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20 Oct - 21 Oct
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21 Oct - 22 Oct
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24 Oct - 26 Oct
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31 Oct - 2 Nov

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Top hotels and accommodation in Shelter Island Heights

Seasonal outdoor pool, pool umbrellas, pool loungers
The Pridwin Hotel
The Pridwin Hotel
4.0 star property
9.6 out of 10, Exceptional, (82)
"Clean room excellent staff"
United States
Concetta
The Pridwin Hotel
Exterior
The Chequit
The Chequit
3.0 star property
9.0 out of 10, Wonderful, (37)
"A cozy room with great pillows and quiet. Perfect little place. "
United States
Neal
The price is AU$728
includes taxes & fees
23 Oct - 24 Oct
The Chequit
View from property
House on Chase Creek
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (77)
" 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 AU$325
includes taxes & fees
3 Nov - 4 Nov
House on Chase Creek
Front of property – evening/night
Montauk Manor
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1256)
"Beautiful grounds, excellent staff"
United States
Jess
The price is AU$281
includes taxes & fees
3 Nov - 4 Nov
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (671)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "
United States
Amandip
The price is AU$572
includes taxes & fees
4 Nov - 5 Nov
Gurney's Montauk Resort & Seawater Spa
Exterior
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 star property
9.4 out of 10, Exceptional, (1012)
"Beautiful property, we loved our room, friendly staff. "
United States
Natalie
The price is AU$463
includes taxes & fees
6 Nov - 7 Nov
Saybrook Point Resort & Marina
Property grounds
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.8 out of 10, Good, (1017)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"
United States
Laura
The price is AU$137
includes taxes & fees
26 Oct - 27 Oct
Pier Blue Inn Old Saybrook - Essex
Deluxe Double Room, 1 King Bed, City View
Hampton Bays Hotel on Main
Hampton Bays Hotel on Main
2.0 star property
7.0 out of 10, Good, (65)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
The price is AU$236
includes taxes & fees
2 Nov - 3 Nov
Hampton Bays Hotel on Main
Seasonal outdoor pool, pool umbrellas, pool loungers
Marram
Marram
4.0 star property
8.8 out of 10, Excellent, (238)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
The price is AU$490
includes taxes & fees
16 Nov - 17 Nov
Marram
View from property
Ocean Surf Resort
Ocean Surf Resort
2.0 star property
8.4 out of 10, Very good, (220)
"Everything was great "
United States
Darryl
The price is AU$189
includes taxes & fees
22 Oct - 23 Oct
Ocean Surf Resort
Lobby
Best Western Niantic - New London/Mystic Area
Best Western Niantic - New London/Mystic Area
2.5 star property
9.0 out of 10, Wonderful, (402)
"Really enjoyed staying here. Relaxing and pet friendly."
United States
Patrick
The price is AU$164
includes taxes & fees
2 Nov - 3 Nov
Best Western Niantic - New London/Mystic Area
View from room
Offshore Montauk
Offshore Montauk
2.0 star property
9.4 out of 10, Exceptional, (61)
"Great place "
United States
Kevin
The price is AU$438
includes taxes & fees
2 Nov - 3 Nov
Offshore Montauk
Indoor pool, a heated pool
Sleep Inn & Suites Niantic
Sleep Inn & Suites Niantic
2.5 star property
8.4 out of 10, Very good, (1010)
"Small breakfast area lacked enough seating but otherwise a great stop near the casino. "
United States
Theodore
The price is AU$138
includes taxes & fees
9 Nov - 10 Nov
Sleep Inn & Suites Niantic
Exterior
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 star property
8.8 out of 10, Excellent, (1008)
"We love the stay everything was perfect"
United States
angelica
The price is AU$378
includes taxes & fees
26 Oct - 27 Oct
Water's Edge Resort & Spa
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn
The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (524)
"Great location ,beautiful hotel,nice staff"
United States
ROBERT
The price is AU$366
includes taxes & fees
2 Nov - 3 Nov
The Harbor Front Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (1012)
"We have stayed there before so have been pleased with it."
United States
Nancy and Raymond
The price is AU$165
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Old Saybrook - Westbrook
Front of property
The Preston House & Hotel
The Preston House & Hotel
3.5 star property
9.8 out of 10, Exceptional, (366)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is AU$359
includes taxes & fees
2 Nov - 3 Nov
The Preston House & Hotel
Exterior
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (324)
"the staff was exceptional and our dinner was very good"
United States
john
The price is AU$434
includes taxes & fees
30 Oct - 31 Oct
Madison Beach Hotel
King Ocean Front | Balcony view
Montauk Blue Hotel
Montauk Blue Hotel
2.0 star property
9.2 out of 10, Wonderful, (162)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
United States
Jason
The price is AU$205
includes taxes & fees
9 Nov - 10 Nov
Montauk Blue Hotel
Lobby
Aderi Hotel Niantic
Aderi Hotel Niantic
2.0 star property
6.2 out of 10, (687)
"Front desk staff at check in was so polite and friendly!"
United States
Lindsey
The price is AU$104
includes taxes & fees
20 Nov - 21 Nov
Aderi Hotel Niantic
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.
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Our guide on where to stay in Shelter Island Heights

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

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

Shelter Island Country Club

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
Photo by Erisa Dilo
Open Photo by Erisa Dilo

Top Shelter Island Heights Hotel Reviews

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Beautifully renovated , super clean property. High quality sheets, towels, very comfortable bed. We enjoyed easy access to the beach and short distance to many dining options. Had wonderful stay and can't wait to come back."
Andrzej 2-night trip
Posted 3 days ago
Offshore Montauk

More cheap accommodation in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT
The price is AU$137 per night from 26 Oct to 27 Oct
AU$137
26 Oct - 27 Oct
includes taxes & fees
7.8/10 Good! (1,017 reviews)

Frequently asked questions

Where is the best place to stay in Shelter Island Heights?
The Pridwin Hotel is ranked highly by Expedia customers. This hotel offers a full-service spa and a private beach. Other top choices based on reviews include The Chequit and House on Chase Creek. See all available top hotels, or vacation rentals in Shelter Island Heights.
What are some of the best holiday rentals that Shelter Island Heights has to offer?
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available: This holiday home rental outside of Shelter Island Heights is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. See all 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 Sag Harbor Whaling and Historical Museum 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?
Shelter Island House is a top hotel that has an adjacent golf course and features free breakfast. Other good options to stay near a golf course include House on Chase Creek 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. A couple of other options that feature an on-site pool include White Oak Cottage | The Pridwin Hotel and Cottages and Larch Cottage | The Pridwin Hotel and Cottages. 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 54 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.

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