Holiday Homes in Shelter Island

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Our top choices for Shelter Island holiday homes

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is €1,129
includes taxes & fees
25 Apr - 26 Apr
Work and Play Special! Extended Stay Discount

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is €232
includes taxes & fees
26 Apr - 27 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is €390
includes taxes & fees
5 May - 6 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is €440
includes taxes & fees
11 May - 12 May
Rogers Lake House (87) · CT College+Beach+USCGA

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
East Hampton North
The price is €863
includes taxes & fees
28 Apr - 29 Apr
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (127 reviews)
"Great property!"
United States
Matthew B.
The price is €505
includes taxes & fees
24 Apr - 25 Apr
Coastal New England Waterfront Home, Harkness Park, Casinos

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
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 €526
includes taxes & fees
28 Apr - 29 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €227
includes taxes & fees
23 Apr - 24 Apr
American Beech in Greenport - Petite King Room 7

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
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 €243
includes taxes & fees
25 Apr - 26 Apr
Stylish Modern Stay Steps from the Ocean

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
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 €501
includes taxes & fees
22 Apr - 23 Apr
Northfork Townhouse walk to all

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening. "
United States
Karen B.
The price is €492
includes taxes & fees
22 Apr - 23 Apr
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
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 €505
includes taxes & fees
22 Apr - 23 Apr
Renovated Townhouse walk to all

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is €1,182
includes taxes & fees
22 Apr - 23 Apr
Minutes from the beach, brand new 4 bedroom

East Hampton Estate for 10, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
East Hampton Estate for 10, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
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 €4,643
includes taxes & fees
25 Apr - 26 Apr
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
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 €773
includes taxes & fees
22 Apr - 23 Apr
Cozy Hamptons Escape 3BR Minutes From Beach!

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is €2,433
includes taxes & fees
27 Apr - 28 Apr
Sag Harbor Water View w Dock 1.5ml from town

Waterfront tranquility near Sag Harbor Village

Waterfront tranquility near Sag Harbor Village
Bay Point
The price is €1,083
includes taxes & fees
23 Apr - 24 Apr
Waterfront tranquility near Sag Harbor Village

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is €1,488
includes taxes & fees
27 Apr - 28 Apr
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is €1,420
includes taxes & fees
7 May - 8 May
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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
438
Accommodation
1698 Holiday Homes
Lowest Price
€227
Highest Price
€4,643