House in Sag Harbor, NY
10 guests · 6 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Offering thoughtful design and impeccable details throughout, this retreat in Sag Harbor promises to be the sanctuary you’ve always dreamed of. From the stylish modern barn house construction to the expansive two-tiered outdoor seating decks, luxury and comfort spills out of every corner of this luxury residence.
The 3800 square-foot home is extremely accommodating, living up to its barn house design by lending purpose in every detail. The home is just steps from the exclusive bay-side community beach and historic Downtown Sag Harbor, a former whaling and shipping port and long-standing destination of the elite. Between the quaint downtown, private beach access, and sheer opulence and practicality of the home itself, 74 Hillside Drive East presents the perfect trifecta. This truly is a destination worthy of the most discerning of travelers.
Natural light and tranquility pours into this 5 bedroom, 7.5 bath home, with floor-to-ceiling windows covering almost every square foot of its living space. Entertaining has never been more simple, or more stylish, than on this first level - a pure definition of open-concept, effortless living. A welcoming living area with brick Rumford fireplace is exceptionally airy with its double-height ceiling, and option to flow seamlessly to the sweeping adjacent pool deck. The Poggenpohl kitchen is unassuming yet stunning in its polished modernity and provides everything even the most refined culinary artists would expect. Visitors will also enjoy the wine cooler, mini bar, and gourmet coffee bar.
Dine indoors or out, warmed by a poolside wood-burning fireplace and built-in heat lamps, and surround yourself with lush lawns, mature trees, and a zero-edge heated pool and spa.
The master suite has direct access to the expansive upper sun deck, is veiled by automated blackout curtains, and at the center of the room a sleek gas fireplace. Guests are guaranteed optimal comfort and privacy; their rooms are positioned within a designated suite, with three of the bedrooms offering en-suite baths.
Tasteful and palatial decor throughout with an unmatched location central to beaches and charming Sag Harbor, this destination residence has potential to be the most memorable vacation experience yet.
House has outside security cameras on all exteriors side including pool area
Note: Pool/Hot tub is open from Memorial Day though Labor Day and closed thereafter for the winter
The 3800 square-foot home is extremely accommodating, living up to its barn house design by lending purpose in every detail. The home is just steps from the exclusive bay-side community beach and historic Downtown Sag Harbor, a former whaling and shipping port and long-standing destination of the elite. Between the quaint downtown, private beach access, and sheer opulence and practicality of the home itself, 74 Hillside Drive East presents the perfect trifecta. This truly is a destination worthy of the most discerning of travelers.
Natural light and tranquility pours into this 5 bedroom, 7.5 bath home, with floor-to-ceiling windows covering almost every square foot of its living space. Entertaining has never been more simple, or more stylish, than on this first level - a pure definition of open-concept, effortless living. A welcoming living area with brick Rumford fireplace is exceptionally airy with its double-height ceiling, and option to flow seamlessly to the sweeping adjacent pool deck. The Poggenpohl kitchen is unassuming yet stunning in its polished modernity and provides everything even the most refined culinary artists would expect. Visitors will also enjoy the wine cooler, mini bar, and gourmet coffee bar.
Dine indoors or out, warmed by a poolside wood-burning fireplace and built-in heat lamps, and surround yourself with lush lawns, mature trees, and a zero-edge heated pool and spa.
The master suite has direct access to the expansive upper sun deck, is veiled by automated blackout curtains, and at the center of the room a sleek gas fireplace. Guests are guaranteed optimal comfort and privacy; their rooms are positioned within a designated suite, with three of the bedrooms offering en-suite baths.
Tasteful and palatial decor throughout with an unmatched location central to beaches and charming Sag Harbor, this destination residence has potential to be the most memorable vacation experience yet.
House has outside security cameras on all exteriors side including pool area
Note: Pool/Hot tub is open from Memorial Day though Labor Day and closed thereafter for the winter
Amenities at Unique Modern Barn House in Sag Harbor
Non-smoking
Pets allowed
Family friendly
Map of Sag Harbor, NY
Ratings and reviews
10 / 10Outstanding·Oct 2025
Loved the stocked kitchen for cooking. Wish they had spices. Everything clean.
10 / 10Outstanding·Sep 2025
The house was perfect for our group. The 6 en-suite bedrooms allowed all 5 couples to have plenty of privacy. The common areas in the house were excellent and allowed us to spend time together. The hot tub was a huge hit with the entire group. The location was very good, especially the 5 min walk to a beautiful private beach. And the proximity to Sag Harbor was amazing. The street is transition, but the house and location made up for it. We had a fantastic time and would recommend this house very strongly.
10 / 10Outstanding·Aug 2025
Incredible property!! A perfect place if you want to stay in Sag Harbor. Everything is modern and updated. The hosts were very responsive. Everyone in our group absolutely loved the house- will definitely be back!
10 / 10Outstanding·Jun 2025
We stayed at the home in late June 2025. The pictures on VRBO are very accurate, although it appears the house now has a longer table, which means more seating (8 chairs3 at island). Pool now has more seating around the pool (4 luxurious chairs.with 2 large high-end umbrellas). We stayed with eight people… Every bedroom has its own dedicated bathroom, which was very helpful. The pool and hot tub are amazing. I believe the pool and hot tub were saltwater so you can stay in the pool all day long and not have chemical slime on your skin. Both are heated and heat up rather quickly. There is a large weber grill also on the back deck, the back and front deck appears to be teak wood(very smooth/soft on the feet) no exposed screws the wood is attached from the underneath so no splinters or cut feet, etc.. The house is very well equipped with all utensils, pots/glasses,coffee maker, grill kit and one set of washer/dryer on bottom level and another set just off master bedroom making it very easy to wash clothes/towels for a large group(ton of towels provided) The private Bay Beach. Is about a football field down the street and it is a very nice clean beach. We had bicycles which was great, you can ride through the neighborhood almost all the way down to Sag Harbor, you only have to go out onto the main road for about 40 yards and then dive back into the neighborhood ..then you wind by the main marina/harbor in town ..about a 10 to 15 minute bike ride. Awesome stay, highly recommended.
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Top rated by guests
10Outstanding
(21 Ratings)
"Loved the stocked kitchen for cooking. Wish they had spices. Everything clean."
kim V.Don't miss out! Price and availability may change
