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Holiday Homes in Shelter Island Heights

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Featured Holiday Homes in Shelter Island Heights and around

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (9)
"Open concept home beautiful with private yard space. It was perfect for our stay"
The price is €318
includes taxes & fees
30 Oct - 31 Oct
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (2)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
The price is €355
includes taxes & fees
15 Oct - 16 Oct
Rogers Lake House (87) · CT College+Beach+USCGA
Insta-worthy Couples Retreat: Perfect for romantic getaway!
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
The price is €236
includes taxes & fees
14 Oct - 15 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Spacious 5-bedroom house with water views and 2 houses from the bay.
The price is €5,739
includes taxes & fees
24 Oct - 25 Oct
Spacious 5-bedroom house with water views and 2 houses from the bay.
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is €5,123
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
Cozy quiet gem, private & fenced in backyard
9.4 out of 10, Exceptional, (3)
"good times"
The price is €800
includes taxes & fees
16 Oct - 17 Oct
Cozy quiet gem, private & fenced in backyard
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is €358
includes taxes & fees
14 Oct - 15 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Private completely fenced in property. Near beach
9.6 out of 10, Exceptional, (22)
"The place is in nice neighborhood and private entrance. It has all the amenities for a good staying. Definitely will stay again in the future."
The price is €1,169
includes taxes & fees
14 Oct - 15 Oct
Private completely fenced in property. Near beach
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"Great job "
The price is €270
includes taxes & fees
14 Oct - 15 Oct
American Beech in Greenport - Petite King Room 7
Coastal New England Waterfront Home, Harkness Park, Casinos
10.0 out of 10, Exceptional, (123)
"Repeat renter! Great location, super clean house, A host: very responsive; will be back again! "
The price is €485
includes taxes & fees
14 Oct - 15 Oct
Coastal New England Waterfront Home, Harkness Park, Casinos
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
10.0 out of 10, Exceptional, (1)
"We were escaping NYC for the weekend and exploring real estate in the area. This house was absolutely beautiful and way bigger than we needed. Unfortunately it was rainy out and we really didn’t get to spend too much time in the house since we were driving around it looks like it has a beautiful property with a pool etc. so hopefully we can come back in the summer."
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
Sag Harbor Water View w Dock 1.5ml from town
The price is €5,640
includes taxes & fees
16 Oct - 17 Oct
Sag Harbor Water View w Dock 1.5ml from town
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
10.0 out of 10, Exceptional, (44)
"Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. "
The price is €3,091
includes taxes & fees
20 Oct - 21 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (133)
"Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend."
The price is €513
includes taxes & fees
26 Oct - 27 Oct
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Private beach on a fenced in property sunset views
10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
The price is €1,339
includes taxes & fees
20 Oct - 21 Oct
Private beach on a fenced in property sunset views
Lake House - A
2.0 star property
The price is €439
includes taxes & fees
14 Oct - 15 Oct
Lake House - A
Charming Northfork Townhouse- walk to all
10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
The price is €588
includes taxes & fees
15 Oct - 16 Oct
Charming Northfork Townhouse- walk to all
Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
The price is €1,036
includes taxes & fees
12 Nov - 13 Nov
Beautifully farmhouse
Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
The price is €174
includes taxes & fees
12 Nov - 13 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
Village gem walk to Main Street fenced in property
9.2 out of 10, Wonderful, (5)
"Second year at this lovely house for the 4th of July extended weekend. The hosts are responsive and helpful, and the house is exactly what you need for 2-3 people. Very clean, nicely decorated, kitchen was nicely stocked. It is in a great location. Easily able to walk into town for shopping or dining."
Village gem walk to Main Street fenced in property
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.
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Top Shelter Island Heights Hotel Reviews

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Shelter Island Heights Holiday Homes information

Number of reviews
341
Accommodation
1880 Holiday Homes
Lowest Price
€236
Highest Price
€5,739