Photo by Brian V. Rowe

Find hotels in Shelter Island Heights, NY from ฿2,320

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shelter Island Heights hotels

View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is ฿3,232
฿3,693 total
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Exterior
The Rams Head Inn

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
United States
Lana
The Rams Head Inn
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is ฿3,414
฿3,900 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Long Island East End
Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (880)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is ฿3,139
฿3,610 total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn Old Saybrook - Westbrook
Front of property – evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1273)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is ฿4,301
฿5,522 total
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ฿3,072
฿3,971 total
includes taxes & fees
29 Dec - 30 Dec
Hamlet Inn
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1001)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex
Indoor pool, a heated pool
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
2.5 star property
Niantic
8.4 out of 10, Very good, (1000)
"Clean Room/Polite staff/ Breakfast was basic/ pool area looked maintained."
United States
Sara
The price is ฿2,513
฿2,889 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sleep Inn & Suites Niantic North
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (711)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
Ocean View 2 Queens | Premium bedding, pillow-top beds, blackout curtains, free WiFi
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (87)
"Hotel was beautiful !!"
United States
Erica
The price is ฿3,603
฿5,889 total
includes taxes & fees
11 Jan - 12 Jan 2026
Offshore Montauk
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (552)
"Room and staff were amazing. "
United States
Manuel
The price is ฿4,194
฿5,636 total
includes taxes & fees
26 Jan - 27 Jan 2026
The Harbor Front Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (463)
"We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !"
United States
Robert
The price is ฿2,080
฿2,392 total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (601)
"Great view but a gas station has a better breakfast. "
United States
Michael
The price is ฿4,049
฿5,470 total
includes taxes & fees
29 Dec - 30 Dec
Sound View Greenport
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is ฿2,421
฿2,784 total
includes taxes & fees
29 Dec - 30 Dec
Clinton Motel
Lobby
Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
2.5 star property
Niantic
9.0 out of 10, Wonderful, (453)
"Easy check in and check out, comfortable bed, clean"
United States
Eric
The price is ฿2,867
฿3,297 total
includes taxes & fees
30 Dec - 31 Dec
Best Western Niantic - New London/Mystic Area
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (409)
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is ฿3,883
฿4,468 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (975)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Garden Suite King | Premium bedding, down duvets, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (231)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is ฿5,757
฿6,577 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Shoals Suites and Slips
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (204)
"Good location. Nice people!! "
United States
Theresa
The price is ฿3,259
฿3,886 total
includes taxes & fees
29 Dec - 30 Dec
Southampton Long Island Hotel
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas for the activities you enjoy most.

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Stay near popular Shelter Island Heights attractions

Crescent Beach

4.6/5 (7 reviews)
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
See properties

Menhadden Lane Beach

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
See 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
View of Dering Harbor
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Shelter Island Heights Hotel Reviews

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Hotel was beautiful !!"
Erica 1-night trip
Posted 5 days ago
Offshore Montauk

More cheap stays in Shelter Island Heights

Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

269 Flanders Rd Niantic CT
The price is ฿2,482 per night from 29 Dec to 30 Dec
฿2,482
฿2,855 total
29 Dec - 30 Dec
includes taxes & fees
6.8/10 (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Shelter Island Heights?
House on Chase Creek is ranked highly by Expedia customers. This guest house offers free parking and free WiFi. Shelter Island House is another top choice for your trip based on reviews. See all available top hotels, or vacation rentals in Shelter Island Heights.
If I need to cancel my hotel reservation in Shelter Island Heights, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island Heights.
What's the best family accommodation in Shelter Island Heights?
The Pridwin Hotel is a hotel with a private beach and a restaurant, and it's a top choice on Expedia for families. Shelter Island House is another good choice for your child-friendly holiday. Also, attractions in the area such as Railroad Museum of Long Island and Shelter Island Whale's Tail are fun for children of all ages. Find more child-friendly accommodations in Shelter Island Heights.
What's the best dog-friendly accommodation option in Shelter Island Heights?
The Chequit is a top hotel for people travelling with their pets, and offers a restaurant and a coffee shop/cafe for its human guests. Other good choices to stay with your pet include The Rams Head Inn and SEVEN - Shelter Island Guest House. See more pet-friendly hotel accommodations in Shelter Island Heights.
What's the best place to stay to stay near the beach in Shelter Island Heights?
The Pridwin Hotel is a top beachfront hotel offering a seasonal outdoor pool and free breakfast, located within a short 1-minute walk of Crescent Beach . See more stays near the beach in Shelter Island Heights.
What's the best accommodation for a golf trip to Shelter Island Heights?
House on Chase Creek is a top guest house that has an adjacent golf course and features free WiFi. Other good options to stay near a golf course include Shelter Island House and SEVEN - Shelter Island Guest House. You can tee off at Shelter Island Country Club during your trip. See more golf hotels in Shelter Island Heights.
What are some accommodation options with pools in Shelter Island Heights?
The Pridwin Hotel is a top hotel with a seasonal outdoor pool, a private beach and a full-service spa. View all hotels with pools in Shelter Island Heights.
What is the best spa hotel in Shelter Island Heights?
The Pridwin Hotel is a top spa hotel featuring a private beach, a fitness centre, a bar and a restaurant. Spend an afternoon at Pridwin Spa where you'll find facials, body scrubs, and Swedish massages and more. See all spa hotels in Shelter Island Heights.
How is it to stay in Shelter Island Heights?
Visitors to Shelter Island Heights will definitely enjoy the beaches. Tourists can also enjoy the city's golf courses, entertainment choices and theatres. In Shelter Island Heights, there are 46 hotels and other accommodation options to choose from. Find out more about Shelter Island Heights.
What should I do while I'm visiting Shelter Island Heights?
Natural beauty is on display at Sunset Beach, Crescent Beach and Menhadden Lane Beach. A couple of additional sights to add to your itinerary are Shelter Island Country Club and Sylvester Manor. Take a look at what more there is to see and do in Expedia's Shelter Island Heights guide.
What's the weather like in Shelter Island Heights?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island Heights is 1452 mm.