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Popular penthouses
Victorian Studio
Serving the Shelter Island, NY area125 guests
Victorian Studio. Historic Queen Anne Style Victorian with spectacular stained glass windows is located in the beautiful village of Port Jefferson. This home has a vivid history with many transformations over the past century and a half. The large ornate Parlor has inlaid wood floors, murals on the
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$2,200 total
before taxes
4 hr min
Buddha Belly Records Inc.
Serving the Shelter Island, NY area5.0 (2)
16 guests
Buddha Belly Records Inc.. Cozy Music Lounge with Private Entrance. Great for a photo shoot, business meeting, or private event. Past clients include guest speakers, massage therapists, reiki practitioners, yoga teachers, comedians, psychics, and more. Free high speed Wi Fi. Complimentary organic coffee and organic teas. Easy access to restroom.
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$395 total
before taxes
4 hr min
Stunning Sag Harbor Beach Cottage
3.4 miles from Shelter Island, NY25 guests
Incredible natural light in every room from walls of windows, skylights, and 15 foot ceilings.
Bright, airy, open 3 bed, 3.5 bath home. All bedrooms ensuite and privately situated away from the others. Gut renovated in 2021.
Full of fabulous details heated salt
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$9,250 total
before taxes
12 hr min
1890's Victorian with modern furnishings.
3.7 miles from Shelter Island, NY20 guests
Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Village. The house is dramatic, cozy and very well lit with both ambient and spot lighting on dimmers in all the main rooms. Wifi is strong throughout
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$1,250 total
before taxes
4 hr min
5000 sqft Ultramodern Masterpiece House in Nature
4.8 miles from Shelter Island, NY300 guests
ABOUT THE SPACE
Designed by renowned architect Annabelle Selldorf, this venue is a masterpiece in modern architectural design, mixing exhibition design and a nature rooted landscape concept that invites for a truly human interaction with the outdoors.
Each of the 5000 sqft of indoor rooms (except basement) has
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$9,500 total
before taxes
6 hr min
Classic and chic Hamptons Home
8.9 miles from Shelter Island, NY40 guests
A peaceful retreat bordering a reserve, yet just minutes from East Hampton town and The Hamptons’ beautiful beaches.
Country meets contemporary. The home boasts custom high end finishes throughout, with a wonderful open concept.. The hosts have chosen top of the line decor, towels and linens
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$5,250 total
before taxes
5 hr min
Kismet Hamptons
9.2 miles from Shelter Island, NY30 guests
Enter the gates to a 6,700+/ sq. ft. home that has been masterfully restored with European sophistication, modern and elegant touches. This circa 1920s home has been remodeled and reimagined with the highest standards of construction with no expense spared. The first floor
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$6,700 total
before taxes
6 hr min
Spectacular Private Southampton Estate
Serving the Shelter Island, NY area75 guests
This 6,000 s.f. gated grand and spacious residence with both tennis and pickleball has been totally updated and features 5 bedrooms with 5.5 baths and is sited on 1.84 secluded acres, surrounded by reserves on two sides for complete privacy. As you enter the grand double
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$20,500 total
before taxes
5 hr min
Luminous White 3-Story Open Oasis Home in Amangasett
Serving the Shelter Island, NY area60 guests
A true white marvel, this space is a 3,500 sq. ft. modern retreat nestled on 1.75 acres in Amagansett, just a mile from the main beaches. The open plan ground floor is bathed in natural light, featuring double height 20 foot vaulted ceilings with exposed beams.
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$4,490 total
before taxes
6 hr min
19 Century Farm House in Hamptons
Serving the Shelter Island, NY area40 guests
The Farm house was build in 1810 and we preserved the look. There are 7 bedroom 2 full bathrooms and 2 WCs. It sleeps 10 people. The house has no AC but there are many fans if you want one, at night it always cools
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$1,539 total
before taxes
4 hr min
Modern beach house
Serving the Shelter Island, NY area25 guests
Welcome to your 3200 +/ SF breathtaking 4 bedroom, 3.5 bath home, situated on 1.20 acres with every modern amenity, captivating winter water views on an idyllic setting. Details include, all white oak flooring throughout, soaring open ceilings with tons of natural light pouring in
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$2,750 total
before taxes
8 hr min
Montauk Oasis Fort Pond Sunset Views
Serving the Shelter Island, NY area200 guests
Private events up to 200 people. 2.5 acres of grass land and open area. Ideal space for private dinners, private parties, showers, weddings, graduations, family gatherings, kids parties, wellness retreats, pop up events, photo and video shoots, movie screenings, etc. Curated to your liking or with
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$4,000 total
before taxes
4 hr min
The Green Haven
Serving the Shelter Island, NY area180 guests
The Green Haven is a beautiful backyard oasis filled with meticulous landscape design, large retainer walls, 12'x20' pergola, white porcelain diamond shaped tiles, custom boxwood entertainment system, privacy trees, all year round green artificial grass and sports court. There are hotels and popular restaurants with a
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$3,420 total
before taxes
8 hr min
The Hive Creative Studios
Serving the Shelter Island, NY area5.0 (5)
40 guests
Medium sized event space for workshops and classes. Located in Port Jefferson Station, The Hive Creative Studios is a multi use/multi media creative studio renting private rooms to artists of all varieties. We have 14 private rooms available on site and a large common
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$108 total
before taxes
1 hr min
Spacious Backyard Oasis
Serving the Shelter Island, NY area5.0 (1)
125 guests
Spacious backyard great for any event! Graduations, family reunions, birthday celebrations, you name it, this is the place for you. There is a chic cozy corner you will love for private convos with friends and family. When you're ready to join the party, the yard has
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$849 total
before taxes
4 hr min
Gorgeous East Setauket Lakehouse
Serving the Shelter Island, NY area5.0 (1)
15 guests
Gather up to 15 attendees for this spacious, secluded home with plenty of seating and a big kitchen to host dinner. There's a comfy deck right near a wooded area for some fresh air.
Please inquire via Peerspace messaging if you have any questions or are interested.
Features:
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$619 total
before taxes
4 hr min
Similar searches in Shelter Island, NY
Updated June 28, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.