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Popular castles
Stunning Country Tudor Estate of Bygone Era
Goshen, NY30 guests
Sitting on 30 country acres, lies a historic Tudor home featuring almost 8,000 sq feet over 3 floors. There are 2 additional guests houses on the property: a 1200 sq feet stone cottage and 2,000 renovated guest home. Both homes are available for rent separately…
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From
$500
/hr
10 hr min
Private Country Retreat with Pool, Hot Tub & Entertainment Spaces
Chester, NY30 guests
Escape to this private 9-bedroom, 4.5-bath retreat nestled on 7.5 serene acres in Chester, NY. This spacious home is perfect for team off-sites, wellness retreats, content shoots, and family-friendly gatherings. The main floor features an open-concept chef’s kitchen, dining area, cozy living room, and direct…
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From
$175
/hr
1 hr min
Mountain View Villa
Woodbury, Highland Mills, NY5.0 (1)
20 guests
Located at the base of Schunemunk Mountain State Park. The property features manicured landscapes, panoramic views from the living room, and a charming creek towards the back. A large outdoor area with cozy seating around the fireplace, and a long dining table for big groups.…
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From
$250
/hr
4 hr min
Rustic 1700's Farmhouse with Recording Studio 1hr from NYC
Warwick, NY20 guests
The Property: This is one of the most cinematically compelling properties within an hour of Manhattan. Built in 1766 and expanded with a center-stack Saltbox structure carefully transported piece by piece from Maine, the nearly 5,000 sq ft estate on Bellvale Lakes Road carries 260…
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From
$250
/hr
2 hr min
Modern Rustic-Luxe home with pool, pond, barns and gardens on 6 acres
Warwick, NY100 guests
4 bedroom home with lots of character set on 6 acres of beautiful, manicured restored farm land. 2500 sq foot home has walk out basement, 3 bedrooms, guest mixed use room, and open concept living space with exposed beams and working fireplace. Reclaimed wood and…
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From
$200
/hr
1 hr min
Historic Victorian Farm House
Warwick, NY25 guests
Timeless elegance in the heart of Historic Town, this Greek Revival estate seamlessly blends 19th-century craftsmanship with modern comforts, offering guests an unparalleled experience. Sophisticated spaces for unique private and social events, including micro-weddings, bridal showers, corporate gatherings, intimate get-togethers, and girls’ getaways. Our historic…
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From
$500
/hr
2 hr min
Historic Stone Boathouse on Tuxedo Lake
Tuxedo, Tuxedo Park, NY5.0 (1)
16 guests
This rare two-story stone boathouse sits directly on the water in the private enclave of Tuxedo Park, just 40 miles from NYC. Built in the late 1800's and beautifully restored, it blends Adirondack, Arts & Crafts, and Hudson Valley lakehouse architecture w modern comfort. The…
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From
$200
/hr
4 hr min
Chic lakeside estate
Hewitt, West Milford, NJ300 guests
Private stylish villa with Pool, Sauna, Pergola, Pickleball & more located 1 hour outside of the city on NY/NJ border. Minutes away from Mt. Peter & Mt. Creek! Reserve this private estate, perfect for a larger group, retreats, & milestone celebrations! With over 10,000 sq.…
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From
$500
/hr
3 hr min
Private 4-Acre Estate Film Location — Pool, Grounds & Speakeasy Lounge
Warwick, NY15 guests
A private 4+ acre estate roughly 90 minutes from New York City — multiple cinematic environments in one fully private location, with no shared access and no foot traffic. Your booking includes the grounds, the heated saltwater pool, and the Cellar lounge: exterior and interior…
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From
$150
/hr
2 hr min
A Modern Cabin in Middletown
Wallkill, Middletown, NY15 guests
Cedar wood cabin home approximately 1500 sq ft on a 2 acre wooded parcel with cleared space front and back yard and fenced garden. Outdoor spaces: We have a front porch that overlooks the front lawn. It is equipt with couch seating and a coffee…
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From
$200
/hr
5 hr min
Beautiful A Fram Cabin in NY
Montgomery, NY5.0 (5)
20 guests
Our A Frame cabin is a fully operating 5 star short term rental located in the heart of the Hudson Valley. The cabin is small in size but makes up for it in its unique charm and beauty. It's here where you can use the…
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From
$100
/hr
2 hr min
1850s Riverfront Carpenter Victorian 2 acres
Cornwall-on-hudson, NY75 guests
This house is a one-of-a-kind space for film shoots, photo shoots, corporate retreats, artist retreats, workshops, weddings, receptions, fitness classes and much more.We have 2 acres of rolling hills, river and mountain views from nearly every window and is made private by the surrounding, lush…
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From
$200
/hr
12 hr min
Upstate NY Luxury Estate with Pool, Padel Court & Scenic Views
Minisink, New York, NY20 guests
Welcome to a private, scenic hillside estate set on 23+ acres with sweeping Hudson Valley views, just over an hour from New York City. This luxurious retreat is the ideal backdrop for photo or video productions, creative projects, and intimate offsite meetings seeking a premium,…
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From
$300
/hr
4 hr min
Quiet cottage
Cornwall, Cornwall On Hudson, NY15 guests
Quiet lovely and spacious house situated in the charming village of Cornwall On Hudson offers privacy plus proximity. Privacy because the house is set back from the street on a flat driveway and sits adjacent to woods, meaning you’ll heard birds more than cars. Proximity…
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From
$150
/hr
3 hr min
Historic Airstream in Countryside Setting with Rustic Barn
Wesley Hills, Suffern, NY30 guests
The 1954 fully restored Airstream sits under a purpose-built pavilion. The entire property stretches over two acres and includes a stream. There is a historic stone house from the 1700s, a pool area, and a wood barn adjacent to the Airstream. The property is a…
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From
$400
/hr
4 hr min
Hudson Valley Mansion with Hudson River Views in Historic City of Newburgh.
Newburgh, NY30 guests
A quick and beautiful 60 minute drive up the Hudson River from NYC. Step back into history in this well-preserved architecturally stunning Fredrick Clarke Wither's Victorian Mansion. (Google him if you don't know) Built in 1866 in Newburgh, NY, it features East facing Hudson River…
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From
$250
/hr
6 hr min
1869 Second Empire Victorian on 1 Acre with Carriage House
Cold Spring, NY100 guests
A beautifully distinctive and photogenic mansard style Victorian house in the historic village of Cold Spring. When built in 1869, this 5,000 sq ft house was considered a mansion. Original exterior and interior period details remain intact including original plaster walls and moldings, leaded glass…
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From
$400
/hr
4 hr min
Stunning historic Victorian house in Newburgh, NY
Newburgh, NY5.0 (1)
10 guests
Stunning Queen Anne style Victorian house in beautiful historic area of Newburgh. The house was built in 1870 and recently renovated. Elaborate mahogany details and stain glass windows are lovingly restored. The entire house is decorated with authentic Victorian furniture and original art work. Main…
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From
$200
/hr
1 hr min
Mid-Century Modern Designer Home with Hudson Valley Views
Newburgh, NY4.0 (1)
50 guests
Welcome to Casa Paloma, a stylishly appointed mid-century modern gem located 60 miles from NYC in the Hudson Valley. The layout is amazing - built around a central courtyard with a koi pond - each generously sized room flows into another and all rooms are…
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From
$390
/hr
4 hr min
Mid Century modern country house situated on a brook on over 5 secluded, wooded acres in the Hudson Valley, including 2 acres of curated botanical gardens
Philipstown, Garrison, NY25 guests
Nestled on over 5 secluded, wooded acres in the scenic Hudson Highlands, this stunning 4,000 sq ft mid-century modern home offers tranquility and is just 60 minutes north of Manhattan. Surrounded by picturesque brooks and natural beauty, including 2 acres of curated botanical gardens, the…
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From
$850
/hr
4 hr min
Italianate Victorian Home
Peekskill, NY5.0 (2)
20 guests
One of a kind, Grand Italianate Victorian located in the historic city of Peekskill. With over 3000 sq. ft. of space, this home has much to offer. Make your entrance up the only iron staircase in Peekskill, up to an elegant front porch. Enter through…
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From
$300
/hr
6 hr min
Modern Design Loft in Beacon + Hudson River Valley
Beacon, NY5.0 (2)
20 guests
Located in the heart of town of Beacon this 1860s brick factory space converted to a modern loft is within the walking distance to everything Beacon has to offer: restaurants and shops of Main Street, walking and hiking trails, farms, breweries, famous Fishkill Creek waterfall…
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From
$300
/hr
12 hr min
Ultra Modern Private Oasis with River Views
Newburgh, NY10 guests
Looking for a picturesque event space rental for your next photo or video shoot, or a stylish and functional meeting or workshop space? Our space is a brand new, ultra-modern oasis nestled high into the hillside with stunning views of the Hudson River and Valley.…
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From
$99
/hr
3 hr min
Upstate Mid Century Modern A-frame Mountain Chalet - Spacious, 2 levels, access to yard and balcony
Beacon, NY30 guests
This house in the mountains is a modern A-frame nestled into the mountains of the Hudson Valley in Beacon. Its proximity to New York City (90 minutes drive or 80 minutes by Metro North Train) spacious interior and breathtaking natural surroundings make it an ideal…
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From
$275
/hr
4 hr min
Hudson Valley Escape With Stunning View and Hot Tub
Newburgh, NY5.0 (1)
20 guests
Welcome to our Hudson Valley Escape With a Stunning View and Hot Tub! 1.7-acre hilltop getaway in the Balmville hamlet, sweeping Hudson River views, 1.5 miles to Liberty Street and Newburgh Waterfront dining, bars, shopping, 12 min to Beacon for Metro-North and all the fun…
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From
$350
/hr
4 hr min
Renovated Gothic Farmhouse in New York’s Hudson Valley
Wappinger, Wappingers Falls, NY50 guests
This Hudson Valley home is a stunning example of a historic Gothic Revival farmhouse that has been masterfully renovated with a bold, eclectic, and artistic interior design aesthetic. Built around 1871, the house seamlessly blends original architectural features with vibrant, modern touches. Exterior The house…
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From
$400
/hr
4 hr min
Similar searches in Chester, NY
Updated September 13, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.