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Holiday Homes in Shelter Island

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Our top choices for Shelter Island holiday homes

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 NZ$2,208
includes taxes & fees
16 Sept - 17 Sept
Work and Play Special! Extended Stay Discount

2. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is NZ$709
includes taxes & fees
14 Sept - 15 Sept
Beach Block Hideaway

3. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is NZ$722
includes taxes & fees
8 Sept - 9 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is NZ$602
includes taxes & fees
10 Sept - 11 Sept
The SandPiper

5. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is NZ$641
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista

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 NZ$596
includes taxes & fees
16 Sept - 17 Sept
American Beech in Greenport - Petite King Room 7

7. 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 NZ$1,359
includes taxes & fees
9 Sept - 10 Sept
Northfork Townhouse walk to all

8. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (13 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.
Renovated Townhouse walk to all

9. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
Beachfront Greenport Villa

10. 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 NZ$956
includes taxes & fees
29 Sept - 30 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

11. 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 NZ$740
includes taxes & fees
17 Sept - 18 Sept
American Beech in Greenport - Deluxe King 6

12. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 NZ$2,810
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong

13. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, 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 NZ$2,131
includes taxes & fees
13 Sept - 14 Sept
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

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, (1 review)
"Great clean beautiful property."
United States
ANGELA S.
The price is NZ$2,020
includes taxes & fees
27 Sept - 28 Sept
Spacious house in East Hampton with heated pool + WFH

15. 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 NZ$496
includes taxes & fees
30 Sept - 1 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!

16. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"It was close to a very pretty beach, which was nice. The neighborhood is very quiet. The only downside was that the bedrooms were up stairs and the stairs were very steep. I didn’t notice that in the write up to the property it might have changed my rental of it. I would rate it very highly for anyone that doesn’t have trouble with stairs. The air conditioning was excellent, and the property is well appointed the owners were lovely and responsive."
United States
Sandra Hart
The price is NZ$843
includes taxes & fees
9 Sept - 10 Sept
Adorable Cottage, 5 min walk to water & town

17. 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 NZ$733
includes taxes & fees
16 Sept - 17 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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 NZ$853
includes taxes & fees
10 Sept - 11 Sept
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

19. Lake House—Unit B

Lake House—Unit B
East Lyme
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay in Niantic! The home was spotless, quiet, and felt so fresh the moment we walked in. (Clean and fresh is a must for me and everything was met!) The location couldn’t have been better; just a short walk to the ocean/boardwalk and close to downtown shops and restaurants. It was the perfect relaxing getaway. Loved our time here and will absolutely be back again!”"
United States
Jennifer C.
Lake House—Unit B

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 NZ$1,072
includes taxes & fees
10 Sept - 11 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

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
345
Accommodation
1292 Holiday Homes
Lowest Price
NZ$496
Highest Price
NZ$2,810