Unique Modern Barn House in Sag Harbor

Sag Harbor, New York
$2137 avg/night Minimum Stay 7 Nights
Bed 6

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 7 nights

Min Stay

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

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    1 Total (up To 20 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 3800 Sq Ft (353 Sq M)
  • KITCHEN

    Coffee Grinder Coffee/tea Maker Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • POOL/SPA

    Fence Around The Pool Heated Pool Hot Tub Outdoor Pool Private Pool
  • BATHROOMS

    5.5 Bathrooms Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    Chinese (Mandarin) English
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request)
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • kim V.

    Submitted Oct 1, 2025

    Stayed Sep 13, 2025

    Loved the stocked kitchen for cooking. Wish they had spices. Everything clean.

  • Melissa F.

    Submitted Sep 30, 2025

    Stayed Sep 21, 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.

  • John B.

    Submitted Aug 3, 2025

    Stayed Jun 30, 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!

  • Wendy K.

    Submitted Jun 30, 2025

    Stayed Jun 23, 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.

  • Tom W.

    Submitted Jan 12, 2025

    Stayed Dec 22, 2024

    My family and I rented the house over the holidays and had an amazing stay. The house has great amenities and George was very attentive and helpful. Would definitely recommend and stay again

  • Gary G.

    Submitted Dec 7, 2024

    Stayed Nov 25, 2024

    I was looking for a quiet luxury home between Boston and New York where our children could meet up with their parents and spend Thanksgiving week. Never been to Long Island/Sag Harbor so I was looking forward to seeing the area. This is a beautiful home with everything, literally. Kitchen and supplied cooking tools and appliances were beyond awesome. A Miele in wall coffee maker. Wed are all foodies so did pretty much all of our own cooking. 3 ovens, one of which is a steam oven. Silverware, plates, glasses; plenty of everything and labels everywhere to put everything back where it belonged. Every room with a private bath. Nice quality linens. Quite neighborhood complete with wild turkeys. The pool and spa were closed for the season. Every sliding door to the patio/pool has an alarm that works and can't be disabled. No children in our group so it was occasionally annoying when went off but I get why they are there. Our children had a chance to relax and unwind from stressful jobs. A few even did some remote work. Good Wifi here too. Short walk to the beach. In short, a perfect home for a family retreat with all adults and still plenty of room for children.

  • Ilyse L.

    Submitted Sep 1, 2024

    Stayed Aug 23, 2024

    We had a great week at george and iris’s lovely home in sag. The proximity of the home to sag harbor shopping and restaurant district as well as haven beach (block away) was great! House was clean, organized and uncluttered. There was space for everyone and my family particularly enjoyed the back porch area which was completely shaded with options lighting and fans and plenty of seating. George was very pleasant and quick to respond.

  • Allison F.

    Submitted Aug 23, 2024

    Stayed Jul 26, 2024

    House is beautiful. It perfectly equipped with a well stocked kitchen, comfortable bedrooms and beautiful furnishings. Owner was very easy to communicate with and open to help with anything.

  • Justin B.

    Submitted Aug 22, 2024

    Stayed Aug 8, 2024

    We had a great stay and would definitely come back!

  • Brett M.

    Submitted Jul 30, 2024

    Stayed Jul 8, 2024

    I've stayed in a few houses in the neighborhood and I've returned to this one. It's in a great location, a block-and-half to the private beach and a five minute drive or 35 minute walk to the village. The house is well designed and beautiful. It feels new, clean and spacious, like a five-star hotel. The two-story windows in the back provide tremendous light and great views of the bird-filled trees. All the bedrooms are en suite which makes a real difference. The large covered deck off the back of the house functions like an additional entertaining space which was great when having guests rain or shine. The pool and spa are perfect. Robert, the property manager, responded to all my questions and needs quickly and efficiently. Couple of suggestions - because the house has most everything you need, the owners might want to stock the kitchen with salt, pepper, cooking oils, coffee and tea and possibly a couple of beach chairs. And I'd like to see privacy shades on the primary bathroom windows. That said - I love this house and I'll be back.

  • jess w.

    Submitted Jul 14, 2024

    Stayed Jun 29, 2024

    Living space was large enough for multiple families and each room offered en suite bathroom. Location was perfect as it offered easy beach access and was close to town.

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Total

Includes taxes and fees
$2,137+
View details