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The Maple Overlook Photo Gallery

Explore The Maple Overlook — a private 23-acre estate in Westtown, New York, designed for group getaways, intimate weddings, retreats, and weekends near NYC.

Weddings

Weddings at The Maple Overlook

A private estate backdrop for intimate wedding weekends, rehearsal dinners, ceremonies, and styled celebrations.

Outdoor wedding ceremony overlooking the valley at The Maple Overlook
Bride fastening her wedding shoe in the bridal suite at The Maple Overlook
Wedding dress displayed beneath the chandelier in the bridal suite at The Maple Overlook
Wedding cocktail hour on the barrel terrace at The Maple Overlook — guests celebrating before dinner
Bride and groom portrait on the estate lawn at The Maple Overlook with panoramic Hudson Valley views
Bride walking down the aisle at the outdoor lawn ceremony at The Maple Overlook in upstate New York
Long farm table outdoor wedding dinner beside the pool at The Maple Overlook — florals, valley views, and estate backdrop
Bride and groom making their entrance at the barn at The Maple Overlook — black and white reception photograph
Wedding reception guests celebrating poolside at The Maple Overlook — intimate wedding in the Hudson Valley
Violinist performing on the wraparound deck at The Maple Overlook during the wedding reception
Outdoor wedding reception table with string lights, pool and valley views at The Maple Overlook
Wedding ceremony exit recessional at The Maple Overlook — couple celebrated by guests on the estate lawn
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Explore Intimate Weddings
The Estate

Explore the Estate

From the main house and pool terrace to the barn, padel court, gardens, and open valley views, every corner of the estate is designed for gathering.

Aerial view of The Maple Overlook with the main house, pool, barn and surrounding grounds

Main House

Heated outdoor pool and lawn beside the main house at The Maple Overlook

Pool & Lawn

Upstate NY event space game barn

The Barn

Aerial view of padel court at The Maple Overlook with four players and spectators lounging on the deck — private padel court upstate New York

Padel & Grounds

Upstate retreat rental

Hudson Valley Views — 23 Private Acres

Interiors

Inside the Main House

Bright gathering spaces, a chef’s kitchen, en-suite bedrooms, and thoughtful details for relaxed weekends together.

Professional chefs kitchen at The Maple Overlook — large marble island, subway tile, valley views, upstate New York vacation rental

Chef’s Kitchen

Formal dining room at The Maple Overlook — marble farm table, brass chandelier, navy wainscoting, garden views — private estate upstate New York

Dining Room

Grand living room at The Maple Overlook with floor-to-ceiling windows, stone fireplace, and Hudson Valley views — private estate upstate New York

Living Room

Primary bedroom at The Maple Overlook — king bed, crystal chandelier, shiplap ceiling, panoramic Hudson Valley views through floor-to-ceiling windows, private balcony

Primary Suite

Guest bedroom with en-suite at The Maple Overlook — upholstered queen bed, plaid throw, lawn and paddock views, private en-suite bathroom, luxury upstate New York vacation rental

Guest Bedroom

White en-suite bathroom with glass shower and freestanding bathtub

6 En-Suite Bathrooms

Private bar with dark cabinetry, brass lighting and counter seating

Private Bar

Barn apartment open-plan living and dining area at The Maple Overlook — vaulted beamed ceiling, kitchen, sectional sofa, perfect couple suite for intimate weddings upstate New York

Barn Apartment

Barn apartment bedroom at The Maple Overlook — king bed, industrial pendant light, valley views, open to living area, private couple suite for intimate weddings upstate New York

Barn Apartment — Bedroom

Outdoor Amenities

Pool, Sauna & Padel

Outdoor amenities made for full-estate weekends — swim, play, unwind, and gather without leaving the property.

Heated pool overlooking the Hudson Valley at The Maple Overlook

Heated Pool

Two women playing padel tennis at The Maple Overlook private padel court — outdoor padel venue upstate New York Hudson Valley

Padel Court

Cedar barrel sauna interior with glass door overlooking rolling hills at The Maple Overlook — private estate upstate NY

Panoramic Sauna

Private Bookings

Planning a private stay, retreat, or intimate celebration?

The Maple Overlook is available for exclusive weekend buyouts, weddings, corporate retreats, and milestone gatherings. Limited availability — inquire early.

Inquire About Availability