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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 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 £330
includes taxes & fees
19 May - 20 May
Rogers Lake House (87) · CT College+Beach+USCGA
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, (56 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is £205
includes taxes & fees
19 May - 20 May
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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 £312
includes taxes & fees
20 May - 21 May
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is £335
includes taxes & fees
19 May - 20 May
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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 £363
includes taxes & fees
19 May - 20 May
Adorable Cottage, 5 min walk to water & town
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.2 out of 10, Wonderful, (5 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 £337
includes taxes & fees
21 May - 22 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
The price is £459
includes taxes & fees
5 Jun - 6 Jun
#35 - Beautiful 3 BR Beach Haven
Dining

Summer is filling up-Beach, Shopping and Golf

Summer is filling up-Beach, Shopping and Golf
Clinton
10.0 out of 10, Exceptional, (4 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
Summer is filling up-Beach, Shopping and Golf
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 £239
includes taxes & fees
21 May - 22 May
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)
"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 £1,102
includes taxes & fees
26 May - 27 May
Black Swan Beachfront Home with Jacuzzi year round
Smart TV

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
Waterford
10.0 out of 10, Exceptional, (5 reviews)
"Great location and extremely clean. I would definitely recommend and stay again. "
United States
Zach S.
The price is £350
includes taxes & fees
26 May - 27 May
Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
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 £452
includes taxes & fees
19 May - 20 May
Beachside Bliss w/ Game Room, Gym & Golf Green
Dining

Designer East Hampton Farmhouse - Bike to Amagansett, Ocean Beaches, Pool Open

Designer East Hampton Farmhouse - Bike to Amagansett, Ocean Beaches, Pool Open
East Hampton North
Designer East Hampton Farmhouse - Bike to Amagansett, Ocean Beaches, Pool Open
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.
Northfork Townhouse walk to all
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.8 out of 10, Exceptional, (11 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 £524
includes taxes & fees
20 May - 21 May
Renovated Townhouse walk to all
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 £958
includes taxes & fees
20 May - 21 May
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, (137 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 £518
includes taxes & fees
20 May - 21 May
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Smart TV

Lake House - A

Lake House - A
East Lyme
The price is £433
includes taxes & fees
1 Jun - 2 Jun
Lake House - A
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
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.
The price is £769
includes taxes & fees
19 May - 20 May
Beachfront Greenport Villa
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, (24 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £1,464
includes taxes & fees
21 May - 22 May
Villa Luz Cozy Family Home with Jacuzzi year round
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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Our stay was excellent and the room exceeded our expectations. I wish we'd stay longer."
Christy 1-night trip
Posted 2 hours ago
Beachcomber Resort at Montauk

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
316
Accommodation
1708 Holiday Homes
Lowest Price
£205
Highest Price
£1,464