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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Shelter Island holiday homes

Smart TV, fireplace, books

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is £322
includes taxes & fees
7 Apr - 8 Apr
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (53 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is £158
includes taxes & fees
7 Apr - 8 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Smart TV, books

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 £327
includes taxes & fees
8 Apr - 9 Apr
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

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 £328
includes taxes & fees
7 Apr - 8 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Property grounds

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 £201
includes taxes & fees
5 Apr - 6 Apr
Stylish Modern Stay Steps from the Ocean
Outdoor dining

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (126 reviews)
"Great property!"
United States
Matthew B.
The price is £474
includes taxes & fees
24 Apr - 25 Apr
Coastal New England Waterfront Home, Harkness Park, Casinos
Living area

Newly Renovated Sag Harbor Beach House with Pool

Newly Renovated Sag Harbor Beach House with Pool
Sag Harbor
The price is £555
includes taxes & fees
6 Apr - 7 Apr
Newly Renovated Sag Harbor Beach House with Pool
Beach

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 £389
includes taxes & fees
14 Apr - 15 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

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 £198
includes taxes & fees
5 Apr - 6 Apr
American Beech in Greenport - Petite King Room 7
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is £817
includes taxes & fees
8 Apr - 9 Apr
Black Swan Beachfront Home with Jacuzzi year round
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is £599
includes taxes & fees
5 Apr - 6 Apr
BlackBerry Private home with jacuzzi yearlong
Interior

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 £432
includes taxes & fees
3 Apr - 4 Apr
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Smart TV, fireplace

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 £450
includes taxes & fees
6 Apr - 7 Apr
Renovated Townhouse walk to all
Outdoor dining

Villa Luz Cozy Family Home with Jacuzzi year round

Villa Luz Cozy Family Home with Jacuzzi year round
Hampon Bays
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £642
includes taxes & fees
3 Apr - 4 Apr
Villa Luz Cozy Family Home with Jacuzzi year round
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is £825
includes taxes & fees
8 Apr - 9 Apr
Minutes from the beach, brand new 4 bedroom
Dining

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 £509
includes taxes & fees
3 Apr - 4 Apr
Northfork Townhouse walk to all
Interior

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 £966
includes taxes & fees
16 Apr - 17 Apr
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is £1,454
includes taxes & fees
3 Apr - 4 Apr
Cozy 5 Bedroom With Wi-fi And Air Condition
Interior

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 £2,155
includes taxes & fees
5 Apr - 6 Apr
Sag Harbor Water View w Dock 1.5ml from town
Smart TV, fireplace, ping pong, books

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 £4,104
includes taxes & fees
3 Apr - 4 Apr
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

Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only

6/10 Okay
"We were unhappy with two aspects. The shower is extremely small -- about 2 feet by 3 feet. Very tight. I personally would rip out the closet next to it in a heartbeat and enlarge the shower. The TV was also difficult to figure out and the staff on duty at the desk was unable to assist. Breakfast was fine, just monotonous -- it was always bagels, which isn't great with no toaster to toast them in."
Murray 4-night trip
Posted 2 hours ago
Aqua by American Beech - Adults Only

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
363
Accommodation
1792 Holiday Homes
Lowest Price
£158
Highest Price
£4,104