A pebbled beach with a sunset and a distant bridge.

Holiday Homes in Shelter Island Heights

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Shelter Island Heights holiday homes

Sun-loungers, beach towels

1. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is AU$525
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
Sun-loungers, beach towels

2. 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 AU$525
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
Sun-loungers, beach towels

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, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$702
includes taxes & fees
15 Sept - 16 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Terrace/patio

4. 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 AU$613
includes taxes & fees
7 Sept - 8 Sept
American Beech in Greenport - Petite King Room 7
Beach

5. 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 AU$748
includes taxes & fees
8 Sept - 9 Sept
Beach Block Hideaway
Coffee/tea maker, fridge, microwave, oven

6. 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 AU$2,000
includes taxes & fees
15 Sept - 16 Sept
Work and Play Special! Extended Stay Discount
Property grounds

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 AU$700
includes taxes & fees
7 Sept - 8 Sept
American Beech in Greenport - Deluxe King 6
Property grounds

8. 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 AU$2,040
includes taxes & fees
10 Sept - 11 Sept
Beachfront Greenport Villa
Property grounds

9. 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 AU$818
includes taxes & fees
13 Sept - 14 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Beach nearby

10. 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 AU$434
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Interior

11. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is AU$1,979
includes taxes & fees
13 Sept - 14 Sept
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Beach nearby

12. 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 AU$615
includes taxes & fees
9 Sept - 10 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Exterior detail

13. 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.
The price is AU$600
includes taxes & fees
2 Sept - 3 Sept
Lake House—Unit B
Smart TV, fireplace, books

14. 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 AU$667
includes taxes & fees
2 Sept - 3 Sept
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
TV, fireplace, books, stereo

15. 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 AU$2,076
includes taxes & fees
13 Sept - 14 Sept
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
Dining

16. Summer is filling up-Beach, Shopping and Golf

Summer is filling up-Beach, Shopping and Golf
Clinton
10.0 out of 10, Exceptional, (5 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 AU$997
includes taxes & fees
18 Aug - 19 Aug
Summer is filling up-Beach, Shopping and Golf
Outdoor dining

17. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (31 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is AU$761
includes taxes & fees
24 Aug - 25 Aug
Lakeside Bliss
Beach

18. 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 AU$1,054
includes taxes & fees
9 Sept - 10 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

19. 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 AU$949
includes taxes & fees
31 Aug - 1 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Beach nearby, sun-loungers, beach towels

20. 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 AU$1,418
includes taxes & fees
14 Sept - 15 Sept
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
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 Heights Hotel Reviews

Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Simple but tastefully updated rooms with a bonus ocean view! Had everything we needed to make our stay in Montauk wonderful Great location Spotless and well maintained grounds Very nice pool and lounging areas"
Lewis 3-night trip
Posted 21 hours ago
Ocean Resort Inn

Find out more about Shelter Island Heights

Shelter Island Heights Holiday Homes information

Number of reviews
2,534
Accommodation
1346 Holiday Homes
Lowest Price
AU$128
Highest Price
AU$923