Columbia Area Rentals
- From $468 per night (USD)
VRBO
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely everyone that has been here loves the setting. Read the >100 5 Star reviews first…. This is a beautiful pa ...
From $468 per night (USD)VRBO
- From $2150 per night (USD)
VRBO
4 Br, Hudson River Manor on 65 acres, with pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Holcroft is a private, 65-acre country estate on the Hudson River in Columbia County that offers old-world charm and ele ...
From $2150 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Silver Ridge: sweeping views in luxury chalet
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Silver Ridge is a perfectly-sited contemporary mountain lodge, perched high on the hills above Hillsdale, with ...
From $370 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of the Berkshires, equidistant from NYC and Boston, this newly equipped and renovated carriage hous ...
From $200 per night (USD)VRBO
- From $385 per night (USD)
VRBO
3 Br Cottage on Historic Hudson Valley Estate - Near Bard College
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This beautiful wood-paneled cottage is nestled in the woods on a private 87-acre former Livingston Family Hudson Valley ...
From $385 per night (USD)VRBO
- From $277 per night (USD)
VRBO
Heavenly Kinderhook Lake!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Lakefront home with dock and brand new added boat and swim lower dock. Deck for relaxing and sunning yourself or to unwi ...
From $277 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Garden Suite with private parking, In The Heart Of Hudson
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
An art filled Garden Suite located in the heart of Hudson - on Warren Street - allows walking to all the restaurants, an ...
From $175 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Ski Central Charming Farmhouse 24 acres 8 min 2 Catamont 25 Hudson\/Gt Bar
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
LOCATION IS PERFECT! * Min to Catamount, 40 Min to Butternut, Jimmy Peak, 5 min to COPAKE Lake, located between Gt Barri ...
From $292 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Large Pool + New spacious 4 BR home - walk to Gym, Tennis & Boating on Lake!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Large 4 BR, 2.5 Bathroom with extra den and huge kitchen! In addition, there is a large outdoor deck with seating for 10 ...
From $465 per night (USD)VRBO
- Click For Pricing
VRBO
A cozy retreat to the farm life.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored ...
Click For PricingVRBO
- From $267 per night (USD)
VRBO
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 $267 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Pool-Pond-Privacy <br>Country Chic Near Hip Urban Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Year round upstate retreat: Privacy and seclusion abound! Located on a quiet country road, this 3 bedroom contemporary h ...
From $360 per night (USD)VRBO
- From $410 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 $410 per night (USD)VRBO
- From $396 per night (USD)
VRBO
Nordic Cabin: cozy winter haven
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: The White Mills Nordic Cabin is a mid-century, Scandinavian-inspired home on 6-acres of woods on a quiet countr ...
From $396 per night (USD)VRBO
- From $456 per night (USD)
VRBO
Modern Glass House designed by renowned architect Thomas Phifer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We invite you to stay with us in our two bedroom all glass-house designed by renowned architect Thomas Phifer. A perfect ...
From $456 per night (USD)VRBO
- From $183 per night (USD)
VRBO
La Petite Maison, Chatham, NY
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet, country setting one mile from downtown Chatham Village with private parking. Enjoy a very comfortable stay with m ...
From $183 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Secluded Country Getaway On 22 Magical Acres. Catamount ski resort 5 min away
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
The adventure awaits in the Berkshires. Escape the hustle and bustle of your everyday life and come chill in a renovated ...
From $400 per night (USD)VRBO
- From $128 per night (USD)
VRBO
Rural charm in Ancram, NY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy peaceful, light-filled pastoral views from this charming 19th century home, completely rebuilt from the ground up ...
From $128 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 $880 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 $880 per night (USD)Expedia
- 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 $750 per night (USD)
VRBO
Sweeping Mountain Views in the Berkshires
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Mountain views in the Berkshires for every season! Country home in quiet neighborhood on 11 acres surrounded by farms. ...
From $750 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Carriage House Charmer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fairland Farm is located on County Route 21, Kinderhook, 20 min. from Hudson, NY and 2.5 hours from New York City. Fair ...
From $180 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Home on Malden Bridge, Columbia County, New York
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay at our beautiful, historic, late 19th century home situated in the center of the small hamlet of Malden Bridg ...
From $275 per night (USD)VRBO
- From $721 per night (USD)
VRBO
Beautiful Waterfront Home in the Foothills of the Berkshires
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Introducing an exquisite 6-bedroom family retreat nestled on 6 acres of pristine landscape with exclusive waterfront acc ...
From $721 per night (USD)VRBO
- Click For Pricing
VRBO
Historic Hudson Valley Home in the Berkshire Foothills
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
In the middle of nowhere and the heart of everything, our Hillsdale retreat offers quaint shops and food within walking ...
Click For PricingVRBO
- From $383 per night (USD)
VRBO
Superb Views -- Sunsets, Mountains, Valley
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summer 2024 overview: June, available 6/1 to 6/21 July, available 7/5 to 7/12 August, fully rented ...
From $383 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 $900 per night (USD)
VRBO
Copake Lake House with Private Lakefront
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy the lake in a luxury waterfront home. Soaring ceilings and views of the lake and mountains will take your breath a ...
From $900 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 $835 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 $835 per night (USD)VRBO
- Click For Pricing
VRBO
Jenny’s Folk Art Museum
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Jenny’s Folk Art Museum is a historical home built in 1770 and located in the picturesque village of Kinderhook. Althoug ...
Click For PricingVRBO
- Click For Pricing
VRBO
Beautiful private cottage rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Very private, 2 story farm house cottage set on 24 acres of rolling green lawns and wooded land. There are direct views ...
Click For PricingVRBO
- From $220 per night (USD)
VRBO
Modern Country Cottage, close to ski\/snowboard. Retreat and Relax.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away on a quiet private road, this 4-season home offers a sunlit living space with double height ceilings. In add ...
From $220 per night (USD)VRBO
- From $182 per night (USD)
VRBO
CREEKSIDE CABIN w\/ EXTRAS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Brand-new, and overlooking a stream that runs to the Hudson river, our Cabin has been kitted out with all modern ameniti ...
From $182 per night (USD)VRBO
- From $682 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 $682 per night (USD)VRBO
- From $999 per night (USD)
VRBO
Federal style house on Armory Square in downtown Hudson
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Recently renovated Federal style house across from the Hudson Public Library. The house was completely renovated with a ...
From $999 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 $375 per night (USD)
Expedia
Quaint, Picturesque Country Farmhouse near Bard College, Omega & HITS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Surrounded by beautiful flower gardens and green grass, the main house boasts three bedrooms and two full baths. The hou ...
From $375 per night (USD)Expedia
- From $306 per night (USD)
VRBO
Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Upscale centrally air-conditioned lakefront cottage with 75 feet of lakefront property and a Landlord who lives to make ...
From $306 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Little Red Hen is an old school house from the 1900 hundred.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
It was completely renovated in 2008. It is 2 hour north of New York City and about one hour south of Albany NY. It is cl ...
From $125 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $259 per night (USD)
VRBO
Berkshires dream house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Charming 4 bedroom house two hours from NYC nestled in the Berkshire mountains. Warm up by the wood burning stove. Liste ...
From $259 per night (USD)VRBO
- From $180 per night (USD)
VRBO
The Artist’s Studio - Cool country chic guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A 1,400 sq. ft. light-filled, architecturally designed split-level guesthouse. Large, open-plan living space with full k ...
From $180 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Beautifully Renovated Exposed Beam Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
If the dates are showing not blocked - these dates are available and we are accepting bookings. One of the few brick G ...
From $185 per night (USD)VRBO
- From $475 per night (USD)
VRBO
All Season Country Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A private country cabin tucked back from the road with open lawn and wooded areas. A large pool (June-August), hiking tr ...
From $475 per night (USD)VRBO
- From $274 per night (USD)
VRBO
Berkshires 4br\/2ba, MEMORIAL TO LABOR DAY, '24
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BERKSHIRES - 4 BR/2BA - Spring &/Or Summer, '24. (Prefer Memorial to Labor Day. PRICE IS BASED ON FULL SEASON RENTAL, BO ...
From $274 per night (USD)VRBO
- Click For Pricing
VRBO
Rip Van Winkle Bohemian - Riverfront Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Writer's escape with panoramic riverfront sunsets. Nested in the banks of the Hudson River, features 3 BR, 2 Full BA, an ...
Click For PricingVRBO
- From $159 per night (USD)
VRBO
Stylish, clean and bright 2 BR apt just off of Warren Street!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Picture a lovely standard queen hotel room. Now add a full kitchen. Now add an extra bedroom that can be used for a sing ...
From $159 per night (USD)VRBO
- From $214 per night (USD)
VRBO
Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sweet retreat perfectly located for exploring Columbia County, the Berkshires, or simply lazing on the lawn with lemonad ...
From $214 per night (USD)VRBO
- From $266 per night (USD)
VRBO
A 200 year old center hall colonial between the Berkshires and the Hudson River
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This property is located on an acre in a small village within easy walking distance of a gourmet country store, a tavern ...
From $266 per night (USD)VRBO
- From $571 per night (USD)
VRBO
Beautiful Upstate New York Farmhouse for up to 7 Guests
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Surrounded by farms and pastures yet only seven miles from Hudson, NY, our well-appointed farmhouse is perfect for famil ...
From $571 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Modern, Minimalist, Light-filled Home with Hot Tub Near Catamount Ski
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our modern, light-filled house is like a cabin in the woods, but bigger, with plenty of space and lofty ceilings. The ho ...
From $358 per night (USD)Expedia
- From $220 per night (USD)
VRBO
Beautiful, Unique Country House w\/Large Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming and cozy 2 story, 1 bedroom country house, perfect for couples looking for the meditative beauty of an artist's ...
From $220 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Swim in private pool on 8 acres, hike & shop Warren St. Minutes from Hudson
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
First Floor Home Details: -Living room with decorative brick fireplace, high ceilings and double doors open to an enclos ...
From $700 per night (USD)VRBO
- Click For Pricing
VRBO
Hudson Home with Scenic Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax, rejuvenate and refresh in my beautiful newly renovated Hudson home. My home has unique Scenic Hudson River and Mo ...
Click For PricingVRBO
- From $540 per night (USD)
VRBO
Lake House- amazing sunsets, kayaks, fire pit, family friendly (sleeps 6).
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your own personal oasis and stunning lake vistas in this very private 3 bedroom, 3 bathroom home. Lake views from ...
From $540 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Beautifully Restored, Secluded Farmhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Tucked away on private lane and bordering hundreds of acres of preserved land, this tastefully renovated 1840 farmhouse ...
From $450 per night (USD)VRBO
- From $356 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 $356 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Hudson Old Chatham Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
If the dates are showing not blocked - this means that the dates are available and we are accepting bookings. When you ...
From $175 per night (USD)VRBO
- Click For Pricing
VRBO
Private Hillsdale Home With Views Of Catamount.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedroom three bathroom home located at the end of a country lane in hillsdale NY. 6.8 miles to catamount ski area ...
Click For PricingVRBO
- From $304 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 $304 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 $325 per night (USD)
VRBO
Waterfront Escape +dock +kayaks +firepit +fireplace +games
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everythi ...
From $325 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Upstate NY Getaway. 2 hrs from NYC. On Copake Lake. Minutes to Catamount Mtn.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located in Columbia County nestled in seven secluded, wooded acres, Green Glass is a contemporary farm house centrally l ...
From $500 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Escape to Hudson NY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our Hudson house is a great weekend (or week-long) escape! Light-filled open Victorian is furnished with an eclectic mix ...
From $250 per night (USD)VRBO
- 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 $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 $520 per night (USD)
Expedia
Large Barn styled vacation home that fits groups with space to spare.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Main space open living-dining-kitchen, covered porch overlooking the lake with sofa area table and chairs gas fire table ...
From $520 per night (USD)Expedia
- Click For Pricing
VRBO
Sun-Drenched Property Steps from Warren
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is ideally located 2 blocks/3 min. walk to Warren Street (the main commercial street in Hudson). We are a 10 mi ...
Click For PricingVRBO
- From $247 per night (USD)
VRBO
Elizaville Twin Lake Retreat
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 9
Located on one of Elizaville's beautiful Twin Lakes, this home is a year-round retreat where you can relax and enjoy bea ...
From $247 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Beautiful 3 BR Berkshire Home - Mountain Views and Privacy on 10 Acres
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, bright & clean 3 bedroom home is not a 'rental' house (we use it as our family ski house all winter). It sits ...
From $400 per night (USD)VRBO
- From $356 per night (USD)
VRBO
2,000 sq ft loft located \"downtown\" with access to dining..shops...movie theater
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on Main Street in “downtown” Chatham, chathamLoft75 is a 2,000 sq ft fully furnished second floor space that has ...
From $356 per night (USD)VRBO
- 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 $800 per night (USD)
VRBO
ONLY 2 AUG WEEKS LEFT. Private 4B\/4bath with POOL, TENNIS, PICKLEBALL, BOCCE..\n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Playground in Paradise. A bucolic retreat, this completely secluded estate, nestled on 65 acres, offering your exclusiv ...
From $800 per night (USD)VRBO
- From $635 per night (USD)
VRBO
Have it all! Lakefront, Pool & Skiing & Gym! 5 Bedrooms
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Located in a peaceful and serene neighborhood, this home has it all! Huge double height Great Room with stunning large ...
From $635 per night (USD)VRBO
- From $573 per night (USD)
VRBO
Designer Home with Panoramic Views near Hudson
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Architect designed published modern home sits atop a secluded private hill. Surrounded by great estates and horse farm. ...
From $573 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Beautifully decorated & immaculate log chalet on 3 acres, winter views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with he ...
From $200 per night (USD)VRBO
- From $1181 per night (USD)
VRBO
Hudson Hilltop Retreat
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to a “Four Season Adventure Seeking” property located on six pristine hilltop acres with rolling meadows, 15 min ...
From $1181 per night (USD)VRBO
- From $175 per night (USD)
VRBO
3 BR Lake House with Gorgeous Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the quiet confines of Sincere D'Amore nestled in the heart of the Taconic Mountain Range in Columbia County, ...
From $175 per night (USD)VRBO
- From $431 per night (USD)
Expedia
Cozy Chic Home near Catamount Skiing w\/ Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom family friendly home that is newly renovated with a beautifully landscaped, garden w/ 2 outdoor couches, hammo ...
From $431 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bright, airy and cozy contemporary lakefront home with 4 Bedrooms (SEE BELOW FOR BED LAYOUT), extra high ceilings in liv ...
From $425 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Casa Bartolo, Your Oasis on the Hudson!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience true country living and wake up to a beautiful scenery of the mountains and river at this whole second level ...
From $300 per night (USD)VRBO
- From $1057 per night (USD)
VRBO
Spectacular Private Hilltop Contemporary Estate (Pool\/Catamount\/Bash Bish Fall)
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This fully renovated contemporary estate has it all to make it your place to escape all year round. Sitting on 11 pri ...
From $1057 per night (USD)VRBO
- From $950 per night (USD)
VRBO
Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This home has breathtaking views stretching all the way to the Catskills. A lovely pool welcomes in the summer and the ...
From $950 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Restored 1810 Farmhouse in Hillsdale, NY
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our sensitively renovated 1810 farmhouse just minutes away from the best the Berkshires and Hudson Valley has to o ...
From $245 per night (USD)VRBO
- From $242 per night (USD)
VRBO
Beautiful Getaway - Right on the Lake-Close to Skiing
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Beautiful 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutte ...
From $242 per night (USD)VRBO
- From $115 per night (USD)
VRBO
Cozy Fox Cottage near downtown Hudson
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
*not available: currently hosting a long term renter* Less than 5 miles from Hudson's bustling Warren Street, tucked aw ...
From $115 per night (USD)VRBO
- From $707 per night (USD)
VRBO
Hudson River\/Catskill Mtn Views 2 Bdrm Contemporary, Hudson NY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy spectacular Hudson River and Catskill Mountain views with as much as 50 miles of visibility from this home. This C ...
From $707 per night (USD)VRBO
- From $950 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 $950 per night (USD)VRBO
- From $2100 per night (USD)
VRBO
The Martin Van Buren historical hunting lodge \/ camp
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Four saison cottage The historical Van Buren property (former hunting lodge and camp) is nestled on 26 acres on a priva ...
From $2100 per night (USD)VRBO
- From $545 per night (USD)
VRBO
National Register Historic Hudson River Estate Carriage House
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
This home was just redone, to maximize your comfort. There are 4 bedrooms: a master bedroom with a king bed and master b ...
From $545 per night (USD)VRBO
- From $592 per night (USD)
VRBO
Peaceful, Sun-Drenched Cottage & Guesthouse on Copake Lake – Dramatic Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Also accepting reservations on our new listing (Lakefront on Robinson Pond): https://www.vrbo.com/2233168 COPAKE LAKEHO ...
From $592 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Bungalow Hudson - cozy 3 BR house with huge garden - steps from Warren Street!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful home in the heart of downtown Hudson with great light and an amazing garden that integrates perfectly with the ...
From $263 per night (USD)VRBO
- From $495 per night (USD)
VRBO
Quiet Country Getaway 4BR\/3BA W\/ Pool Hot Tub \/ Movie Theatre
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located on an idyllic country road, our house offers the perfect retreat for your getaway. Whether you are on vacation, ...
From $495 per night (USD)VRBO
- From $740 per night (USD)
VRBO
Lakefront 4-Season Stunning Home and Guest House W\/Tennis Court & Full Gym
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Gorgeous Lake views! Sun streams through windows all day long in this bright airy contemporary lakefront home and newly ...
From $740 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Farmette Roquette Hudson Valley
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
The Farmette is a working flower farm owned by event producers and caterers. We love rustic modern spaces and enjoy dec ...
From $625 per night (USD)VRBO
- From $173 per night (USD)
VRBO
Martin Van Buren lake cottage 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Four saison cottage NYC comfort on a wooded private lake retreat If you are a nature lover and like comfort then this ...
From $173 per night (USD)VRBO
- From $173 per night (USD)
VRBO
Hudson: Martin Van Buren lake cottage IIII (4)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Four season cottage If you are a nature lover and like comfort then this place is for you. Former home of the Martin Va ...
From $173 per night (USD)VRBO