A pebbled beach with a sunset and a distant bridge.

Find hotels in Shelter Island Heights, NY from CA $115

  • 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
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Filter by

Star rating

Guest rating

Our top choices for Shelter Island Heights hotels

An outdoor patio area with string lights, tables, chairs, and a fire pit.
A large, white building with multiple windows and a prominent tree in the foreground.
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.
A staircase with wooden balusters and a white wall.

1. The Chequit

The Chequit
The Heights
United States
Patrick
CA $210
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
The Chequit
A serene landscape with a calm body of water reflecting trees with autumn foliage.
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.
A sign for 'House on Chase Creek' with a duck illustration.

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
CA $261
CA $299 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek
Front of property - evening/night
Terrace/patio
Property amenity
Property amenity

3. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
CA $285
CA $325 total
includes taxes & fees
Oct 19 - Oct 20
Shelter Island House
A lakeside patio with outdoor seating and a view of the water.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.
Outdoor spa tub
A grassy area with trees and a view of a body of water.

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
CA $325
CA $371 total
includes taxes & fees
Nov 2 - Nov 3
Silver Sands Motel & Beach Bungalows
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A child playing with a colorful kite in a grassy field.
A swimming pool with a wooden deck, lounge chairs, and a fence.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Antrii
CA $253
CA $330 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A restaurant with a signboard listing its hours of operation.
A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.
A bathroom with a bathtub, green tiled walls, and windows with white blinds.

6. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $237
CA $271 total
includes taxes & fees
Oct 27 - Oct 28
Zey Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A beach bar with wooden chairs and a small table, overlooking the sea.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

7. Sound View Greenport

Sound View Greenport
Greenport
United States
Christine
CA $253
CA $330 total
includes taxes & fees
Nov 16 - Nov 17
Sound View Greenport
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A dining area with a round table, chairs, a vase, and a painting on the wall.

8. Oyster Estate

Oyster Estate
Greenport
United States
Allison
CA $296
CA $373 total
includes taxes & fees
Nov 18 - Nov 19
Oyster Estate
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
A storefront with a sign reading "THE SHOALS".
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.
A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

9. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Masayo
CA $262
CA $335 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
Terrace/patio
Room
Living area
Room

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
William
CA $239
CA $430 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".
A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.
A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.

11. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
CA $355
CA $462 total
includes taxes & fees
Oct 19 - Oct 20
American Beech Hotel
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.
A modern living room with a grey sofa, black and white patterned rug, and a coffee table.
A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

12. The Menhaden

The Menhaden
Greenport
United States
Daniel
CA $489
CA $615 total
includes taxes & fees
Nov 16 - Nov 17
The Menhaden
A modern house with a deck, outdoor seating, and a fire pit.
A modern living room with a sofa, a dining table, and a kitchen area in the background.
A tented accommodation with a bed, television, and a small table with a chair.
A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

13. North Fork Resort

North Fork Resort
Greenport
United States
Harold
CA $414
CA $473 total
includes taxes & fees
Oct 20 - Oct 21
North Fork Resort
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

14. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
CA $310
CA $354 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

15. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Doug
CA $191
CA $218 total
includes taxes & fees
Oct 31 - Nov 1
The Bentley Hotel Southampton
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

16. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Thomas
CA $464
CA $584 total
includes taxes & fees
Nov 18 - Nov 19
Faraway Sag Harbor
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.
A bedroom with a bed, a door, and a framed picture on the wall.
A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

17. Shorewood Inn

Shorewood Inn
Riverhead
United States
Kathleen
CA $145
CA $166 total
includes taxes & fees
Oct 19 - Oct 20
Shorewood Inn
A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.
A modern bar area with a long counter, multiple seating options, and a variety of bottles and glasses on shelves.

18. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
United States
Timothy
CA $180
CA $205 total
includes taxes & fees
Nov 3 - Nov 4
Hyatt Place Long Island East End
A modern outdoor deck with lounge chairs and a view of the beach.
A modern hotel with multiple balconies and large windows.
A room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.
A hotel room with two beds, a flat-screen TV, a ceiling fan, and a large sliding glass door leading to an outdoor area.

19. Offshore Montauk

Offshore Montauk
Montauk
United States
Mary
CA $178
CA $285 total
includes taxes & fees
Nov 2 - Nov 3
Offshore Montauk
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A dining area with tables and chairs, a clock on the wall, and a counter with food items.
A living room with two sofas, a coffee table, a lamp, and a painting on the wall.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

20. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Amy
CA $137
CA $158 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Old Saybrook - Westbrook
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas and neighborhoods for the activities you enjoy most.
A calm lake reflecting trees and a clear sky.
Photo by Erisa Dilo

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.
A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
See properties

Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
See properties

Sylvester Manor

8.8/10 (3 reviews)
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
See properties

Shelter Island Country Club

10.0/10 (3 reviews)
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
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
A pebbled beach with a sunset and a distant bridge.

Top Shelter Island Heights Hotel Reviews

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Beautiful place to stay . Room has a full kitchen. Also included in the room glasses silverware and dishes . Easy access to the beach. Most enjoyable time ."
John 2-night trip
Posted 19 hours ago
Ocean Vista Resort
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Very clean bathroom. Very dated and weathered furniture. The linens were good. The paint on the door needed cleaned. The receptionist was very personable. We were on the first level and could hear the folks above."
kimberly 1-night trip
Posted 20 hours ago
Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The ambience is amazing! We loved our stay!!"
Christine 1-night trip
Posted 23 hours ago
Sound View Greenport
Zey Hotel

Zey Hotel

10/10 Excellent
"Hotel is in a great location, central to everything. Staff was helpful and courteous. We will definitely be back!"
Joanne 1-night trip
Posted 2 days ago
Zey Hotel
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Great place in Montauk. Beautiful view and room was spacious."
fred 4-night trip
Posted 2 days ago
Beachcomber Resort at Montauk
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Lots of parking, rooms were clean and smelt nice"
miranda 1-night trip
Posted 2 days ago
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."
Cynthia 7-night trip
Posted 5 days ago
The Bentley Hotel Southampton

More cheap stays in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
CA $100
CA $115 total
Oct 19 - Oct 20
includes taxes & fees
8/10 Very good! (1,005 reviews)
Pier Blue Inn Old Saybrook - Essex
Aderi Hotel Niantic

Aderi Hotel Niantic

239 Flanders Road Niantic CT
CA $106
CA $122 total
Nov 18 - Nov 19
includes taxes & fees
6.4/10 (745 reviews)
Aderi Hotel Niantic
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
CA $109
CA $125 total
Oct 27 - Oct 28
includes taxes & fees
Budget Host East End
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

5 King Arthur Dr Niantic CT
CA $132
CA $152 total
Nov 15 - Nov 16
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
Sleep Inn & Suites Niantic North
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $151
CA $208 total
Oct 28 - Oct 29
includes taxes & fees
7.2/10 Good! (1,003 reviews)
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $191
CA $218 total
Oct 31 - Nov 1
includes taxes & fees
9.6/10 Exceptional! (600 reviews)
The Bentley Hotel Southampton

Hotels in Shelter Island Heights with star rating

Frequently asked questions

What is the best area to stay in Shelter Island Heights?
The best area to stay in Shelter Island Heights is the village area itself, particularly around the historic Shelter Island Heights Historic District.This district is the heart of the community, characterised by its historic Victorian homes and tree-lined streets. It's where you'll find most of the island's amenities, including shops, restaurants, and the ferry terminal for easy access to Greenport. The area is very walkable, making it convenient to explore on foot.For couples seeking a relaxing getaway, staying within the historic district offers a quintessential island experience. You'll be close to dining options and can enjoy strolls along the streets admiring the architecture, or head down to Crescent Beach for a peaceful afternoon by the water. Many accommodations here offer a more intimate setting great for two.Families often find the historic district appealing due to its proximity to activities. The village green provides open space for children, and the calm waters of Crescent Beach are suitable for swimming and building sandcastles.
What are the best hotels in Shelter Island Heights that travellers recommend?
One of the best hotels in Shelter Island Heights that travellers recommend is The Pridwin Hotel.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, offers a wonderful experience with its private beach access and a refreshing poolside bar. Guests frequently highlight the beautiful and clean rooms, the amazing amenities, and the great facilities. Many rooms boast breathtaking water and ocean views, and premium bedding and bathrobes add to the comfort. The hotel is conveniently located just 0.4 km from Crescent Beach and 0.9 km from Sunset Beach, making it ideal for beach enthusiasts.
What are the best family hotels in Shelter Island Heights?
For families visiting Shelter Island Heights, The Pridwin Hotel and The Rams Head Inn are both excellent choices.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, is a fantastic option for families. Guests frequently highlight the beautiful and clean rooms, amazing amenities, and great facilities. Families will appreciate amenities such as sofa beds, kids' meals, and a pool with a gate for added safety. Many rooms offer water or ocean views, adding to the relaxing experience. The hotel is also conveniently located near Sunset Beach, just 0.9 km away, and Crescent Beach, a mere 0.4 km away.Another good option is the 4-star Rams Head Inn, rated 7.6. This hotel caters well to families, offering books and games for children, as well as highchairs. Guests can also enjoy a complimentary continental breakfast. It is located 2.5 km from Menhadden Lane Beach. Find more child-friendly accommodations in Shelter Island Heights
What are the best spa hotels in Shelter Island Heights?
For a top-tier spa experience in Shelter Island Heights, The Pridwin Hotel is an excellent choice.This 4-star hotel, boasting an impressive 9.6 rating, offers a full-service onsite spa that provides a wide range of treatments, including Swedish massage, deep tissue massage, body wraps, body scrubs, and hydrotherapy treatments. Guests can also enjoy facial treatments, manicures, pedicures, and a steam room. The Pridwin Hotel is conveniently located just 0.4 km from Crescent Beach and 1.6 km from Shelter Island Country Club, making it ideal for those who appreciate beautiful surroundings and nearby recreational activities. Guests frequently praise its beautiful and clean rooms, amazing amenities, great facilities, and delicious food. See all spa hotels in Shelter Island Heights
What hotels in Shelter Island Heights offer free breakfast?
For hotels in Shelter Island Heights that offer complimentary breakfast, consider The Pridwin Hotel and The Rams Head Inn.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, offers both free breakfast and continental breakfast. Guests frequently mention the beautiful, clean rooms, amazing amenities, and delicious food. This hotel also provides a free ferry terminal shuttle, free self-parking, and free WiFi. It boasts lovely water and ocean views and is conveniently located near Sunset Beach, just 0.9 km away, and Crescent Beach, 0.4 km away.Another option is the 4-star Rams Head Inn, rated 7.6, which also provides free breakfast and continental breakfast. This hotel offers free WiFi, free self-parking, and is situated approximately 2.5 km from Menhadden Lane Beach. Find more hotels with free breakfast in Shelter Island Heights
What are the top pet-friendly hotels in Shelter Island Heights?
For top pet-friendly accommodation in Shelter Island Heights, consider The Rams Head Inn.The 4-star Rams Head Inn, with a rating of 7.6, warmly welcomes pets, specifically dogs. This charming inn offers a delightful dining experience for couples and is conveniently located just 2.5 kilometres from Menhadden Lane Beach. See more pet-friendly hotels in Shelter Island Heights
What are the most romantic hotels in Shelter Island Heights for couples?
For a romantic getaway in Shelter Island Heights, couples should consider The Pridwin Hotel or The Rams Head Inn.The 4-star Pridwin Hotel, with an impressive 9.6 rating, is a beautiful option. Guests frequently praise its amazing amenities, great facilities, and delicious food. Many rooms offer lovely water or ocean views, and the hotel provides complimentary breakfast, including a continental option, and free toiletries. It is conveniently located just 0.4 km from Crescent Beach and 1.6 km from Shelter Island Country Club, making it easy to explore the surroundings.Another option is the 4-star Rams Head Inn, rated 7.6, which features couples' dining. This hotel offers complimentary continental breakfast and free toiletries, along with free self-parking. It is located 2.5 km from Menhadden Lane Beach, providing a quiet setting for a romantic escape. See all romantic hotels in Shelter Island Heights
What are the best hotels in Shelter Island Heights near Crescent Beach?
For hotels in Shelter Island Heights near Crescent Beach, The Pridwin Hotel is an excellent choice.The 4-star Pridwin Hotel, with an impressive rating of 9.6, is located just 0.4 km from Crescent Beach. Guests consistently praise its beautiful and clean rooms, amazing amenities, and great facilities. The hotel also boasts delightful food, and its location is frequently highlighted as a major positive. Many rooms offer water or ocean views, and there is a pool available.
When is the best time to go to Shelter Island Heights?
The best time to go to Shelter Island Heights is during the summer months, from June to September, when the weather is warm and the island is fully operational.During this period, all the island's amenities, including restaurants, shops, and recreational activities, are open and readily available. The ferry service also runs more frequently, making travel to and from the island very convenient. This time of year is superb for those looking to enjoy the beaches and outdoor activities.For those who prefer a quieter experience with pleasant weather, late spring (May) and early autumn (October) are also excellent choices. The crowds are smaller, but the weather is still generally mild enough to enjoy walking, cycling, and the island's natural beauty.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shelter Island Heights.
How much is the nightly rate at a Shelter Island Heights hotel?
Prices for hotels in Shelter Island Heights often vary, but you can find a great deal from CA $115 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia