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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Shelter Island holiday homes

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

1. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is £190
includes taxes & fees
2 Nov - 3 Nov
The SandPiper
A beach with people relaxing, a pier extending into the water, and a clear sky.

2. 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, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is £290
includes taxes & fees
1 Nov - 2 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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, (48 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is £242
includes taxes & fees
7 Oct - 8 Oct
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, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is £330
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
An outdoor dining area with hanging lights, palm trees, and a bar.

5. 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 £235
includes taxes & fees
8 Oct - 9 Oct
American Beech in Greenport - Petite King Room 7
A modern dining area with a wooden table, white chairs, and a chandelier.

6. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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 £482
includes taxes & fees
2 Nov - 3 Nov
Northfork Townhouse walk to all
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

7. 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 £264
includes taxes & fees
6 Oct - 7 Oct
American Beech in Greenport - Deluxe King 6
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.

8. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"We enjoyed the location of the property, and the check-in process was easy and well-organized. The kitchen and bathrooms were clean and nicely appointed. While the space has a lot of potential, there were a few aspects that could be improved. The sofa and upholstered chair were in need of a deep clean, and the sofa cushions had lost their support, making them uncomfortable to use. We could also hear quite a bit of noise from the neighboring unit, and on one night the tenants were active until...
United States
Peggy N.
The price is £469
includes taxes & fees
2 Nov - 3 Nov
Renovated Townhouse walk to all
A dining area with a round table, six chairs, and a chandelier.

9. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
East Hampton
9.2 out of 10, Wonderful, (7 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 £965
includes taxes & fees
6 Oct - 7 Oct
Year round Jacuzzi - Blackberry Home
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

10. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is £863
includes taxes & fees
3 Nov - 4 Nov
Beachfront Greenport Villa
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

11. 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 £842
includes taxes & fees
6 Oct - 7 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

12. 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 £441
includes taxes & fees
1 Nov - 2 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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, (62 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
8 Oct - 9 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

14. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is £804
includes taxes & fees
19 Oct - 20 Oct
Spacious house in East Hampton with heated pool + WFH
A modern building with large windows overlooking a beach.

15. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is £906
includes taxes & fees
6 Oct - 7 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

16. 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 £430
includes taxes & fees
6 Oct - 7 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

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

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable. Did not use any property amenities. Loved the location. A lot of thought in making the property very welcoming. "
United States
Gene E.
The price is £347
includes taxes & fees
8 Oct - 9 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

18. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is £1,647
includes taxes & fees
6 Oct - 7 Oct
Lovely & Spacious Sag Harbor escape with heated pool
A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

19. 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 £298
includes taxes & fees
6 Oct - 7 Oct
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A living room with a fireplace, a grey armchair, and a large window.

20. 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 £364
includes taxes & fees
4 Nov - 5 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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
"Montauk Yacht Club was the perfect getaway for my boyfriend and I to celebrate our 3 year anniversary. Our room was spotless and had a great view of the water. We did mention to them ahead of time that it was our anniversary, thinking they might have some champagne or something waiting in the room for us, but they did not. Nonetheless, it was still a perfect stay. We played tennis and the courts were beautiful. The on-site restaurant was very yummy as well! I definitely recommend coming during the off season, as it is way less crowded in town and very relaxing."
Sarah 3-night trip
Posted 5 hours ago
Montauk Yacht Club

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
275
Accommodation
1311 Holiday Homes
Lowest Price
£190
Highest Price
£1,647