A pebbled beach with a sunset and a distant bridge.

Search Chalets in Shelter Island Heights from CA $261

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island Heights

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 $255
CA $292 total
includes taxes & fees
Nov 22 - Nov 23
The Chequit

2. 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 26 - Nov 27
House on Chase Creek

3. 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

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (192 reviews)
"We loved our stay at Silver Sands! It was off season, so very quiet."
United States
Michael
The price is CA $292
CA $334 total
includes taxes & fees
Dec 6 - Dec 7
Silver Sands Motel & Beach Bungalows

5. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (447 reviews)
"Great place to stay for a walkable visit to Greenport NY. Comfy bed, great rooms for hanging out, close to everything."
United States
JoAnn
The price is CA $229
CA $261 total
includes taxes & fees
Nov 15 - Nov 16
Zey Hotel

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 $195
CA $263 total
includes taxes & fees
Nov 15 - Nov 16
The Harbor Front Inn

7. 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 $254
CA $320 total
includes taxes & fees
Dec 3 - Dec 4
Oyster Estate

8. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (768 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is CA $239
CA $313 total
includes taxes & fees
Nov 30 - Dec 1
Sound View Greenport

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 15 - Nov 16
The Shoals Suites and Slips

10. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (197 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 10 - Dec 11
The Menhaden

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

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 $339
CA $444 total
includes taxes & fees
Nov 22 - Nov 23
American Beech Hotel

13. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is CA $134
CA $326 total
includes taxes & fees
Dec 7 - Dec 8
Aqua Vista

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 $134
CA $342 total
includes taxes & fees
Nov 30 - Dec 1
The SandPiper

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

16. 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 $491 total
includes taxes & fees
Nov 12 - Nov 13
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

17. 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 $438
CA $500 total
includes taxes & fees
Nov 19 - Nov 20
North Fork Resort

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 $275
CA $605 total
includes taxes & fees
Nov 12 - Nov 13
Beach Block Hideaway

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

20. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (689 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 15 - Nov 16
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shelter Island Heights Hotel Reviews

Find out more about Shelter Island Heights

Shelter Island Heights Chalets information

Number of reviews
2,302
Accommodation
1 Chalets
Lowest Price
CA $261
Highest Price
CA $605

Explore a world of travel with Expedia