Holiday Homes in Shelter Island

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Our top choices for Shelter Island holiday homes

10.0 out of 10, Exceptional, (11 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €327
includes taxes & fees
5 Mar - 6 Mar
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (5 reviews)
"Communication was excellent. "
United States
Katy C.
The price is €401
includes taxes & fees
8 Mar - 9 Mar
Rogers Lake House (87) · CT College+Beach+USCGA
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is €413
includes taxes & fees
5 Mar - 6 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €174
includes taxes & fees
17 Mar - 18 Mar
American Beech in Greenport - Petite King Room 7
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is €307
includes taxes & fees
5 Mar - 6 Mar
Stylish Modern Stay Steps from the Ocean
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is €458
includes taxes & fees
11 Mar - 12 Mar
Beachside Bliss w/ Game Room, Gym & Golf Green

Holiday Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is €547
includes taxes & fees
5 Mar - 6 Mar
Immaculate Waterfront 2 bedroom!

Holiday Home in Greenport

Northfork Townhouse walk to all
10.0 out of 10, Exceptional, (5 reviews)
"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"
United States
Beth R.
The price is €508
includes taxes & fees
5 Mar - 6 Mar
Northfork Townhouse walk to all

Holiday Home in Greenport

Renovated Townhouse walk to all
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is €493
includes taxes & fees
5 Mar - 6 Mar
Renovated Townhouse walk to all

Holiday Home in Greenport

Beachfront Greenport Villa
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
Beachfront Greenport Villa
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is €941
includes taxes & fees
15 Mar - 16 Mar
Minutes from the beach, brand new 4 bedroom
The price is €1,660
includes taxes & fees
15 Mar - 16 Mar
Cozy 5 Bedroom With Wi-fi And Air Condition
10.0 out of 10, Exceptional, (1 review)
The price is €720
includes taxes & fees
23 Mar - 24 Mar
Beach cottage, private road, private beach, private mooring, private parking.
9.2 out of 10, Wonderful, (11 reviews)
"Great location. Great host. Easy house, pool and private back yard. It's modest but has it all."
United States
Harry V.
The price is €966
includes taxes & fees
15 Mar - 16 Mar
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is €4,684
includes taxes & fees
5 Mar - 6 Mar
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
The price is €1,949
includes taxes & fees
10 Mar - 11 Mar
Sag Harbor Water View w Dock 1.5ml from town
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is €1,335
includes taxes & fees
5 Mar - 6 Mar
Cozy Hamptons Escape 3BR Minutes From Beach!
The price is €5,612
includes taxes & fees
8 Mar - 9 Mar
Spacious 5-bedroom house with water views and 2 houses from the bay.
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

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
77
Accommodation
1792 Holiday Homes
Lowest Price
€174
Highest Price
€5,612