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Search Vacation Homes in Shelter Island Heights

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Compare 1662 Vacation Homes in Shelter Island Heights with updated reviews, rates, and availability.

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
9.0 out of 10, Wonderful, (2)
"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!
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"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
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Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, (10)
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
10.0 out of 10, Exceptional, (34)
"Condo was in a great location. Close to all. Well equipped and very comfortable! Excellent host!"
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Lovely Westbrook Home w/ Patio - Walk to Beach!
10.0 out of 10, Exceptional, (1)
"Beautifully decorated comfortable and clean would definitely rent again"
Lovely Westbrook Home w/ Patio - Walk to Beach!
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (51)
"My family and I thoroughly enjoyed our time in Sag Harbor. The home was conveniently located and ideal for our five-day getaway. Daniel was quick to respond and offered excellent recommendations for restaurants and beach spots. The property was beautiful, and the pool provided a tranquil setting. We're eagerly anticipating future trips."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
July 4th in the Hamptons! Amazing home with pool, hot tub, pirate ship and more!
10.0 out of 10, Exceptional, (69)
"We had a wonderful time. A beautiful home and an easy process from booking through check out."
July 4th in the Hamptons! Amazing home with pool, hot tub, pirate ship and more!
The Hampton Sack a cheerful relaxing beach cottage
7.4 out of 10, Good, (12)
"Awesome break away from reality. Hope to return soon!"
The Hampton Sack a cheerful relaxing beach cottage
Modern, updated spacious home. 5 min walk to beach. 1 min to Water's Edge Resort
10.0 out of 10, Exceptional, (43)
"Property was perfect. Very nicely updated and had everything we needed for a great beach getaway. Kevin was extremely responsive when we had questions. Would definitely stay again!"
Modern, updated spacious home. 5 min walk to beach. 1 min to Water's Edge Resort
Unique Modern Barn House in Sag Harbor
10.0 out of 10, Exceptional, (10)
"Beautiful home with separate space for everyone and close to water and town!"
Unique Modern Barn House in Sag Harbor
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, (9)
"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
Niantic Cottage Minutes from Beach | Play & Relax
10.0 out of 10, Exceptional, (4)
"Comfortable house with a well stocked kitchen and convenient laundry. We enjoyed walking to the town and fish market. The train runs between the town and waterfront, entry points are at the far ends of town, at either end of the board walk. Nice quiet neighborhood."
Niantic Cottage Minutes from Beach | Play & Relax
1820 Whaling Captain's Home
10.0 out of 10, Exceptional, (46)
"We stayed at this house for 3 days at the beginning of the season. It’s very close to everything in town and was very thoughtfully designed and maintained. It was absolutely perfect, especially the amazing garden. Highly recommended."
1820 Whaling Captain's Home
Cozy Hamptons Beach House 1 Block from the Beach!
Cozy Hamptons Beach House 1 Block from the Beach!
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (25)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (73)
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Beach House
9.8 out of 10, Exceptional, (45)
"Lovely, well maintained property. Short walk to the shoreline and the neighborhood market (which has great coffee, muffins, shakes, etc). The fenced yard was wonderful for the dogs. Serene and quiet but friendly neighborhood. Excellent communication with property owner and easy check-in/out. Everything was as described on the site and it made for a wonderful weekend getaway!"
Beach House
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, (7)
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (23)
"It was a great weekend"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
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See all available properties in Shelter Island Heights
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 Heights

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1026)
"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 $395
$470 total
includes taxes & fees
Jun 16 - Jun 17
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (240)
"Access to the beach. "
The price is $318
$385 total
includes taxes & fees
Jun 16 - Jun 17
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (223)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $286
$381 total
includes taxes & fees
Jun 24 - Jun 25
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 Heights Vacation Homes information

Number of reviews
437
Accommodation
1662 Vacation Homes
Lowest Price
Highest Price

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