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Holiday Homes in Shelter Island

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Featured Holiday Homes in Shelter Island

The Hampton Sack a cheerful relaxing beach cottage
7.6 out of 10, Good, 13 reviews
"The place was exactly as expected and advertised. A nice place to relax at the end of the day with everything you need to rest and recover. Absolutely lovely location and just an overall great place to get away for a weekend"
The Hampton Sack a cheerful relaxing beach cottage
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, 18 reviews
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
9.0 out of 10, Wonderful, 2 reviews
"Wonderful home in a gorgeous area. The house was updated beautifully and clean, spacious deck and the pool was great. We really loved our time there and would stay again! Host was responsive and easy to work with as well :)"
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
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Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, 6 reviews
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
10.0 out of 10, Exceptional, 1 review
"Our overall expertise was great. Home was very clean and had all the essentials you need for a nice comfortable stay. The beds were very comfy, equipped with great linens and pillows. Home was cozy and comfortable. Can’t wait to stay again."
The price is NZ$2,897
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, 7 reviews
"The house was great. Super comfortable and the backyard is wonderful with a gas fireplace, a fire pit, a hot tub, a pool, and an outdoor grill setup. There were 7 of us any it was very comfortable. Dave was great and very prompt and helpful if we needed anything. Would definitely come back."
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
10.0 out of 10, Exceptional, 30 reviews
"Spacious comfortable and inviting home. Well-stocked everything. Lovely outdoor spaces and gracious hosts."
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Gorgeous Garden Home with secluded and heated pool, quiet getaway
10.0 out of 10, Exceptional, 7 reviews
"Great pet friendly property in Amagansett! Best feature of the the house has to be the backyard. Large deck around swimming pool, with built-in grill, pergola. The property is completely gated (included a gated entrance) and in a very quite neighborhood. Easy access to shopping and restaurants in Amagansett and short drive to Montauk. Property being managed by StayMarquis was a plus as they were very responsive and met us at the property upon arrival. Finding the house is challenging as Google...
Gorgeous Garden Home with secluded and heated pool, quiet getaway
Lovely Westbrook Home w/ Patio - Walk to Beach!
10.0 out of 10, Exceptional, 1 review
"Beautifully decorated comfortable and clean would definitely rent again"
Lovely Westbrook Home w/ Patio - Walk to Beach!
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 74 reviews
"From the minute I stepped on the property and then went inside, I fell in Love! So tranquil and peaceful, yet you can drive 10 minutes into the heart of it all and experience the reasons East Hampton’s is well known for, and then some! I have never been to a vacation home where I didn’t have to scrub down, clean and or have to pack everything I needed because it was ALL there. The attention to every detail .. I thank Rick for that and he was exceptionally responsive! ( this is my first booking...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Get out of the heat! Amazing home with pool, hot tub, pirate ship and much more!
10.0 out of 10, Exceptional, 70 reviews
"Property is well kept and clean, pool and hot tub were both in well working condition! Plenty of entertainment for the kids and appreciated the plentiful dishware and cooking utensils for big family meals. Owner of the home was very responsive and answered all of our questions. Only call out is I wish the shipyard playground in the backyard was better maintained. The slide covered in spiderwebs and needed to be cleaned."
Get out of the heat! Amazing home with pool, hot tub, pirate ship and much more!
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, 9 reviews
"my family and i grew up coming to hampton bays - and while myself and my parents have moved away - a family wedding brought us back to the area and we were so happy to stay local in this perfect home. it felt great to be back in the old neighborhood and not have to be cramped at my brothers home just a short 5 minute drive away. i hope we can stay again during our next trip!"
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Sun Drenched East Hampton Springs Retreat with Private Beach Pass
Sun Drenched East Hampton Springs Retreat with Private Beach Pass
Cozy Ocean front view, Beach house , lay in bed and hear the waves! Waterford CT
10.0 out of 10, Exceptional, 6 reviews
"The cottage was perfect for us. Beautiful location, easy access to the beach. Beds are very comfortable. Spacious and the sunroom is a wonderful place to sit and relax. My sisters and I thoroughly enjoyed everything about the area. The locals are welcoming and will provide you with great information about the area. Mystic aquarium is within 20 minutes and a great place to visit. There are a multitude of great restaurants to try out and fresh fish markets if you want to grill out in the back...
Cozy Ocean front view, Beach house , lay in bed and hear the waves! Waterford CT
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
9.0 out of 10, Wonderful, 9 reviews
"Great house with everything you need for a fun weekend. Enjoyed the kayaks, deck, view, birds and surrounding area. Host was very welcoming and accommodating."
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Niantic Cottage Minutes from Beach | Play & Relax
10.0 out of 10, Exceptional, 5 reviews
"older cottage style well maintained great area"
Niantic Cottage Minutes from Beach | Play & Relax
1820 Whaling Captain's Home
10.0 out of 10, Exceptional, 47 reviews
"Great property. Great owner."
1820 Whaling Captain's Home
Pristine & Private East Hampton Bungalow
Pristine & Private East Hampton Bungalow
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, 4 reviews
The price is NZ$11,532
includes taxes & fees
2 July - 3 July
2 Jul - 3 Jul
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, 86 reviews
"It was a cute cottage, nicely decorated. We were very comfortable. Each bedroom had a private bathroom which was very nice. It was close to downtown Southampton so that was great. The owner checked in and was very helpful. "
The price is NZ$1,493
includes taxes & fees
26 June - 27 June
26 Jun - 27 Jun
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Shelter Island

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, 1,030 reviews
"Montauk Manor is a beautiful property and very well maintained. The views are spectacular. Monty's restaurant had delicious breakfasts and dinners. The pool was very nice. The accommodations were very clean. The outdoor patio was an added bonus. The staff were very pleasant and helpful."
The price is NZ$766
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 240 reviews
"Access to the beach. "
The price is NZ$668
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.6 out of 10, Excellent, 224 reviews
"Very nice location and nice condo"
The price is NZ$620
includes taxes & fees
24 June - 25 June
24 Jun - 25 Jun
The Surf Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Shelter Island Holiday Homes information

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