD)
VRBO
From $377 per night (USD)
VRBO
SRC-Hudson Valley/Berkshires Cultural Corridor
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
We welcome you to explore the magic of Sunset Ridge Chalet (aka SRC). Ideally situated within the Hudson Valley/Berkshi ...
From $377 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Spacious 1-bedroom apartment in peaceful East Chatham with WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your peaceful apartment in East Chatham with one comfortable bedroom featuring a queen bed. Enjoy the convenience of 1 1 ...
From $178 per night (USD)
VRBO
From $510 per night (USD)
VRBO
Secluded Mountain and 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 $510 per night (USD)
VRBO
Click For Pricing
Expedia
Hilltop House
Bedrooms:
4
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 ...
Click For Pricing
Expedia
From $330 per night (USD)
VRBO
Enchanting 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 $330 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Cozy cabin in tranquil Canaan NY with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover this superb cabin in Canaan. This 1-bedroom retreat offers WiFi, AC, and heating for an enjoyable stay. Nestled ...
From $235 per night (USD)
Expedia
From $366 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 $366 per night (USD)
VRBO
From $565 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 $565 per night (USD)
VRBO
From $413 per night (USD)
VRBO
6 Mi to Tanglewood: Peaceful Berkshire Apt!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hike On-Site | Surrounded By Nature | Near Wineries & Historical Sites Make the most of your adventure in the Berkshire ...
From $413 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Writer’s Haven!!! 360-degree scenic PRIVACY. YET… just 1/2 mile off the Mass Pike and 15 minutes from Tanglewood, Len ...
From $288 per night (USD)
VRBO
From $184 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 $184 per night (USD)
VRBO
From $982 per night (USD)
VRBO
Red Rock Summit: Mtn Escape w/ Pool, Pond + Views
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 $982 per night (USD)
VRBO
Click For Pricing
VRBO
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
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 ...
Click For Pricing
Expedia
From $274 per night (USD)
VRBO
Berkshire Hideaway w/ Fire Pit & Playground!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Near Wineries & Historical Sites | Screened Porch | Peaceful Location Fine wines, scenic landscapes, and quality family ...
From $274 per night (USD)
VRBO
From $897 per night (USD)
VRBO
Haddock and Cotter a Charming Countryside Stay with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautifully restored 1834 farmhouse blends historic charm with chic, modern comfort. Perfect for hosting family and ...
From $897 per night (USD)
VRBO
From $1637 per night (USD)
VRBO
Guesthouse & Permaculture Sanctuary in the Berkshires
Bedrooms:
8
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 $1637 per night (USD)
VRBO

Search Your Destination Now!

Town of Canaan Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 39 Rentals