Search Residences in Shelter Island Heights from CA $120

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island Heights

A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

1. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (78 reviews)
"We enjoyed our stay!"
Australia
Nicholas
The price is CA $240
CA $274 total
includes taxes & fees
Nov 19 - Nov 20
The Chequit
A two-story white house with a porch and an American flag.

2. Seven - A Resort Style Inn

Seven - A Resort Style Inn
2.0 star property
Shelter Island Heights
The price is CA $538
CA $614 total
includes taxes & fees
Nov 24 - Nov 25
Seven - A Resort Style Inn
A sign for 'House on Chase Creek' with a view of a lake and trees in the background.

3. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is CA $261
CA $298 total
includes taxes & fees
Nov 10 - Nov 11
House on Chase Creek
A beachside outdoor seating area with white Adirondack chairs and a fire pit.

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (191 reviews)
"Nicely renovated and enjoyable."
United States
Becky
The price is CA $274
CA $313 total
includes taxes & fees
Dec 10 - Dec 11
Silver Sands Motel & Beach Bungalows
A two-story house with a balcony, outdoor seating area, and a variety of plants.

5. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (446 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is CA $192
CA $220 total
includes taxes & fees
Nov 17 - Nov 18
Zey Hotel
The entrance to The Harbor Front Inn with a double door and the address number 209.

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (675 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
The price is CA $193
CA $261 total
includes taxes & fees
Nov 15 - Nov 16
The Harbor Front Inn
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

7. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (196 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is CA $347
CA $460 total
includes taxes & fees
Dec 9 - Dec 10
The Menhaden
A cozy interior with a bar area, seating, and a fireplace.

8. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
"convenient location, clean & updated room. great stay :)"
United States
Jacqueline
The price is CA $266
CA $335 total
includes taxes & fees
Nov 15 - Nov 16
Oyster Estate
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

9. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (350 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is CA $262
CA $335 total
includes taxes & fees
Nov 10 - Nov 11
The Shoals Suites and Slips
A spacious room with wicker furniture, large windows, and a view of the sea.

10. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (767 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is CA $215
CA $286 total
includes taxes & fees
Nov 24 - Nov 25
Sound View Greenport
A balcony with a view of the ocean, a lawn, and a house in the background.

11. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $271
CA $467 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
A modern interior with a central water feature, shelves with products, and a clothing rack.

12. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is CA $354
CA $461 total
includes taxes & fees
Nov 12 - Nov 13
American Beech Hotel
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

13. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is CA $134
CA $342 total
includes taxes & fees
Nov 18 - Nov 19
Aqua Vista
A marina with several boats docked, including a white boat with "PECONIC STAR" written on it.

14. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is CA $121
CA $322 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper
A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

15. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is CA $121
CA $322 total
includes taxes & fees
Nov 15 - Nov 16
Harbor Heights
A modern house with a deck, outdoor seating, and a fire pit.

16. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is CA $436
CA $498 total
includes taxes & fees
Nov 17 - Nov 18
North Fork Resort
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

17. 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, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is CA $184
CA $492 total
includes taxes & fees
Nov 10 - Nov 11
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

18. 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 CA $276
CA $605 total
includes taxes & fees
Nov 11 - Nov 12
Beach Block Hideaway
A modern interior with a central water feature, shelves with products, and a clothing rack.

19. American Beech in Greenport NY - King Suite 1

American Beech in Greenport NY - King Suite 1
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Perfect Great place"
United States
Dean J.
The price is CA $295
CA $428 total
includes taxes & fees
Nov 12 - Nov 13
American Beech in Greenport NY - King Suite 1
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

20. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (687 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is CA $309
CA $353 total
includes taxes & fees
Nov 10 - Nov 11
Sag Harbor Inn
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.
View all properties

Learn more about Shelter Island Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

See all hotels in Shelter Island Heights
A pebbled beach with a sunset and a distant bridge.

Top reviews in Shelter Island Heights

A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.
The Chequit

The Chequit

The Chequit
The Heights

10/10 Excellent

Absolutely beautiful! I really hope to be back there again soon!
Canada
Peter
Reviewed September 1, 2024
The Chequit

Explore a world of travel with Expedia