Places to stay near Hudson Chatham Winery

The charming farmhouse stands amid lush greenery, framed by mature trees. A wraparound porch invites relaxation, while well-maintained grass leads to the entrance. Large windows allow natural light to fill the interior, enhancing the welcoming atmosphere of the property.

4.98 out of 5 average rating, 148 reviews

Stylish Hawthorne Valley Farmhouse Retreat

Hawthorne is a renovated 1920s farmhouse set on 11 acres of pastoral fields, forest and pond, featuring stylish, comfortable, art-filled white and green rooms. Take in the view from the sun porch, nap on the big L-shaped sofa, share cocktails in the field overlooking the valley, and cozy up by the fieldstone fireplace at night. A fully equipped house, with Watson Kennedy goods throughout. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, with Malin+Goetz & Molton Brown supplies make this your luxe country getaway. Now with unlimited WiFi. The perfect getaway for one to three couples, Hawthorne offers multiple rooms and lots of space for maximum relaxation and taking in the country. >> Enjoy the view from the sun-drenched front porch. >> Nap on the big L-shaped sofa in the living room. The two extra deep Restoration Hardware couches are 7’ long; they also serve as larger than usual single beds >> Cozy up with a book by the fieldstone fireplace in the fully screened back porch (with glass panels in Fall and Winter). >> Share sunset cocktails in the Adirondack chairs up in the field overlooking the valley. >> Cook in the well-equipped kitchen. >> Eat your candle-lit dinner in the dining room overlooking the valley. This is a fully equipped country farmhouse, with Watson Kennedy goods throughout the home. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, and Malin+Goetz bath supplies make this your luxe country getaway. You will be the only guests in the house, with no one else on-site. Lots of hiking in the valley and nearby conservancy areas, biking on country roads, cross-country, downhill or snowshoe during the snowy months, or take in all the antique shops and history year-round. This peaceful property is minutes from the Hawthorne Valley Farm store, 20 minutes to the world-class food and vintage mecca of Hudson, and 30 minutes from the culture and history of Tanglewood, Jacobs PIllow and the Berkshires. For recreation there is hiking in the valley and nearby conservancy areas, biking on country roads, or cross-country, downhill or snowshoeing during the snowy months. Hawthorne is a 2-hour drive from NYC or a 2-hour Amtrak ride from Penn Station to Hudson, and then a 20 minute drive by car or taxi. The house is conveniently close to the Taconic Parkway, while set in a peaceful and quiet valley.

LocationFamilyHiking

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

4.95 out of 5 average rating, 201 reviews

Hudson getaway w/ hot tub+ plunge pool on 20 acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

LocationFamilyWalkability

4.97 out of 5 average rating, 112 reviews

Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

FamilyLocationBiking

4.96 out of 5 average rating, 114 reviews

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

FamilyValueGrill

4.99 out of 5 average rating, 352 reviews

A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.

Cabin in Ghent

Cozy chalet w/ fireplace, deck, by Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

FamilyValueHospitality

The exterior of a two-story yellow house is set among trees under a clear blue sky. A full-width porch with simple wooden chairs and a table invites relaxation. Sunlight filters through the foliage, creating a tranquil atmosphere around the property.

4.95 out of 5 average rating, 157 reviews

Blacksmith House - Charming Historic Getaway

Built in 1790 as a blacksmith shop named “The Town Ax," Blacksmith House was rebuilt in the early 1990's and renovated by the present owners in 2017. The roughhewn beams of the original structure are exposed in every room. Approached by a grand stone staircase, set in a lilac-lined hamlet with plantings, surrounded by wildflowers, furnished with antiques and primitive Americana, Blacksmith House radiates tranquility and graciousness with its full-width front porch and classic proportions.

FamilyValueCleanliness

4.98 out of 5 average rating, 385 reviews

A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.

Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

Blush is a romantic boutique tiny-home getaway with private hot tub in Chatham, NY—just 2.5 hours from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen and curated luxe design. Tucked into a peaceful & private oasis, Blush is located within the artful world of Art Park: A collection of imaginative tiny homes in the walkable village of Chatham, and just a short stroll to restaurants, cafés, shops, cocktails, theatre, brewery. @artparkhomes

LocationValueParks

4.99 out of 5 average rating, 171 reviews

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

ValueLocationOutdoor spaces

4.99 out of 5 average rating, 100 reviews

Farm stay in Ghent

The Farmhouse at Ten Barn Farm

Welcome to The Farmhouse at Ten Barn Farm, a restored historic farmhouse set on a peaceful organic farm surrounded by historic barns, open fields, and the gentle flow of Fitting Creek. Wander the property, relax by the water, enjoy the beauty of nature, and unwind in the private saltwater hot tub beneath a star-filled sky. Original wide-plank floors and a gourmet kitchen create the perfect blend of timeless charm and modern comfort, all just minutes from Hudson and Chatham.

ValueLocationAmenities

A spacious living area features exposed wooden beams and a white brick fireplace with a fire burning gently. Comfortable seating is arranged around a wooden coffee table, and large windows allow for natural light and views of the outdoors.

4.92 out of 5 average rating, 130 reviews

Quiet• pvt farmhouse•stunning mntn views nr Hudson

This welcoming and private 4-bedroom, 2.5-bath farmhouse is a sight to behold. Spacious and sun-drenched, with large windows, exposed beams and an open floor plan, this home looks out over a view from Bear Mountain through the Catskills with stunning sunsets. Here is a blissful sanctuary to relax and recharge, atop a hill on 8 private acres, yet in less than 15 minutes you can be shopping or dining in Hudson. Two stories of space and comfort-- you will want to return!

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The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

4.98 out of 5 average rating, 137 reviews

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

FamilyLocationHeating

A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.

4.98 out of 5 average rating, 126 reviews

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

FamilyLocationSleep quality

Popular amenities for vacation rentals near Hudson Chatham Winery

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Condo rentals with wifi

4.93 out of 5 average rating, 103 reviews

A snowy landscape is presented, showcasing ski slopes and a bustling scene below. A quaint building serves as a backdrop, surrounded by skiers and snowboarders. Tables and chairs are visible, along with ski equipment neatly arranged, highlighting the active atmosphere accessible from the condo.

Condo in Hancock

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

LocationValueKitchen

4.9 out of 5 average rating, 372 reviews

Condo in Albany

Elegant, spacious studio apt in historic mansion

LocationValueBathroom

4.89 out of 5 average rating, 61 reviews

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

Condo in Lenox

Spacious 3 bedroom apt in Lenox historic downtown

FamilyLocationParking

4.89 out of 5 average rating, 93 reviews

A modern kitchen is visible, featuring stainless steel appliances and ample storage cabinets. A dining table set for four is in the foreground, complete with glassware and decorative green accents. Natural light fills the space, highlighting the open floor plan that leads into the living area.

Condo in Lenox

Heart of Lenox!! - Renovated downtown apartment

ValueFamilyCondition

4.77 out of 5 average rating, 65 reviews

A modern living area features a large flat-screen television mounted on a dark green wall. Comfortable seating is provided by a yellow armchair and a blue sofa, draped with a cozy throw. Natural light filters through the windows, with greenery placed tastefully in the corners.

Condo in Albany

2BR w/ Parking + deck - Near Downtown & MVP Arena

FamilyLocationWalkability

4.95 out of 5 average rating, 73 reviews

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

LocationValuePool

4.92 out of 5 average rating, 86 reviews

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

Condo in Hancock

Jiminy Peak Country Inn - ski in/out condo MT view

ValueLocationHiking

5.0 out of 5 average rating, 10 reviews

Condo in Downtown Albany

1840s Historic 2BR/2BA, 12' Ceilings, by Capitol

LocationFamilyIndoor spaces

Family-friendly house rentals

A modern white house, originally an ice house, sits in a grassy setting with large windows reflecting the sunset. Adirondack chairs are arranged around a fire pit, promoting outdoor gatherings. A wooden deck extends from one side, enhancing accessibility to the inviting yard.

4.99 out of 5 average rating, 132 reviews

Hudson Ice House, 25 acre retreat w/ pond & views!

FamilyLocationCheck-in

4.97 out of 5 average rating, 110 reviews

Home in Stuyvesant

The Stuyvesant House

FamilyValueGetting around

4.96 out of 5 average rating, 115 reviews

Home in Athens

Lake House close to Skiing & Indoor Hot Tub

LocationFamilyHospitality

4.99 out of 5 average rating, 324 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

ValueFamilySleep quality

An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.

4.95 out of 5 average rating, 292 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

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A charming country home is showcased, featuring a dark exterior and a vibrant blue door. The spacious deck extends outward, surrounded by lush green grass and vibrant purple flowers lining the front. Tall trees add to the natural ambiance of the peaceful setting.

4.97 out of 5 average rating, 104 reviews

30 Van Wyck, a contemporary Hudson getaway.

FamilyLocationQuiet

An outdoor area is illuminated by warm lights, featuring a hot tub nestled beneath a canopy. Comfortable seating is arranged nearby, surrounded by lush greenery. A wooden deck provides a relaxing space, with a partially enclosed yard that enhances privacy.

4.96 out of 5 average rating, 179 reviews

Vibing Hot Tub Cottage | Pet-Friendly | Hudson, NY

FamilyValuePets

The living room showcases a retro-style sofa reupholstered in warm orange wool, complemented by wooden beams and large windows allowing natural light. Various seating options are arranged around a central coffee table, enhancing the room's spacious feel.

4.96 out of 5 average rating, 418 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

ValueLocationAccuracy

Apartment rentals with air conditioning

A light-filled living room offers large windows with detailed trim, illuminating a dark area rug. Two wooden chairs are positioned beside a round coffee table, while a plush sofa adorned with yellow pillows adds a pop of color. A minimalist lamp and decorative items enhance the space.

4.97 out of 5 average rating, 265 reviews

A Lovely Historic Apartment

LocationFamilyComfort

4.96 out of 5 average rating, 210 reviews

A friendly horse leans through an open window, with soft curtains framing its gentle face. The horse's striking black and white markings are visible, while light filters softly into the room, highlighting the welcoming ambiance.

Apartment in Coxsackie

Susie's Climax Creations

LocationFamilyOutdoor spaces

4.96 out of 5 average rating, 105 reviews

A modern kitchen features rich blue cabinetry paired with a white countertop. A double sink and stainless steel appliances create a functional space. A window allows natural light to brighten the area, while a patterned rug adds warmth to the wooden flooring.

Apartment in Valatie

Apartment w/Hudson-Electric Trail Access

LocationFamilyDecor

A bright living area features a comfortable sofa adorned with decorative pillows in relaxing tones. A vibrant yellow armchair adds a pop of color, while natural light fills the space through large windows with soft curtains. A round coffee table sits at the center, accompanied by a sleek TV stand.

4.95 out of 5 average rating, 384 reviews

Stylish Hudson Getaway

FamilyLocationCheckout

4.94 out of 5 average rating, 339 reviews

Chic Hudson Apartment - In the heart of Hudson, NY

LocationFamilyLong stay

The open living area features large windows allowing natural light to fill the space. A sleek black couch and a leather armchair complement a dining table with wooden chairs. A flat-screen television is mounted on the wall, enhancing the room's modern feel.

4.97 out of 5 average rating, 315 reviews

Thomas Jenkins Guesthouse hudson

ValueLocationPets

4.93 out of 5 average rating, 248 reviews

A spacious bedroom features floral wallpaper with green and pink patterns. A wooden bed is draped with a red patterned coverlet and accented by a decorative pillow. Two windows allow for natural light, and a bedside table with a lamp complements a nearby chair.

Apartment in Athens

1 bdrm apt in Athens on the Hudson

FamilyValueCheckout

4.9 out of 5 average rating, 327 reviews

A spacious living area is illuminated by natural light from large windows. A comfortable sofa is positioned beside a wooden coffee table. A raised dining area is visible, furnished with two chairs and a small table. The kitchenette features open shelving and rustic accents.

Apartment in Catskill

Catskill Village House - Mountain View Studio

LocationValueParking

Other great vacation rentals near Hudson Chatham Winery

5.0 out of 5 average rating, 270 reviews

An open living area showcases exposed brick walls and wooden flooring, complemented by large windows allowing natural light. Two turquoise couches are positioned on a light area rug, facing a modern fireplace. A spiral staircase leads to the upper level, enhancing the space's architectural interest.

Loft in Hudson

Spacious Loft on Warren Street

FamilyValueAccess

4.98 out of 5 average rating, 161 reviews

A bright bedroom features a spacious bed with neutral bedding, framed by wooden walls and beams. Natural light fills the room through a large window, showcasing a glimpse of the outdoor area. A small side table and a decorative plant complement the simple, serene design.

Cabin in Chatham

The Upstate Cabin: A secluded getaway in the woods

LocationFamilyBiking

5.0 out of 5 average rating, 138 reviews

A charming red cottage is framed by lush greenery, with vibrant plants surrounding the entrance. A gravel driveway leads up to the home, inviting guests to explore the surrounding natural beauty. The structure features multiple windows, allowing light to brighten the interior.

Barn in Stuyvesant

Pond Side R & R

LocationFamilyHiking

4.94 out of 5 average rating, 236 reviews

A well-lit studio space features a spacious bed dressed in white linens with decorative pillows. Light wooden cabinets and a dining table with four chairs are visible in the background, complemented by a full kitchen equipped with essential appliances.

Guest suite in Hudson

Harmony Valley Home, bright & inviting studio

FamilyValueWalkability

4.98 out of 5 average rating, 303 reviews

A modern A-frame cabin is positioned among vibrant autumn foliage. The exterior features large triangular windows framed by wood, and a spacious deck surrounds the front. A stacked log wall is visible beneath the deck, creating a natural aesthetic against the landscape.

Cabin in Saugerties

Stunning 2-Bedroom A-Frame in the Woods with Sauna

FamilyValueKitchen

4.96 out of 5 average rating, 199 reviews

The rustic cabin is framed by lush greenery, with a welcoming front porch featuring wooden steps leading up to the entrance. Tall trees and landscaped shrubs create a serene setting. A stone chimney adds a touch of charm to the inviting exterior.

Cabin in Canaan

Newly Renovated Cabin in the Country

LocationFamilyPets

Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

ValueFamilyCondition

4.97 out of 5 average rating, 186 reviews