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From $333 per night (USD)
VRBO
Hip on Warren
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful one bedroom apartment in prime Hudson location. Steps to all Hudson has to offer. Clean and modern. Prime ...
From $333 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Modern Home in Historic Hudson 3 Bedrooms 3 ensuite Baths
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegant, centrally located home in historicdowntown Hudson:Three-bedroom townhouse with three en suite baths (3 walk-in ...
From $588 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to Serenity in the Heart of the Berkshires: A Modern Retreat Surrounded by Nature Immerse yourself in the awe-in ...
From $367 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Waterfalls and Trails at 'The Mills At Green Hole'
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Travel back in time to a secluded and beautiful place known as 'The Mills at Green Hole,' a historic 6-bedroom, 3-bathro ...
From $788 per night (USD)
Expedia
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VRBO
Semi-Secluded House in the woods.
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Lovely 3 bedroom house on 4 acres. This 20 year house is comfortable and warm, 3 miles from Germantown center. Great ...
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VRBO
From $139 per night (USD)
Expedia
Modern Copake Falls Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located on a former 13 acre former horse farm, this full size apartment with private entrance features all new everythi ...
From $139 per night (USD)
Expedia
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VRBO
Broad Reach Farm
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Plan a fabulous family getaway on a working horse farm, all the charm of the 19th century with all the amenities of the ...
Click For Pricing
VRBO
From $180 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 $180 per night (USD)
Expedia
$Newly Renovated \Yellow Door Ranch\ on 7 acres sleeps 10$
From $439 per night (USD)
VRBO
Newly Renovated \"Yellow Door Ranch\" on 7 acres sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This newly renovated "Yellow Door Ranch" is a ranch style one story house with 4 bedrooms and 3 1/2 baths. The locatio ...
From $439 per night (USD)
VRBO
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Expedia
Remodeled historic home w/backyard, steps to farmer's market, coffee, food, bars
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Come stay at our beautiful, historic, late 19th century home situated in the center of the small town of Kinderhook, New ...
Click For Pricing
Expedia
From $493 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 $493 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Cottage at Copake Lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming , newly renovated cottage wIth AC and dock on Copake Lake. Bring your boat to your private dock and boat launc ...
From $291 per night (USD)
Expedia
From $428 per night (USD)
VRBO
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Bedrooms:
0
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 $428 per night (USD)
VRBO
From $1070 per night (USD)
VRBO
Modern Barn House - Hike & Ski Berkshire, Hudson Valley
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This custom-built modern Barn House sits upon 10 acres with views of the hillsides of the Taconic mountain range and the ...
From $1070 per night (USD)
VRBO
From $128 per night (USD)
VRBO
All comforts of home
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Each unit is self-contained with a deck and cozy. Visitors have enjoyed the fact that the property is in a rural, forest ...
From $128 per night (USD)
VRBO
From $136 per night (USD)
Expedia
All the comforts of home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Each unit is self-contained with a deck and cozy. Visitors have enjoyed the fact that the property is in a rural, forest ...
From $136 per night (USD)
Expedia
From $118 per night (USD)
VRBO
All the comfort of home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Each unit is self-contained with a deck and cozy. Visitors have enjoyed the fact that the property is in a rural, forest ...
From $118 per night (USD)
VRBO
Click For Pricing
Expedia
Charming landmark home on beautiful Copake Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Rental, available Monday Aug 23 for 1-2 weeks. Charming, bright, 3 br, 2 bath (plus landing with 2 additional beds). E ...
Click For Pricing
Expedia
From $1170 per night (USD)
VRBO
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
The Swiss Chalet styled house is tastefully decorated with a contemporary but cozy flair with over 5000 Sq Ft of Living ...
From $1170 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 Pricing
Expedia
From $593 per night (USD)
VRBO
Newly renovated house in historic Downtown Hudson
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to "Happiest in Hudson"! Less than a minute walk off Hudson's bustling downtown Warren Street, this brand new ren ...
From $593 per night (USD)
VRBO
From $522 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 $522 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Cottage in the Clouds With Mountain Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Recently renovated 1960's Popular Mechanics kit-home cottage on 63 private acres near the Berkshire's. Enjoy spectacula ...
From $369 per night (USD)
VRBO
From $905 per night (USD)
Expedia
Enchanting cottage in a private oasis
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Newly renovated cottage located at Ingadi Farmhouse, a family owned and run farm situated on 127 acres of land in the Hu ...
From $905 per night (USD)
Expedia
From $805 per night (USD)
VRBO
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, in-ground pool, ...
From $805 per night (USD)
VRBO
From $248 per night (USD)
Expedia
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 $248 per night (USD)
Expedia
From $5040 per night (USD)
VRBO
Taghkanic Glass House
Bedrooms:
7
Bathrooms:
7
Sleeps:
20
Stay in the Taghkanic House, an architectural masterpiece designed by renowned architect Thomas Phifer. This unique mo ...
From $5040 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Cozy Retreat on Copake Lake in our Charming Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into a haven of modern elegance with this newly renovated cottage, a sanctuary of tasteful decor and comfort, avail ...
From $260 per night (USD)
Expedia
From $724 per night (USD)
VRBO
Lakefront Retreat on Robinson Pond - Stunning Sunrise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Three Trees on Robinson Pond is a three bedroom, one and a half bath home with waterfront access and incredible views of ...
From $724 per night (USD)
VRBO
From $249 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 $249 per night (USD)
Expedia
From $376 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 $376 per night (USD)
VRBO
From $249 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 $249 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
Click For Pricing
Expedia
Country home in a park-like setting, perfect for private enjoyment.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
An historic farmhouse on 3 acres of meadow gardens and woods, with views of the open farm fields and the Berkshire mount ...
Click For Pricing
Expedia
From $317 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 $317 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Ideal location for summer and winter activities with plenty of outdoor space.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Tory Hill cabin is located at seven minutes from the Taconic State Park in Copake Falls and four minutes from Catamount ...
From $203 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Charming Columbia County Farm House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A former 1890s inn, this newly renovated farm house sits on 13 partially wooded acres. Located on a quiet country road, ...
From $237 per night (USD)
VRBO
Click For Pricing
Expedia
Hudson Valley Yearly Rental- Hudson New York
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
I named my home Pallet House because when I purchased the property in 2018 it was full of old wood pallets. I love red ...
Click For Pricing
Expedia
From $392 per night (USD)
VRBO
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to max ...
From $392 per night (USD)
VRBO
From $380 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 $380 per night (USD)
Expedia
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VRBO
Award-winning architectural gem, 17 acres, swimming pond, sited in state forest
Bedrooms:
5
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 Pricing
VRBO
From $281 per night (USD)
Expedia
Loblolly Cottage - Enchanting Retreat set among towering pines.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Loblolly Cottage is a peaceful retreat set among towering pines on our property in Germantown NY. This guest suite harke ...
From $281 per night (USD)
Expedia
From $1224 per night (USD)
VRBO
Historic Hudson Valley Barn Complex with Relaxing Grounds
Bedrooms:
3
Bathrooms:
7
Sleeps:
10
Welcome to this retreat in Southern Columbia County. Enjoy the rustic elegance of this 1820's converted barn fully resto ...
From $1224 per night (USD)
VRBO
From $132 per night (USD)
VRBO
Cemetery Schoolhouse #1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We LOVE long term stays!!!! We also really WANT to accommodate the weary traveler who needs accommodations for one nigh ...
From $132 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Restored historic farmhouse on 25 private acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A sunny and spacious farmhouse located in Canaan, NY - at the foot of the Berkshires and the Hudson Valley. This 1870 Sh ...
From $447 per night (USD)
VRBO
From $897 per night (USD)
Expedia
Grand Estate w/ Mountain Views 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 $897 per night (USD)
Expedia
From $408 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 $408 per night (USD)
VRBO
Click For Pricing
Expedia
Hudson Valley: Spacious and Kid Friendly Retreat Near Everything!
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Come enjoy this 2 bedroom, 2 bath home surrounded by forest and acres of protected land. Sleeps up to 6 people and is lo ...
Click For Pricing
Expedia
From $448 per night (USD)
VRBO
Hudson NY Country Cottage, Fireplace, Pond, Hot Tub, NYC 2hrs
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
CASA SOL is the perfect, very private, year-round get-away, nestled on 2 acres in the woods of the beautiful Upstate New ...
From $448 per night (USD)
VRBO
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $524 per night (USD)
VRBO
Near Tanglewood: Historic Summer Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly-renovated Berkshire Hills home where rustic charm meets modern elegance. Ideal for families or groups. The open-st ...
From $524 per night (USD)
VRBO
From $1564 per night (USD)
Expedia
Luxury New 6-Bedroom Modern Farmhouse with Hot tub, nr Golf, Ski, Copake Lake
Bedrooms:
6
Bathrooms:
6
Sleeps:
10
Nestled nr the pristine Copake Lake, a brand-new luxury 6-bed, 5.5-bath modern farmhouse with covered porch, grill, gour ...
From $1564 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Hudson NY’S Country Serenity Guest Suite.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Forget your worries in this spacious, serene space, newly renovated open living and dining area that offers a relaxing a ...
From $247 per night (USD)
VRBO
From $1435 per night (USD)
VRBO
July 4th Weekend~ third night's on us! Boutique hotel vibes. Fab for groups!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
'The coolest breath of fresh air the Upstate hospitality scene has been waiting for!' ~cool.stuff nyc Welcome to LongSt ...
From $1435 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Downtown Hudson Apartment: Walk to Cafes & River!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Embark on a relaxing getaway in upstate New York at this 2-bed, 1-bath vacation rental in Hudson! This walkable haven is ...
From $326 per night (USD)
VRBO
From $781 per night (USD)
VRBO
Saltbox-style residence in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $781 per night (USD)
VRBO
From $2409 per night (USD)
VRBO
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond
Bedrooms:
5
Bathrooms:
9
Sleeps:
20
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $2409 per night (USD)
VRBO
Click For Pricing
Expedia
Home in Germantown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3 bedroom, 2.5 bath has everything you need for the perfect retreat. Sunny rooms, cozy wood burning fireplace, and ...
Click For Pricing
Expedia
From $285 per night (USD)
VRBO
75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Watch the sunrise from the master bedroom, and watch the sunset from the deck! This sweet 1600 square foot ranch house ...
From $285 per night (USD)
VRBO
Click For Pricing
Expedia
Farmhouse with undisturbed, magical views and european decoration
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Germantown Gem with Unparalleled Views Exceptional farmhouse nestled in the heart of Germantown. This unique, classic fa ...
Click For Pricing
Expedia
From $239 per night (USD)
VRBO
Pet friendly, cozy home walking distance to everything Hudson has to offer.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay at our charming home right where it's all happening. Hudson's buzzing restaurants, bars, breweries and shopping are ...
From $239 per night (USD)
VRBO
From $232 per night (USD)
VRBO
magical cabin in the woods
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our ‘Cabin in the Woods’ can be described in many different ways, but simply put it’s nothing short of MAGICAL. Tucked a ...
From $232 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Hudson Restored Farmhouse with Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: Escape to a beautifully restored 1850 farmhouse nestled on 12 acres of rolling hills in Hudson, NY. Enjoy Panor ...
From $425 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Charming 2-bedroom house with WiFi, AC in marvelous Hudson
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom house in Hudson. Located at a five minute walk from the main street of Hudson in a ...
From $312 per night (USD)
VRBO
From $290 per night (USD)
VRBO
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 $290 per night (USD)
VRBO
From $279 per night (USD)
Expedia
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 $279 per night (USD)
Expedia
From $1254 per night (USD)
VRBO
Newly renovated private 3 bedroom house on a dead end road.13 acres & 360 views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your dream upstate country escape! This newly remodeled 3-bedroom, 3-bathroom home offers a perfect blend of ...
From $1254 per night (USD)
VRBO
From $773 per night (USD)
Expedia
Peaceful & quiet 4-bedroom w pool, lovely garden, deck, outdoor shower, WiFi, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Make yourself at home in this sweet 4-bedroom Ghent retreat. This tremendous house boasts 2 king beds and 2 queen beds, ...
From $773 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Sugar Shack - 300 square feet of pure sweetness.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A very Romantic-Private-Peaceful OASIS yet steps from quintessential Main Street lined with restaurants, brewery, shops, ...
From $274 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Private Unit in shared 1830 Farmhouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Johnson Farmhouse, a delightful retreat steeped in charm and history, located in the heart of the picture ...
From $204 per night (USD)
Expedia
From $880 per night (USD)
VRBO
Lakeside Modern Escape Gym • Kayaks • Fireplace
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Wander Hillsdale Lakeside, a stunning lakefront home featuring modern architecture and captivating sunset vie ...
From $880 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Private Hot Tub: Hudson Valley Cabin Retreat!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dog Friendly w/ Fee | Private Pond | Wood-Burning Stoves | On-Site Trail Access Make the most of your next family getaw ...
From $687 per night (USD)
Expedia
From $1053 per night (USD)
VRBO
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
Bedrooms:
7
Bathrooms:
7
Sleeps:
15
Discover this delightful 7-bedroom gem in New Lebanon. This fabulous house boasts 1 king bed, 3 queen beds, 2 twin beds, ...
From $1053 per night (USD)
VRBO
From $953 per night (USD)
Expedia
Restored Landmark Barn in Hudson, 1780 Ice House
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Landmarked fully renovated barn house built from hand-hewn wood in 1780 is a special Hudson experience. On 38 acres of u ...
From $953 per night (USD)
Expedia
From $369 per night (USD)
VRBO
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 $369 per night (USD)
VRBO
From $737 per night (USD)
Expedia
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 $737 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Home w/ Fire Pit, Near Downtown Hudson + Skiing!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Private Sauna | Deck w/ Mountain Views | 13 Mi to Catamount Mountain Your next fun-filled getaway in the Hudson Valley ...
From $341 per night (USD)
VRBO
From $702 per night (USD)
Expedia
A charming private 3-bedroom country house with scenic views and sprawling lawn
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience Old Chatham like a local in this 3-bedroom country house/chateau. This stunning property features 3 bedrooms ...
From $702 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Renovated Country Retreat, 11+ Acres by Evergreen Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover serenity nestled on 11 private acres, just 10 minutes from the charming village of Old Chatham. With 3 spacious ...
From $481 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Sweet 2-bedroom apartment on horse farm in Hillsdale with WiFi and AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Nestled on our horse farm in Hillsdale, this delightful farm-stay has 2 cozy queen bedrooms and 2 full bathrooms with sh ...
From $275 per night (USD)
Expedia
From $1014 per night (USD)
VRBO
Hudson Valley Lakefront Gem: 6 Bedrooms & Private Waterfront
Bedrooms:
3
Bathrooms:
6
Sleeps:
17
Just 2 hours from NYC or Boston, escape to a special retreat in the Hudson Valley! Swim, kayak, or paddle board on sceni ...
From $1014 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Airy Upstate Getaway with a View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect getaway in New Lebanon! This open and spacious home offers stunning views of the New Lebanon Val ...
From $306 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Falls Reach In The Heart of Copake
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Experience the Taconic and Berkshire Mountains from Historic Falls Reach, presented by StayBettr Vacation Rentals. In th ...
From $368 per night (USD)
VRBO
From $151 per night (USD)
VRBO
Beautiful 2-bedroom apartment in New Lebanon
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this apartment in picturesque New Lebanon. This cozy retreat features 2 bedrooms with a queen and full bed, a ...
From $151 per night (USD)
VRBO
From $416 per night (USD)
VRBO
A BEAUTIFUL 3 BEDROOM/2.5 BATH HILLTOP HOME IDEAL FOR GREAT ESCAPES,
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This primary residence property offers an unparalleled opportunity to check in to a heavenly getaway. The 2700 SF home o ...
From $416 per night (USD)
VRBO
From $2394 per night (USD)
Expedia
Private Pond, Movie Room, Gym & Fire Pit | Luxe Secluded Berkshires Estate
Bedrooms:
4
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 $2394 per night (USD)
Expedia
Click For Pricing
VRBO
Near Catamount Resort & Tanglewood: Mtn-View Haven
Bedrooms:
3
Bathrooms:
7
Sleeps:
8
Dog Friendly w/ Fee | 40 Private Acres | Fire Pit | Foosball Table | Swimming Pond Nestled in the charming town of Aust ...
Click For Pricing
VRBO
From $432 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 $432 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
Post & Beam • Stunningly Designed Luxury Home w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the immaculate and professionally-designed post & beam rental home of two New York creatives, including the F ...
From $1036 per night (USD)
VRBO
From $121 per night (USD)
VRBO
Charming Cabin in the Woods. POOL!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Consider this cozy cabin your home away from home while you visit the Hudson Valley and the Berkshires. Tucked in the wo ...
From $121 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Modern Loft with Wood Stove, River Views, Walkable
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step into this modern, loft-style retreat in the heart of Hudson, NY—just a short walk to Warren Street and the Amtrak s ...
From $454 per night (USD)
VRBO
From $1566 per night (USD)
VRBO
Family Estate & Haven in the Hudson Valley - 10 Bedrooms, Riverfront Views, 70ac
Bedrooms:
10
Bathrooms:
10
Sleeps:
20
Step into Midwood Estate, a soulful, art-filled property nestled on 75 private acres overlooking the Hudson River. Origi ...
From $1566 per night (USD)
VRBO
Click For Pricing
VRBO
Modern Country Retreat with Designer Touches Near Lenox, Stockbridge, & Chatham
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the perfect blend of modern design and rustic elegance in this meticulously crafted post-and-beam home. Locat ...
Click For Pricing
VRBO
From $363 per night (USD)
Expedia
NEW RENO Historic Creamery in Berkshires w/hot tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This new place on a historic farm is centrally located in the Berkshires, Hudson Valley, and Capital Region. Within 30 m ...
From $363 per night (USD)
Expedia
From $615 per night (USD)
VRBO
Stylish farmhouse w/fireplace by downtown & nature
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
About this space Relax and unwind in this stylish Hudson farmhouse just 15 minutes from downtown/Amtrak and 2 hours from ...
From $615 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Pondfront Gem Minutes from Hudson’s Best Shops & Cafes | The Stillwater House
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
A soulful sanctuary on the water's edge, where calm mornings, creative afternoons, and cozy nights all have their place. ...
From $378 per night (USD)
Expedia
From $525 per night (USD)
VRBO
Farmhouse Retreat, Outdoor Dining/Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to The Olde Kinderhook House! A spacious, restored farmhouse on 3 private acres in the heart of the Hudson Vall ...
From $525 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Serene Modern Lakefront Escape: Kayaks, Fishing, Firepit, Private Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Lago, your perfect lakefront escape in the Hudson Valley! Enjoy stunning water views, a private dock, co ...
From $443 per night (USD)
Expedia
$★Private Pool★ Spacious Historic 1850s \Bell House\ @ Hillsdale, NY Town Center$
From $641 per night (USD)
VRBO
★Private Pool★ Spacious Historic 1850s \"Bell House\" @ Hillsdale, NY Town Center
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Escape to the 1850s Bell House, a historic 5BR/4.5BA estate in Hillsdale NY, once home to the prominent Bell family. Set ...
From $641 per night (USD)
VRBO
$Restored Historic 1850s Barn \Carriage House\ Studio @ Hillsdale Town Center$
From $192 per night (USD)
Expedia
Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the 1850s Carriage House - a charming 1-bedroom studio tucked inside a restored barn on a historic Hillsdale, ...
From $192 per night (USD)
Expedia

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