Town of Canaan Rentals
From $399 per night (USD)VRBO
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
- Bedrooms:
- 3
- 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 $399 per night (USD)VRBO
From $599 per night (USD)Expedia
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 $599 per night (USD)Expedia
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 $1250 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 $1250 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
From $428 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 $428 per night (USD)VRBO
From $425 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 $425 per night (USD)Expedia
From $688 per night (USD)VRBO
Berkshires Year-Round Home-Great mountain & lake views, sunsets, close to Lenox
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 10
NEWLY RENOVATED This house has some of the most amazing views in the Berkshires, looking west over Queechy Lake; incred ...
From $688 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 $276 per night (USD)VRBO
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 $276 per night (USD)VRBO
From $900 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 $900 per night (USD)VRBO
From $880 per night (USD)VRBO
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 $880 per night (USD)VRBO
From $325 per night (USD)Expedia
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)Expedia
From $316 per night (USD)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 ...
From $316 per night (USD)VRBO
From $442 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 $442 per night (USD)Expedia
From $325 per night (USD)VRBO
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 $325 per night (USD)VRBO
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
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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 ...
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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 ...
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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 ...
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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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From $344 per night (USD)VRBO
Birds’ Nest Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Looking for a cozy summer getaway? Escape to Birds’ Nest Bungalow! This charming vintage 3-bedroom cottage is nestled al ...
From $344 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 $261 per night (USD)VRBO
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 $261 per night (USD)VRBO
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 $382 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 $382 per night (USD)VRBO
From $695 per night (USD)VRBO
Guesthouse & 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 $874 per night (USD)VRBO
Secluded Mtn Escape w\/ Pool, Pond + 360° 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 $874 per night (USD)VRBO
From $395 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 $395 per night (USD)VRBO
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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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From $214 per night (USD)Expedia
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 $214 per night (USD)Expedia
From $290 per night (USD)VRBO
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 $290 per night (USD)VRBO
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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SRC-Hudson Valley\/Berkshires Cultural Corridor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
About this space We welcome you to explore the magic of Sunset Ridge Chalet (aka SRC). Ideally situated within the Hudso ...
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