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Holiday Homes in Shelter Island

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Featured Holiday Homes in Shelter Island

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (52)
"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "
The price is AU$2,243
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount

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 AU$563
includes taxes & fees
3 Nov - 4 Nov
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 AU$626
includes taxes & fees
14 Oct - 15 Oct
Rogers Lake House (87) · CT College+Beach+USCGA

Insta-worthy Couples Retreat: Perfect for romantic getaway!

9.6 out of 10, Exceptional, (51)
"Great stay, charming cottage, hope to return"
The price is AU$414
includes taxes & fees
13 Oct - 14 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
The price is AU$1,416
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 AU$634
includes taxes & fees
13 Oct - 14 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is AU$10,112
includes taxes & fees
16 Oct - 17 Oct
Spacious 5-bedroom house with water views and 2 houses from the bay.

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 AU$2,071
includes taxes & fees
14 Oct - 15 Oct
Private completely fenced in property. Near beach

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 AU$9,168
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is AU$478
includes taxes & fees
13 Oct - 14 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 AU$961
includes taxes & fees
13 Oct - 14 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

Lake House - A

2.0 star property
The price is AU$777
includes taxes & fees
16 Oct - 17 Oct
Lake House - A

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 AU$2,405
includes taxes & fees
20 Oct - 21 Oct
Private beach on a fenced in property sunset views

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 AU$908
includes taxes & fees
13 Oct - 14 Oct
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Sag Harbor Water View w Dock 1.5ml from town

The price is AU$9,866
includes taxes & fees
14 Oct - 15 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 AU$5,471
includes taxes & fees
20 Oct - 21 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

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 AU$1,060
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 AU$1,809
includes taxes & fees
13 Oct - 14 Oct
Beautifully farmhouse

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."
The price is AU$1,641
includes taxes & fees
13 Oct - 14 Oct
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 Hotel Reviews

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Shelter Island Holiday Homes information

Number of reviews
393
Accommodation
1993 Holiday Homes
Lowest Price
AU$414
Highest Price
AU$10,112