A pebbled beach with a sunset and a distant bridge.

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Our top choices for Shelter Island Heights hotels

An outdoor patio area with string lights, tables, chairs, and a fire pit.
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.
A large, white building with multiple windows and a prominent tree in the foreground.

1. The Chequit

The Chequit
The Heights
United States
Kristin
CA $278
CA $318 total
includes taxes & fees
Oct 5 - Oct 6
The Chequit
A serene landscape with a calm body of water reflecting trees with autumn foliage.
A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
A sign for 'House on Chase Creek' with a duck illustration.

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
CA $304
CA $348 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek

3. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
CA $285
CA $325 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A bedroom with a bed, bedside tables, a lamp, a window, and a door.
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A living room with a beige sofa, a coffee table, and a dining table set with plates and glasses.
A backyard with a large chessboard, outdoor furniture, and a house.

4. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
CA $443
CA $507 total
includes taxes & fees
Oct 1 - Oct 2
West Neck Guesthouse
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A bathroom with a bathtub, green tiled walls, and windows with white blinds.
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.

5. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $239
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Zey Hotel
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.
A grassy area with trees and a view of a body of water.

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sarah
CA $400
CA $457 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A bathroom with a bathtub, a sink, and a shower area.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A room with a bed, a wooden bench, a blue bag, a straw hat, and a towel on the wall.

7. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Jordan
CA $295
CA $377 total
includes taxes & fees
Oct 26 - Oct 27
The Harbor Front Inn
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

8. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $322
CA $408 total
includes taxes & fees
Oct 26 - Oct 27
Sound View Greenport
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 modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

9. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
CA $285
CA $361 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
An outdoor dining area with tables and chairs, string lights, and hanging lanterns.
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.

10. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
CA $324
CA $427 total
includes taxes & fees
Oct 1 - Oct 2
American Beech Hotel

11. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
CA $334
CA $538 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.
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
Lisa
CA $472
CA $595 total
includes taxes & fees
Sep 29 - Sep 30
The Menhaden
A modern house with a deck, outdoor seating, and a fire pit.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
A tented accommodation with a bed, television, and a small table with a chair.
A modern living room with a sofa, a dining table, and a kitchen area in the background.

13. North Fork Resort

North Fork Resort
Greenport
United States
Harold
CA $369
CA $421 total
includes taxes & fees
Oct 27 - Oct 28
North Fork Resort
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 sign for Oyster Estate with a tree in the background.
A wooden reception desk with a notepad, a vase with dried flowers, and various decorative items on shelves above.
A cozy bedroom with a wooden headboard, a bedside table with a lamp, a vase with flowers, and a bed with a floral bedspread.

14. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
CA $447
CA $563 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
A sign for Pier Blue Guesthouse with a logo and name.
A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.
A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

15. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Laura
CA $111
CA $127 total
includes taxes & fees
Sep 29 - Sep 30
Pier Blue Inn Old Saybrook - Essex
A parking lot with a building in the background.
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

16. Clinton Motel

Clinton Motel
Clinton
United States
Selena
CA $110
CA $127 total
includes taxes & fees
Sep 28 - Sep 29
Clinton Motel
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.
A dining area with tables and chairs, a clock on the wall, and a counter with food items.
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

17. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Renee
CA $151
CA $174 total
includes taxes & fees
Oct 4 - Oct 5
Quality Inn Old Saybrook - Westbrook
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 hallway with a fireplace, a large window, and a built-in shelving unit.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

18. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
CA $458
CA $524 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn
A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.
A bedroom with a dark wooden dresser, a flat-screen TV, a microwave, and a door leading to another room.
A sign for Lamplighter Motel with a 'VACANCY' sign next to it.
A hotel room with a bed, a small table, a chair, a painting on the wall, and a window with a curtain.

19. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
CA $98
CA $112 total
includes taxes & fees
Sep 28 - Sep 29
Lamplighter Motel - Clinton, Connecticut
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

20. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
CA $177
CA $237 total
includes taxes & fees
Oct 6 - Oct 7
The Bentley Hotel Southampton
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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

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

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

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

Zey Hotel

Zey Hotel

8/10 Good
"We got off the Orient Point ferry late in evening and were welcomed so warmly by the host! Its like stepping back to a lovely time with the cozy living room on 2 floors and elegant furnishings. The complimentary coffee and lemon water. We loved the cozy feel of the living room that we just picked up muffins from a bakery and ate them with the coffee there. The ONLY reason we gave 4 stars, not 5 is the room had no sound barrier abd we heard next door t.v. on til almost midnight. We loved our stay other than that.0"
alison g 1-night trip
Posted 21 hours ago
Zey Hotel
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"Beautiful view of the ocean, helpful staff. We will be returning."
Carolyn 3-night trip
Posted 1 day ago
Ocean Surf Resort
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"We stayed in the ocean front room. The room and view were beautiful. We had dinner at GIGIs. The food was good. The menu selection Was limited for us because we do not eat fish. The negative with Gurneys is the rooms are not connected to the main building. They do provide a car service to pick you up. I feel this limits you. We would have gone down for a drink but it seemed too involved to get there. This resort is not for seniors ."
salvatore 2-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Staff was very friendly room was clean bed was comfortable"
Richard 1-night trip
Posted 3 days ago
Ocean Vista Resort
Montauk Manor

Montauk Manor

10/10 Excellent
"The grounds are absolutely beautiful and well manicured. The shuttle service that the hotel offers is a wonderful and extremely helpful option! The staff was very kind and lovely especially Fiorella, Patrick, and Esteven!"
Stephanie 2-night trip
Posted 4 days ago
Montauk Manor
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"I really love this hotel! The rooms are beautiful, the service is excellent, and I’ve had a great experience every time I’ve stayed there. I’ve been a few times already and will definitely be coming back next year!"
Veronika 2-night trip
Posted 4 days ago
Montauk Yacht Club

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 $111
CA $127 total
Sep 29 - Sep 30
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Aderi Hotel Niantic

Aderi Hotel Niantic

239 Flanders Road Niantic CT
CA $116
CA $133 total
Oct 27 - Oct 28
includes taxes & fees
6.4/10 (739 reviews)
Aderi Hotel Niantic
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

5 King Arthur Dr Niantic CT
CA $122
CA $140 total
Oct 18 - Oct 19
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
Sleep Inn & Suites Niantic North
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
CA $126
CA $144 total
Sep 29 - Sep 30
includes taxes & fees
6.8/10 (893 reviews)
Budget Host East End
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $126
CA $180 total
Oct 28 - Oct 29
includes taxes & fees
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $177
CA $237 total
Oct 6 - Oct 7
includes taxes & fees
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 $127 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.

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