A wooden gazebo by a pond with a large tree trunk nearby.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Shelter Island holiday homes

A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

1. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is £1,059
includes taxes & fees
16 Sept - 17 Sept
Work and Play Special! Extended Stay Discount
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

2. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (48 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is £288
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

3. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is £288
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
A wooden pathway leading to a beach with scattered rocks and greenery.

4. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
The price is £400
includes taxes & fees
14 Sept - 15 Sept
Beach Block Hideaway
A beach with people relaxing, a pier extending into the water, and a clear sky.

5. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is £378
includes taxes & fees
7 Sept - 8 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

6. 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)
"Great place! So nice."
United States
Paul F.
The price is £329
includes taxes & fees
7 Sept - 8 Sept
American Beech in Greenport - Petite King Room 7
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

7. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is £507
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all
A modern dining area with a wooden table, white chairs, and a chandelier.

8. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 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 £718
includes taxes & fees
17 Sept - 18 Sept
Northfork Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

9. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is £1,110
includes taxes & fees
10 Sept - 11 Sept
Beachfront Greenport Villa
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

10. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is £368
includes taxes & fees
8 Sept - 9 Sept
American Beech in Greenport - Deluxe King 6
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

11. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is £438
includes taxes & fees
13 Sept - 14 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is £1,294
includes taxes & fees
23 Aug - 24 Aug
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A stone pier leading to a beach with houses in the background.

13. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is £211
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

14. East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (2 reviews)
"We have just returned from an amazing summer experience in East Hampton! From the minute I secured the booking to checkout, everything was perfectly smooth! The house was so wonderful, every design detail and amenity…. It was truly like the best of all possible creature comforts…. Fully stocked kitchen, incredible fire pit for late evening s’mores, extraordinary huge pool, patio with outdoor speakers, and enough indoor space meticulously designed and decorated that proved our dream vacation...
United States
GINA W.
The price is £1,019
includes taxes & fees
16 Sept - 17 Sept
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

15. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (7 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 £323
includes taxes & fees
15 Sept - 16 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

16. 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 £532
includes taxes & fees
15 Sept - 16 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

17. 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, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is £448
includes taxes & fees
31 Aug - 1 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A living room with a fireplace, a grey armchair, and a large window.

18. 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, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is £358
includes taxes & fees
15 Sept - 16 Sept
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A sandy beach with footprints leading to the water, a wooden bench, and a pair of shoes on the ground.

19. Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is £753
includes taxes & fees
14 Sept - 15 Sept
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

20. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 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.
The price is £577
includes taxes & fees
9 Sept - 10 Sept
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Beautiful place"
Annmarie 1-night trip
Posted 1 hour ago
Montauk Yacht Club

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
452
Accommodation
1633 Holiday Homes
Lowest Price
£211
Highest Price
£1,294