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Popular penthouses
The Darkroom Private Lounge
Serving the Highland, NY area5.0 (5)
48 guests
The Darkroom Private Lounge. Cornwall’s original firehouse built in 1905, is now operating as a private lounge. Original exposed brick, hardwood floors, and high ceilings make the well appointed studio appear very spacious with a classy vibe. The space is perfect for micro weddings, Sweet 16, anniversary, birthday, bachelorette, engagement,
...
$1,500 total
before taxes
6 hr min
Malkita Homes
Serving the Highland, NY area5.0 (1)
100 guests
Malkita Homes. Situated at the base of Schunemunk Mountain State Park, this property offers a distinctive and versatile setting ideal for creative projects, events, and gatherings. The space features beautifully manicured landscapes, panoramic views from the living room, and a charming creek at the back. The expansive outdoor
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$2,300 total
before taxes
4 hr min
Company House
Serving the Highland, NY area100 guests
Company House. A historic 1912 Victorian estate set on 5.5 bucolic acres. The home has 7 bedrooms and 4.5 bathrooms spread out over 4 floors of living space.
The entire home is surround on 3 sides by a sprawling covered porch and a modern deck and 6 burner
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$6,750 total
before taxes
12 hr min
Golden Crown Cabin
Serving the Highland, NY area30 guests
Golden Crown Cabin. This is a 6 bedroom, 8 bed, and 2 bathroom multi family cabin that sits on 5 acres in the heart of East Jewett, NY. It is surrounded by tall trees providing a secluded and private experience. Although it feels secluded it is just 8 minutes
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$1,095 total
before taxes
4 hr min
Bethel Woods Retreat
Serving the Highland, NY area100 guests
Bethel Woods Retreat. Cozy, Pet Friendly Cabin w/KING BED, Barn, Arcade, & Hot Tub
3 bed, 2 bath house with 2 Queen sized pull out couches
3 level barn with arcade, pool and ping pong table, full bath, and loft area with 2 full sized
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From
$750
/hr
4 hr min
Villa Sposa
Serving the Highland, NY area5.0 (1)
50 guests
Villa Sposa. The Space
This extravagant rental home offers luxurious decor and furnishings from across the globe to help you experience an opulent haven like no other. Complete with 2 bedrooms and 2.5 bathrooms, it features luxuries including a master suite fit for royalty with ensuite jacuzzi, gorgeous wooded
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From
$450
/hr
4 hr min
A-Frame Mid-Century Home
6.1 miles from Highland, NY20 guests
Set at the end of a private cul de sac, this mid century (built 1967) A frame is a spacious open concept 3 bedroom, 2 bathroom home. A large great room (living room) with 23 foot high ceilings, dual fireplace, and floor to ceiling windows, flows
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$2,550 total
before taxes
6 hr min
Modern Scandinavian Mountain House Surrounded by Trees
9.2 miles from Highland, NY5.0 (3)
100 guests
Newly built, beautifully designed house with modern Scandinavian aesthetic, high cathedral ceilings, and large windows with seasonal mountain views and year round horse stable views.
Located in the heart of the Hudson Valley just 5 minutes from Mohonk Mountain and close to town of New Paltz,
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$931 total
before taxes
3 hr min
Roomy, Multi-purpose Space
9.7 miles from Highland, NY40 guests
It is a wide open space of over 450 square feet. It has great lighting and a hand painted accent wall with mountains if you need a cool background. There are plenty of outlets in the space. It also has its own entrance/exit separate from the
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$173 total
before taxes
2 hr min
Uptown Kingston Fair Street Mansion
Serving the Highland, NY area30 guests
Located on doctors row in historic Uptown Kingston, this nearly 5000 square foot Italianate mansion is available for a wide variety of uses. Available for photo and video shoots as well as special events. An elegant and grand home with five bedrooms, and four baths. The
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$876 total
before taxes
4 hr min
Uptown Event & Meeting Space with Gorgeous Ceilings & Windows
Serving the Highland, NY area5.0 (1)
50 guests
Event & meeting space in a private clubhouse setting with gorgeous vaulted ceilings, many windows with abundant natural light. 3 Private meeting rooms and open communal area for events, two phone booths for private calls and large bar/kitchen area designed in chic mid century modern motif.
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$1,175 total
before taxes
4 hr min
Architectual Cabin in the Woods w/ Floating Bedroom
Serving the Highland, NY area4.9 (7)
14 guests
Featured on Cabin Porn Aug. 2022
Quintessential cabin in the woods on a private lake (35 acres) in the middle of 12 acres of forest. Architectural light filled cabin featuring privacy, land, and a floating cabin on lake. Cabin is two hours from NYC in Dutchess
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$2,350 total
before taxes
6 hr min
Hudson Valley Escape With Stunning View and Hot Tub
Serving the Highland, NY area5.0 (1)
15 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
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$1,400 total
before taxes
4 hr min
Beautiful Mid-Century Oasis in Hudson Valley
Serving the Highland, NY area5.0 (1)
25 guests
This stunning mid century modern retreat is located on 7 acres of private land, close to NYC and other upstate hamlets. With a hot tub, fireplace, and floor to ceiling windows in each room, it offers 360 views of the surrounding forest. Perfect for nature and
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$2,125 total
before taxes
4 hr min
Contemporary 21st Century Residential Event Space
Serving the Highland, NY area5.0 (1)
65 guests
Colonial, Contemporary, 21st Century home located in a beautiful tree lines golf course neighborhood.
located in the sought out Hopewell Junction neighborhood, The Legends,
and set in and around the Beekman Golf Course, with its very beautiful
tree lined neighborhood. No HOA.
On the first level; Two story foyer, Office
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$1,250 total
before taxes
4 hr min
Beekman Arts Club
Serving the Highland, NY area5.0 (1)
50 guests
Beekman Arts Club. The barn was built around 1835, the same time as the adjoining mansion. The structures is very rustic with hand cut beams as long as 30' sitting across the space. The ceiling is 3 stories high in the main room and there are other wings, nooks
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$1,800 total
before taxes
4 hr min
Historic mansion with 12 acres
Serving the Highland, NY area25 guests
Historic mansion with 12 acres. Beautiful Federal/Greek revival mansion built in 1835 and recently finished major renovation. The house is rebuilt with new central heating /air conditioning, bathrooms, electricity, plumbing, etc. The property is surrounded by 12 acres of land with mature trees and well maintained lawn with several flower gardens.
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$1,095 total
before taxes
4 hr min
Hudson Valley Mansion with Hudson River Views in Historic City of Newburgh.
Serving the Highland, NY area30 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
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$1,041 total
before taxes
4 hr min
Modern Design Loft in Beacon + Hudson River Valley
Serving the Highland, NY area5.0 (2)
8 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 and
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$6,300 total
before taxes
12 hr min
Midcentury home in Hudson Valley
Serving the Highland, NY area50 guests
Hi I've curated an inspirational space for artists, creatives and those who want to enjoy the beauty of Hudson Valley. This space is good for photo shoots, production, gallery, offsites, dinners, events.
This is a passion project that I hope you find aesthetically pleasing.
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$1,500 total
before taxes
3 hr min
Expansive and flexible renovated space with gorgeous floors, 14 ft. ceilings, natural light
Serving the Highland, NY area5.0 (1)
60 guests
The 1,000 sq ft, ground floor, front studio is perfect for any type of celebration birthdays, engagements, baby showers, bar and bar mitzvahs, dance parties, karaoke, rehearsals, and corporate meetings. The ceilings are 14 ft with natural wood beams, floor to ceiling glass windows
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$243 total
before taxes
2 hr min
A Beautifully Renovated, Flexible Space for Celebrations, Photo Shoots, Rehearsals
Serving the Highland, NY area5.0 (2)
50 guests
The 1,000 sg foot, ground floor front studio, with 14 ft ceiling, features beautiful natural light, vinyl hardwood floors and wooden beams. It includes, a kitchenette, tables and chairs as needed, as well as SONOS surround speaker system. The cubby room includes storage, a bathroom,
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$348 total
before taxes
3 hr min
Mid Century Home with Wood Paneling
Serving the Highland, NY area20 guests
Perfect for shooting. Have hosted fashion campaigns and catalogues, as well as editorials. The home has two rooms with wood paneling, and the furniture is photogenic with a mix of new and vintage mid century. The home is on 3 acres which provides many opportunities for
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$755 total
before taxes
4 hr min
Hip Arty Upstate Farmhouse
Serving the Highland, NY area20 guests
This unique artist owned farmhouse faces a picturesque creek. It's a beautifully updated and meticulously maintained arts and crafts farmhous near Woodstock, NY.
The property sits on 1.5 acres, boasting extensive blue stone terraced gardens and lush landscaping that create the perfect setting for outdoor shoots. It's
...
$876 total
before taxes
8 hr min
Amazing Country home in the Hudson Valley on top of a mountain.
Serving the Highland, NY area12 guests
Large ground areas. Ultra large swimming pool with table and umbrella and six chairs plus four chaise loungers. Great hiking areas. Five bedrooms. Three Full size bathrooms. Massive kitchen area with large marble island. Sub Zero Refrigerator. Large Induction stove. Large outdoor patio with table and
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$1,095 total
before taxes
4 hr min
Mountain Lodge
Serving the Highland, NY area98 guests
Situated just outside the charming town of Tannersville, New York, The Lodge is a magnificent mountain retreat. This recently renovated property sprawls 6,500 square feet, boasting 13 bedrooms, 8 full and 1 half bathrooms. Complete with gorgeous wood accents throughout, the warm interiors create a cozy
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$8,498 total
before taxes
3 hr min
Spacious, Sophisticated Lounge Designed for Entertaining
Serving the Highland, NY area4.7 (10)
35 guests
Our club room offers the ideal space for meetings, team events, parties and presentations. Versatile enough to host groups up to 35 people.
INCLUDED IN YOUR BOOKING:
Seating for up to 28
Tables and chairs
Kitchenette equipped with sink, microwave, and mini refrigerator
...
$348 total
before taxes
3 hr min
Main Living Area in a Cool, Quirky Historic House Built in 1719 on 11 Acres
Serving the Highland, NY area40 guests
The space includes the main living area in a beautiful antique country home surrounded by 11 acres. Built in 1719, the space features a gourmet kitchen with sitting area, fireplace, island and 11 foot dining table. The living area wraps around the center fireplace
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$255 total
before taxes
1 hr min
Charming Storefront
Serving the Highland, NY area100 guests
This is a charming Hudson storefront on Warren Street with plenty of natural light and cozy ambiance. It has oak hardwood floors and gallery track lighting with halogen bulbs. It has two large front windows and several windows in the front and back space, so it
...
$263 total
before taxes
1 hr min
Hudson Valley Home for Events
Serving the Highland, NY area24 guests
Fully Renovated Historic Resort Lodge between Hudson River and the Catskills, two hours north of NYC. Formerly Hotchkiss House Resort and Hotel, built in 1900, and situated on 9.6 acres. This is not your grandmother's farmhouse. Renovated newer foundation and steel beams through the length, many
...
$855 total
before taxes
4 hr min
Modern venue rental with one of the best views in the Hudson Valley
Serving the Highland, NY area75 guests
Looking for a great venue for your celebration? Or perhaps book your class, workshop or retreats, etc.
•Private use of Venue
• 2 rooms
• Chic Bathroom
• 1,700sq/ft.
• Parking designated space
• Utilities included
• Use of outside yard
• Wifi included
• Modern Space
• Catering options
...
$740 total
before taxes
4 hr min
Forest Shangrila Estate. 6 Acres of Maintained + Wild Land. Private Lake + Streams + Bridges + Infinity Decks + Wildlife. Located in Westchester, NY - 45min from NYC
Serving the Highland, NY area5.0 (2)
115 guests
Shangrila in Chappaqua, NY. 45 min train from NYC. Property is less than a mile from train station. Beautiful Dodge Farms Colonial set on over 6 acres of lush, green property with rare specimen plantings, extensive stonework, outdoor built in grill with bar seating, covered outdoor
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$4,346 total
before taxes
4 hr min
Exquisite Bedford Luxury Farm house
Serving the Highland, NY area30 guests
Escape to the enchanting town of Bedford, NY, where a world of tranquility and luxury awaits you. Nestled amidst rolling hills and picturesque landscapes, our exquisite space offers the perfect blend of rustic charm and modern comforts.
This impressive 3 bedroom, 2.5 bathroom haven promises an unforgettable
...
$1,095 total
before taxes
2 hr min
Barn 46 Hudson Valley
Serving the Highland, NY area5.0 (1)
20 guests
Barn 46 Hudson Valley. An original 1800s, mortise & tenon construction, barn hayloft with a soaring vaulted roofline and flooded with natural light. The owners have maintained the old soul of the space making it a unique gem in the Hudson Valley.
Space is excellent for photoshoots, providing a rustic vibe.
...
From
$120
/hr
1 hr min
Panoramic Mountain Views with Private Pond on 10 Acres
Serving the Highland, NY area29 guests
The chalet was custom built on the back corner of a 10 acre lot, overlooking a private pond and 10 acres of grass and trees and the Catskill mountains. All of the windows are perfectly oriented so there are breathtaking mountain views from every bedroom, only
...
From
$300
/hr
4 hr min
Highland Lake Estate
Serving the Highland, NY area250 guests
Lake + Garden Cottage (2 homes) on 22 Acres with Hot Tub Save now when you book months in advance, additional savings on stays 3 days and longer Ask about any current special promotions we may be running, and additional accommodation options
...
From
$399
/hr
2 hr min
Similar searches in Highland, NY
Updated June 4, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.