Town of Austerlitz Rentals
- From $833 per night (USD)
VRBO
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Chester! Fall head over heels in love with this gorgeous country home in the tranquil town of Austerlitz, NY. ...
From $833 per night (USD)VRBO
- 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 $958 per night (USD)
VRBO
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
This extremely private luxury home with Catamount Ski views and close to The Barn at Liberty Farms is situated on 33-acr ...
From $958 per night (USD)VRBO
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Expedia
Relax in the Country - Peace, quiet and family friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wake up refreshed to the sound of song birds. The Stay at Spencertown Farm is the perfect place to unwind, sleep late, e ...
Click For PricingExpedia
- From $215 per night (USD)
VRBO
Two Rooms with En-Suite in Quiet Woodland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated two bedroom apartment is nes ...
From $215 per night (USD)VRBO
- From $150 per night (USD)
Expedia
Cozy apartment overlooking our small farm. Family Friendly.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay in our relaxing and quiet barn apartment, new construction with beautiful views overlooking our small farm. T ...
From $150 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Berkshire Barn on 23 Wooded Acres 2BR\/1.5 Bath Sleeps 7
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 7
A private driveway off a quiet road leads to a 1700 square foot loft-like Barn on 23 acres. There are two ponds, stream ...
From $180 per night (USD)VRBO
- From $159 per night (USD)
VRBO
Berkshires Hudson Valley View Cottage - Private & Quiet
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Very private home with 80 acres of field and forest, and sunset view across the Hudson River Valley. Within 30 minutes o ...
From $159 per night (USD)VRBO
- From $395 per night (USD)
VRBO
The Upstate Cabin: A secluded getaway in the woods
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the ...
From $395 per night (USD)VRBO
- From $375 per night (USD)
Expedia
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The Pinetop Cabin is a modern, sustainably built, architect-designed cabin that is the perfect retreat from the city. Th ...
From $375 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Charming, Quiet, River Front
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 13
A cozy modern log cabin nestled in the hills of the Berkshires in a large wooded area with landscaped yard and fishpond. ...
From $279 per night (USD)VRBO
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Expedia
Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Large dining room, spacious kitchen with cozy sofa and chairs in from of wood burning stove, 2 bedroom, library/ yoga / ...
Click For PricingExpedia
- From $240 per night (USD)
VRBO
Quiet Guest House In The Green River Valley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated Guest House is nestled on 10 ...
From $240 per night (USD)VRBO
- From $95 per night (USD)
VRBO
Home Sweet Home in a Best Place to Live Locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunlit home near village green in quiet Spencertown hamlet between Chatham (Columbia County NY) and West Stockbridge (Be ...
From $95 per night (USD)VRBO
- From $243 per night (USD)
VRBO
NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Relax in the country at this idyllic Berkshires post and beam close to skiing at Butternut and Catamount. Twenty minutes ...
From $243 per night (USD)VRBO
- From $1325 per night (USD)
VRBO
Beautiful anytime of the Year.. Sunny Pond will not disappoint.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Come stay with us.. relax and enjoy "The Beauty of the Berkshires". This beautiful renovated Georgian Colonial home s ...
From $1325 per night (USD)VRBO
- From $247 per night (USD)
VRBO
Suite 1 - Quiet and private accommodations in a country setting.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet ...
From $247 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Family&Dog Friendly--40 Acres In Berkshires-minutes from Tanglewood & Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy the country in this sun drenched 4 bedroom, 3 full bathroom quiet home on 40 private acres with stunning views and ...
From $270 per night (USD)Expedia
- From $762 per night (USD)
VRBO
Escape the City! Incredible Hillside Country House. Sleeps 11.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming four-season country home on three beautifully landscaped acres, only two hours from NYC. The house is geared to ...
From $762 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Modern Rustic Artist's Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
I spent a lifetime living and working as a professional fashion photographer in Paris, Milan and New York. My visual se ...
From $200 per night (USD)VRBO
- From $200 per night (USD)
VRBO
It's All About the Mountain Views, Modern Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Separate private entrance of main house to a large, En Suite apartment in fully built out bottom floor. One bedroom with ...
From $200 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Suite 5 - Quiet and private accommodations in a country setting.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet ...
From $242 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Suite 2 - Quiet and private accommodations in a country setting.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet ...
From $350 per night (USD)VRBO
- From $244 per night (USD)
Expedia
Suite 4 - Quiet and private accommodations in a country setting.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet ...
From $244 per night (USD)Expedia
- From $243 per night (USD)
VRBO
Suite 3 - Quiet and private accommodations in a country setting.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet ...
From $243 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 $423 per night (USD)
VRBO
Austerlitz , New York, Columbia County
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Rustic country home with all amenities, spectacular mountain views , large pool with deck, wonderful terraces, and is su ...
From $423 per night (USD)VRBO
- From $980 per night (USD)
Expedia
Chef’s Kitchen, Fast Wi-Fi
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
We are on 35 acres, on top of a mountain and the views of the Hudson Valley mountains are spectacular. Enjoy your first ...
From $980 per night (USD)Expedia
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VRBO
Cute little ranch in the country
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
small ranch on 10 acres of old farmland. cozy little place for a smaller family can sleep 4-6. Inbetween the Catskills ...
Click For PricingVRBO
- From $238 per night (USD)
Expedia
Spacious secluded ranch yet close to Great Barrington, Lenox, & Hudson, NY.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This three-bedroom ranch on 6.5 acres provides all the comforts of home in a secluded bucolic setting. Relax in the gra ...
From $238 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
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Expedia
Charming unique cottage Relax & enjoy the stunning mountains with private views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
What do you love about your property? Views and privacy on top of a quiet mountaintop with acres of private hiking / mo ...
Click For PricingExpedia
- Click For Pricing
VRBO
Award-winning architectural gem, 17 acres, swimming pond, sited in state forest
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 4
Open and serene, the house is cantilevered over our pond, with 360 degree views of the Berkshire hills. Two bedrooms an ...
Click For PricingVRBO
- From $943 per night (USD)
Expedia
Panoramic Views, Indoor Pool by Evergreen Home
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
An ideal retreat nestled in the Berkshires with vast, expansive panoramic views. With 4 BR, 4.5 BA, a brand new gorgeous ...
From $943 per night (USD)Expedia
- Click For Pricing
VRBO
Spring in the Berkshires. Forest, Sun, Huge Deck, BBQ, Firepit, Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Looking for a perfect getaway convenient to the Hudson Valley and the Berkshire Region? The Berkshire BorderWoods House ...
Click For PricingVRBO
- From $1067 per night (USD)
VRBO
Gorgeous large renovated historic home on 10 acres with pool
- Bedrooms:
- 0
- Bathrooms:
- 5
- Sleeps:
- 14
Built it 1850, this incredible home is one the loveliest in the area. Recently fully restored and updated, our 5 bedroom ...
From $1067 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
19th Century Farm House on 300 Acre Farm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sitting on a pastoral 300 acres of active farmland, the Old Ox Farmhouse is a quiet retreat nestled in the heart of the ...
From $1000 per night (USD)VRBO
- From $695 per night (USD)
VRBO
Escape the City! Incredible Hillside Country House. Sleeps 11.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Charming four-season country home on three beautifully landscaped acres, only two hours from NYC. The house is geared to ...
From $695 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
- From $1250 per night (USD)
Expedia
Modern home with Catskill views, guesthouse and heated pool near Chatham\/Hudson
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
A magical place for a big group to lounge by the pool, play ping pong, canoe and cook big meals. The house, designed by ...
From $1250 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Beautiful cabin in the woods close to skiing, hiking and shopping
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Honey Jean Acres! Unplug and unwind at our peaceful log cabin with acres of tranquility. We have so much to o ...
From $425 per night (USD)VRBO
- From $690 per night (USD)
Expedia
Hillsdale Mountain View Estate by Evergreen Home
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
A beautiful estate on a hill overlooking the Hawthorne Valley, with mountain views. Nestled between Hudson, NY and Grea ...
From $690 per night (USD)Expedia
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Expedia
Mountain Views at Fern Hill House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: A beautiful estate on a hill overlooking the Hawthorne Valley, with mountain views. Nestled between Hudson, NY ...
Click For PricingExpedia
- From $259 per night (USD)
VRBO
Deluxe cottage retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Mrs. Arp lived her into her 90's and planted glorious gardens. The all-year creek, resident koi, berries and gardens lur ...
From $259 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the best of the Berkshires and Hudson Valley at the Barn at Bald Mountain! Situated along the mountainous borde ...
From $250 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Private Contemporary Country Chalet
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming chalet situated on the top of a wooded mountainside, with a long, private driveway and 11 acres of woods with a ...
From $300 per night (USD)VRBO
- Click For Pricing
VRBO
Tiny House Amid the Grandeur of The Hudson Valley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretc ...
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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 PricingExpedia
- 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 $346 per night (USD)
Expedia
9 acres of elegant gardens, rolling lawns, wooded paths and a private pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Explore 9 private acres of elegant gardens, rolling lawns, meadows, and wooded paths, complete with an (unheated) privat ...
From $346 per night (USD)Expedia
- Click For Pricing
Expedia
Tranquil Readers\/Writers Retreat on a dirt road in Spencertown, NY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The space The living space is open and bright! There is a charming library (with a ladder), an office nook, a large dini ...
Click For PricingExpedia
- 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 $388 per night (USD)
VRBO
Harmony House in Hudson Valley- Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to the Harmony House, located within walking distance of the charming and historic Chatham town square. This coz ...
From $388 per night (USD)VRBO
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Expedia
Four Seasons Luxury at 'Summerhill', Chatham, NY
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Listing description Enjoy our beautiful home perfectly located to experience the beauty of the Berkshires. Spend time on ...
Click For PricingExpedia
- From $353 per night (USD)
VRBO
Renovated Chatham Home ~ Half Mi to Downtown!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Discover a quiet retreat in this stunning 4-bedroom, 2.5-bath vacation rental in Chatham, NY. Unwind and enjoy the charm ...
From $353 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $606 per night (USD)
VRBO
Book This Summer, Private Oasis, Pool + Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Nestled on a sprawling 16.5 private acres of land, this home offers a serene retreat from the outside world. As ...
From $606 per night (USD)VRBO
- From $568 per night (USD)
Expedia
Hudson Valley and The Berkshires getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Welcome to the Hudson Valley getaway. Located in the heart of the Hudson Valley in Hillsdale NY, sits our 4 be ...
From $568 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Beebehill house\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautifully designed modern retreat is the perfect escape in the Hudson Valley. Kick back and relax in this calm, stylis ...
From $500 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Saltbox-style residence in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $267 per night (USD)Expedia
- From $2310 per night (USD)
VRBO
Sunny Pond by AvantStay | Secluded Estate w\/ Private Pond, Gym, & Movie Theater
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Escape to the enchanting retreat of Sunny Pond, a charming estate nestled on a private pond among the serene forest of t ...
From $2310 per night (USD)VRBO