Holiday Homes in Shelter Island

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Shelter Island holiday homes

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 €389
includes taxes & fees
8 Jun - 9 Jun
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
8.8 out of 10, Excellent, (6 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 €374
includes taxes & fees
8 Jun - 9 Jun
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is €352
includes taxes & fees
9 Jun - 10 Jun
Adorable Cottage, 5 min walk to water & town
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, (12 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €390
includes taxes & fees
8 Jun - 9 Jun
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, (59 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Smart TV

Lake House - A

Lake House - A
East Lyme
The price is €474
includes taxes & fees
8 Jun - 9 Jun
Lake House - A
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, (138 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is €522
includes taxes & fees
7 Jun - 8 Jun
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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, (17 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is €1,249
includes taxes & fees
7 Jun - 8 Jun
Black Swan Beachfront Home with Jacuzzi year round
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 €823
includes taxes & fees
1 Jul - 2 Jul
Beachside Bliss w/ Game Room, Gym & Golf Green
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is €742
includes taxes & fees
8 Jun - 9 Jun
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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 €989
includes taxes & fees
8 Jun - 9 Jun
BlackBerry Private home with jacuzzi yearlong
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, (132 reviews)
"Great property!"
United States
Matthew B.
The price is €783
includes taxes & fees
25 Jun - 26 Jun
Coastal New England Waterfront Home, Harkness Park, Casinos
Smart TV

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
East Lyme
9.8 out of 10, Exceptional, (23 reviews)
"I’ve stayed at this property for 3 summers in a row and every time it has been perfect. Lots of room, very clean and a perfect view!"
United States
Elisa N.
The price is €2,128
includes taxes & fees
12 Jun - 13 Jun
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
The price is €539
includes taxes & fees
29 Jun - 30 Jun
Hampton Bays Townhouse - Pool, Beach Access
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 €593
includes taxes & fees
7 Jun - 8 Jun
Northfork Townhouse walk to all
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 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 €529
includes taxes & fees
8 Jun - 9 Jun
Renovated Townhouse walk to all
Terrace/patio

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
9.8 out of 10, Exceptional, (21 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is €733
includes taxes & fees
7 Jun - 8 Jun
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Outdoor pool, a heated pool

Hamptons Tiana Bay Oasis

Hamptons Tiana Bay Oasis
Hampton Bays
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed this newly renovated home and had a wonderful time. Beautiful pool and grounds. "
United States
Anonymous traveller
The price is €1,220
includes taxes & fees
16 Jun - 17 Jun
Hamptons Tiana Bay Oasis
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €276
includes taxes & fees
7 Jun - 8 Jun
American Beech in Greenport - Petite King Room 7
Interior

Breakwater Estate… perfect for Large Group Getaways!

Breakwater Estate… perfect for Large Group Getaways!
Mattituck
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is €1,652
includes taxes & fees
25 Jun - 26 Jun
Breakwater Estate… perfect for Large Group Getaways!
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

Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Great Experience! Friendly staff Extremely comfortable"
Rue 1-night trip
Posted less than an hour ago
Ocean Resort Inn

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
495
Accommodation
1700 Holiday Homes
Lowest Price
€276
Highest Price
€2,128