Holiday Homes in Shelter Island

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 June - 28 June

Our top choices for Shelter Island holiday homes

2 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Old Lyme

#34- Stunning-Newly Remodeled
The price is AU$540
includes taxes & fees
6 Mar - 7 Mar
#34- Stunning-Newly Remodeled
Smart TV, fireplace, books

Holiday Home in Waterford

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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 AU$544
includes taxes & fees
9 Mar - 10 Mar
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Smart TV, books

Holiday Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5 reviews)
"Communication was excellent. "
United States
Katy C.
The price is AU$648
includes taxes & fees
8 Mar - 9 Mar
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV, fireplace, books, offices

Holiday Home in Old Saybrook

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is AU$625
includes taxes & fees
6 Mar - 7 Mar
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Dining

Holiday Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
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 AU$678
includes taxes & fees
6 Mar - 7 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Dining

Holiday Home in East Hampton North

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
The price is AU$998
includes taxes & fees
15 Mar - 16 Mar
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
Beach nearby

Holiday Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
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 AU$708
includes taxes & fees
1 Apr - 2 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Property grounds

Holiday Home in Clinton

Stylish Modern Stay Steps from the Ocean
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 AU$477
includes taxes & fees
6 Mar - 7 Mar
Stylish Modern Stay Steps from the Ocean
Beach

Holiday Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
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 AU$771
includes taxes & fees
11 Mar - 12 Mar
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

Holiday Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$284
includes taxes & fees
8 Mar - 9 Mar
American Beech in Greenport - Petite King Room 7
Smart TV, fireplace

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 AU$847
includes taxes & fees
9 Mar - 10 Mar
Renovated Townhouse walk to all
Dining

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 AU$852
includes taxes & fees
6 Mar - 7 Mar
Northfork Townhouse walk to all
Dining

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 AU$903
includes taxes & fees
8 Mar - 9 Mar
Immaculate Waterfront 2 bedroom!
Outdoor dining

Holiday Home in Waterford

Coastal New England Waterfront Home, Harkness Park, Casinos
10.0 out of 10, Exceptional, (126 reviews)
"Great property!"
United States
Matthew B.
The price is AU$758
includes taxes & fees
19 Mar - 20 Mar
Coastal New England Waterfront Home, Harkness Park, Casinos
Smart TV, fireplace, stereo

Holiday Home in Southampton

Minutes from the beach, brand new 4 bedroom
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is AU$1,520
includes taxes & fees
8 Mar - 9 Mar
Minutes from the beach, brand new 4 bedroom
Interior

Holiday Home in Southampton

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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 AU$1,564
includes taxes & fees
13 Mar - 14 Mar
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Interior

Holiday Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town
The price is AU$3,158
includes taxes & fees
16 Mar - 17 Mar
Sag Harbor Water View w Dock 1.5ml from town
Living area

Holiday Home in Wainscott

Cozy 5 Bedroom With Wi-fi And Air Condition
The price is AU$2,690
includes taxes & fees
6 Mar - 7 Mar
Cozy 5 Bedroom With Wi-fi And Air Condition
On the beach, sun-loungers, beach towels

Holiday Home in Laurel

Beach cottage, private road, private beach, private mooring, private parking.
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,155
includes taxes & fees
23 Mar - 24 Mar
Beach cottage, private road, private beach, private mooring, private parking.
Smart TV, fireplace, ping pong, books

Holiday Home in Water Mill

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
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 AU$7,508
includes taxes & fees
6 Mar - 7 Mar
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly disappointed to get a call on our check In day to tell us the indoor pool could not be used. That was literally what we wanted to do for the weekend was relax at the pool and eat and drink. I booked the trips weeks prior so to get a call the day of saying we can’t use to pool during our stay was truly disappointing. They waived the resort fee for the inconvenience, otherwise the weekend was great. "
Tiffany 2-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
200
Accommodation
1611 Holiday Homes
Lowest Price
AU$284
Highest Price
AU$7,508