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Popular penthouses
Bethel Woods Retreat
4 miles from Monticello, NY100 guests
Bethel Woods Retreat. Cozy, Pet Friendly Cabin w/KING BED, Barn, & Arcade
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.
Together, the house and barn
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From
$750
/hr
4 hr min
Round House Farms
Serving the Monticello, NY area60 guests
Round House Farms. A one of a kind private compound in the Hudson Valley featuring two distinctive homes, an architectural dome home originally designed by French architects, and a spacious four story house, set on 31 acres of private woodland 90 minutes from NYC.
The Dome Home is the centerpiece.
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$1,425 total
before taxes
4 hr min
Malkita Homes
Serving the Monticello, 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
The Darkroom Event Space
Serving the Monticello, NY area5.0 (5)
48 guests
The Darkroom Event Space. 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,
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$1,500 total
before taxes
6 hr min
Villa Sposa
Serving the Monticello, 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
Garrison House
Serving the Monticello, NY area30 guests
Garrison House. This is a 3000 sq ft, 3 bedroom 3 bath, single level modern home. Designed by the world renowned American architect Tom Kundig of the firm Olson Kundig. Completed in 2025.
Concrete floors, board formed concrete fireplace, hand troweled clay plaster walls, white oak ceilings,
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$4,000 total
before taxes
8 hr min
Highland Lake Estate
7.8 miles from Monticello, NY250 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
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From
$399
/hr
2 hr min
Enchanting River - Water Front A-Frame Cabin
Serving the Monticello, NY area5.0 (1)
30 guests
Enchanting River is a magical 2BR 1Bath A Frame home secluded on 4 acres of serine forest nestled beside beaver brook running right below the house. This dreamy get away is just 2 hours from NYC & 2.5 hours from Philly.
This property brings the combination
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From
$125
/hr
4 hr min
Sparrow Cottage
Serving the Monticello, NY area30 guests
Sparrow Cottage. Peaceful house in the Southern Catskills, 2 hours from NYC/NJ and surrounding area. Backyard is perfect for baby showers, birthdays and other small celebrations. The deck can be used as a BBQ area and table set up as well. Cottage is surrounded by trees making it
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$339 total
before taxes
3 hr min
Dreamy Upstate A-Frame
Serving the Monticello, NY area5.0 (1)
20 guests
This dreamy upstate brand new a frame is perfect for photo shoots, small company offsites and retreats and to come work from home. With a gorgeous open living and kitchen space it is the perfect blank canvas for your event / meeting. Plenty of seating options
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From
$100
/hr
8 hr min
Private, luxury chalet with a breathtaking view
Serving the Monticello, NY area15 guests
Welcome to your all season escape, to this funky yet luxury, spacious yet cozy, modern yet classic chalet. Where you can experience the perfect vacation, whether it is outdoors with family and friends or appreciating the art pieces throughout the interior. Greet the evenings
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From
$250
/hr
4 hr min
Vibey Stone House With Huge Yard for Filming or Events
Serving the Monticello, NY area32 guests
This modern stone house has high ceilings with excellent light from it's unique, triangle windows. It totals 4500 square feet with the walkout basement. There is also an old abandoned horse stable on the property, which totals 5 acres. We have a stone
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From
$100
/hr
5 hr min
Midcentury home in Hudson Valley
Serving the Monticello, 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.
...
$1,500 total
before taxes
3 hr min
Industrial Downtown Flex Space
Serving the Monticello, NY area50 guests
We have had plenty of different events held here such as (but not limited to), baby showers, birthday parties, networking events, board meetings, book signings , etc. The space is set up with a large kitchen area including a mini fridge for storing food or beverages,
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$339 total
before taxes
2 hr min
Hudson Valley Wine Cellar
Serving the Monticello, NY area30 guests
The entire area is designed for a great time either with a group of up to 30 or just a couple. There is a 1500 bottle wine cellar with tasting table that seats 10, bar and lounge area with pool, darts, TV 3 different, smaller
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$1,200 total
before taxes
3 hr min
Harana Market
Serving the Monticello, NY area75 guests
Harana Market. Welcome to our picturesque event venue perched right along the banks of Rondout Creek! Combining upstate charm, modern convenience, and scenic waterfront views, this versatile indoor/outdoor space is the ideal backdrop for a wide variety of gatherings.
Centrally located in the Hudson Valley—surrounded by trees and
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$876 total
before taxes
4 hr min
Rosebud Luxury Mountain House
Serving the Monticello, NY area15 guests
Zen on the Ridge: A Japandi Mountain Retreat
Perched overlooking the iconic Gunks, this 4 bedroom, 4.5 bathroom architectural masterpiece seamlessly fuses Japanese minimalism with Scandinavian warmth. Designed to honor its rugged surroundings, the home offers an unparalleled blend of organic luxury and meditative tranquility.
Key Features
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$597 total
before taxes
1 hr min
Modern Scandinavian Mountain House Surrounded by Trees
Serving the Monticello, NY area5.0 (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
Historic Victorian Farm House
Serving the Monticello, NY area60 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
...
$3,000 total
before taxes
4 hr min
Beautifully Designed Chalet Getaway: 5 Min from Main St.
Serving the Monticello, NY area5.0 (4)
15 guests
Nestled for privacy, this beautifully designed getaway offers the perfect blend of comfort and privacy. With convenient access to main attractions, our chalet is an ideal escape. We're 3 min away from the Brooklyn Cider House and a quick drive to local farms, hiking trails, vineyards
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$964 total
before taxes
4 hr min
Alpine Four Season Lodge
Serving the Monticello, NY area50 guests
Alpine Four Season Lodge. Host unforgettable experiences at this year round mountain retreat in Highmount! From the expansive deck with sweeping GreenHill and mountain views to the cozy GrillHaus, this property is perfect for micro weddings (up to 50 guests), intimate dinners, creative workshops, or photoshoots.
Make it a complete event
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$997 total
before taxes
4 hr min
Hip Arty Upstate Farmhouse
Serving the Monticello, 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
Withers Mansion Art House
Serving the Monticello, NY area30 guests
Withers Mansion Art House. 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
Hudson Valley Escape With Stunning View and Hot Tub
Serving the Monticello, 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
Modern Design Loft in Beacon + Hudson River Valley
Serving the Monticello, 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
Uptown Event & Meeting Space with Gorgeous Ceilings & Windows
Serving the Monticello, 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
Uptown Kingston Fair Street Mansion
Serving the Monticello, 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
...
$876 total
before taxes
4 hr min
Most Stylish Country Retreat- curated for shoots, chic, double height ceiling, 3 br 3 bath
Serving the Monticello, NY area20 guests
Approximately 2 hrs. from the city awaits the most beautiful retreat designed by a well known architect. This is a brand new home, no attention to detail has been spared. The house is situated on 5 Acres of private land and encompasses 3200 sf of interior
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$1,393 total
before taxes
7 hr min
Expansive and flexible renovated space with gorgeous floors, 14 ft. ceilings, natural light
Serving the Monticello, NY area5.0 (3)
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 Monticello, 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
Safe Suburban Home w/ Large Outdoor Area for Events
Serving the Monticello, NY area20 guests
Book our home conveniently located in Hamden. We’d love to host you for your next creative project. Please inquire via Peerspace messaging if you have any questions or are interested.
Features:
• 2300 sq. ft
• WiFi
• Existing Furniture
• Lounge Space
• Kitchen
• Natural Light
• Restrooms
• Parking
•Large Outdoor Area
Available
...
From
$125
/hr
3 hr min
Beautiful Mid-Century Oasis in Hudson Valley
Serving the Monticello, 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
...
$2,125 total
before taxes
4 hr min
Silas House Barn
Serving the Monticello, NY area85 guests
Welcome to Silas House Barn, a historic dairy barn dating back to 1840. The barn is situated on 2.5 acres and tucked in the valley of the Catskill mountains. There are two levels to the venue, the lower barn and the upper barn, both
...
$3,600 total
before taxes
12 hr min
A-Frame Mid-Century Home
Serving the Monticello, NY area20 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
Roomy, Multi-purpose Space
Serving the Monticello, NY area40 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
Private Cabin Retreat l Hot Tub + Mountain View’s
Serving the Monticello, NY area10 guests
As you drive up to the property, you’ll pull up to rolling hills framed by majestic mountains, greeted by the crisp mountain air and the allure of our charming cabin. Enjoy roaming our 8 private acres, picturesque sunrise/sunset views, and mesmerizing star gazing as day turns
...
From
$300
/hr
4 hr min
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Updated August 30, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.