Find hotels in Shelter Island, NY from $82

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Compare 4,688 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Front of property - evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
$156 nightly
The price is $178
Dec 4 - Dec 5
Total with taxes and fees
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4.0 star property
Montauk
8.2 out of 10, Very Good, (691)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
$287 nightly
The price is $328
Dec 4 - Dec 5
Total with taxes and fees
Gurney's Montauk Resort & Seawater Spa
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 star property
Old Saybrook Center
9.4 out of 10, Exceptional, (1005)
"Every aspect of this hotel was spotless"
United States
Diane
$264 nightly
The price is $303
Nov 30 - Dec 1
Total with taxes and fees
Saybrook Point Resort & Marina
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (67)
"Small room but clean and just what we needed, had a great stay ! Convenient to shops, food and bars "
United States
VINCENT E
$121 nightly
The price is $138
Nov 21 - Nov 22
Total with taxes and fees
Hampton Bays Hotel on Main
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1004)
"The staff is extremely helpful and polite. The location is wonderful with a beautiful ocean view. I can’t say enough nice things about it!"
United States
Terence
$175 nightly
The price is $202
Nov 23 - Nov 24
Total with taxes and fees
Water's Edge Resort & Spa
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
7.2 out of 10, Good, (969)
"Love the area love the room size clean parking was perfect "
United States
Sherwood
$138 nightly
The price is $158
Dec 4 - Dec 5
Total with taxes and fees
The Atlantic Hotel
Property grounds
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, (1000)
"Always a great stay at Pier Blue. Comfy bed and plenty of room."
United States
Patricia
$71 nightly
The price is $82
Dec 11 - Dec 12
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Exterior
Zey Hotel

Zey Hotel

3.5 star property
Greenport
9.2 out of 10, Wonderful, (288)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
$182 nightly
The price is $208
Dec 4 - Dec 5
Total with taxes and fees
Zey Hotel
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
$147 nightly
The price is $168
Dec 21 - Dec 22
Total with taxes and fees
The Harbor Front Inn
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (337)
"Staff and hotel are lovely "
United States
Steven
$245 nightly
The price is $282
Dec 1 - Dec 2
Total with taxes and fees
Madison Beach Hotel
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1008)
"We were treated very well by Welcome desk staff, Kitchen staff, housekeeping. Will stay again"
United States
Kelly j
$101 nightly
The price is $116
Nov 30 - Dec 1
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Property grounds
The Hampton Maid

The Hampton Maid

2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (683)
"Was so lovely would definitely come back again, very cute clean and safe "
United Kingdom
Maria
$212 nightly
The price is $242
Nov 24 - Nov 25
Total with taxes and fees
The Hampton Maid
Ocean View 2 Queens | 1 bedroom, premium bedding, pillowtop beds, blackout drapes
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
9.4 out of 10, Exceptional, (69)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
$131 nightly
The price is $150
Dec 4 - Dec 5
Total with taxes and fees
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers
Marram

Marram

4.0 star property
Montauk
8.8 out of 10, Excellent, (249)
"We loved everything about our stay here: the beds are comfortable, the fire pits with the smores are a nice touch, the beach is very nice, the view as well; and the food is amazing. The staff is very helpful and friendly!"
Canada
Charlotte
$347 nightly
The price is $396
Nov 24 - Nov 25
Total with taxes and fees
Marram
Front of property
The Preston House & Hotel

The Preston House & Hotel

3.5 star property
Riverhead
9.8 out of 10, Exceptional, (368)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
$180 nightly
The price is $206
Dec 18 - Dec 19
Total with taxes and fees
The Preston House & Hotel
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (569)
"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "
United States
Lori
$209 nightly
The price is $239
Nov 23 - Nov 24
Total with taxes and fees
Sag Harbor Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (437)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$131 nightly
The price is $147
Nov 21 - Nov 22
Total with taxes and fees
Hamlet Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (382)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$139 nightly
The price is $159
Nov 21 - Nov 22
Total with taxes and fees
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (593)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$203 nightly
The price is $232
Nov 23 - Nov 24
Total with taxes and fees
Sound View Greenport
Exterior
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (207)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
$185 nightly
The price is $212
Nov 25 - Nov 26
Total with taxes and fees
The Sagaponack
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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Where to stay in Shelter Island

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

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

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 attractions

Colorful pebbles and shells on a beach

Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties
Man watching sailboat on Long Island Sound

Wades Beach

Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
Central Park summer

Top Shelter Island Hotel Reviews

The Sagaponack

The Sagaponack

10/10 Excellent
"Beautiful room, loved the treats at the galley."
Andrew 1-night trip
Posted 1 day ago
The Sagaponack

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
$71 nightly
The price is $82 total per night from Dec 11 to Dec 12
$82 total
Dec 11 - Dec 12
Total with taxes and fees
7.8/10 Good! (1,002 reviews)

Hotels in Shelter Island with star-rating

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Shelter Island features pristine beaches perfect for relaxation and water activities.
  • Outdoor Adventures: Explore hiking, golfing, and wildlife spotting in the island's scenic natural landscapes.
  • Romantic Getaway: Enjoy a tranquil atmosphere ideal for couples looking for a peaceful retreat.
  • Historic Charm: Visit charming neighborhoods and historic buildings that reflect the island's rich culture.
  • Delightful Accommodations: Choose from a variety of cozy stays, including bed and breakfasts and pet-friendly options.

Find great hotels near Shelter Island

Discover a range of delightful accommodations on Shelter Island, New York, perfect for every type of traveler. From charming bed and breakfasts to inviting agritourism properties, you’ll find pet-friendly options and family-friendly experiences that enhance your stay. Whether you’re seeking luxury or a cozy retreat, Shelter Island boasts some of the best hotels to make your vacation unforgettable.

  • Sound View Greenport: Located just 4 miles from Shelter Island, Sound View Greenport is a 3.5-star hotel that caters to families, business travelers, and pet owners alike. This hotel features a business-friendly atmosphere with amenities like conference space and a meeting room, ensuring that your work needs are met while away from home. Families will appreciate the thoughtful features for children, including complimentary cribs and window guards for added safety. Additionally, the property is pet-friendly, allowing dogs and cats with specific policies in place. Enjoy a blend of leisure and practicality during your stay at this charming hotel.
  • Sag Harbor Inn: Situated 5 miles from Shelter Island, Sag Harbor Inn offers a cozy retreat for business travelers seeking a peaceful environment. This 3.5-star hotel is equipped with essential business amenities, including a meeting room, perfect for small conferences or professional gatherings. The inn's tranquil setting provides a serene escape after a busy day, while its proximity to local attractions makes it an ideal base for exploring the beautiful Sag Harbor area. Experience comfort and convenience in this welcoming atmosphere.
  • The Harbor Front Inn: Just 3 miles from Shelter Island, The Harbor Front Inn is a delightful 3.5-star hotel that combines a business-friendly environment with pet-friendly accommodations. Ideal for travelers who wish to bring their furry friends along, the inn permits pets in rooms and allows dogs on the property. With business amenities available, including meeting facilities, guests can seamlessly blend work and leisure. Enjoy stunning views and a relaxing atmosphere while exploring the vibrant surroundings of this charming inn.

Where to stay near Shelter Island

Escape to Shelter Island for a memorable getaway that offers a perfect blend of scenic beauty and historical charm. Enjoy peaceful days on pristine beaches, explore family-friendly neighborhoods, and savor stunning water views. Nearby Long Island provides additional excursions for outdoor enthusiasts. Whether you seek relaxation or adventure, Shelter Island promises a romantic and tranquil retreat, making it an ideal destination for your next vacation.

  • Hamptons: Located 9 miles away from Shelter Island, the Hamptons are renowned for their stunning beaches and vibrant summer scene. This upscale destination sees a surge of visitors from June to August, drawn by its romantic atmosphere, outdoor adventures, and lively social events. Popular activities include golfing on picturesque courses, attending music concerts, and relaxing at luxurious resorts. Local landmarks like family-friendly beaches and serene lakes provide a perfect backdrop for relaxation and recreation, making the Hamptons an ideal spot for both couples and families alike.
  • Greenport: Just 3 miles from Shelter Island, Greenport is a charming seaside village that offers a delightful mix of outdoor and romantic experiences. With peak travel from June to August, visitors flock here to enjoy the beautiful beaches and participate in various outdoor activities. The vibrant local scene includes golf courses, live music events, and inviting resorts. Attractions like family beaches and event conference venues add to Greenport's appeal, making it a perfect destination for those seeking both adventure and relaxation.
  • Sag Harbor: Situated 5 miles from Shelter Island, Sag Harbor is a picturesque town rich in history and culture. It attracts visitors seasonally, especially during the summer months, who come for its beautiful beaches, outdoor pursuits, and romantic settings. Guests can indulge in golfing, skiing, or simply enjoying the scenic parks and family beaches nearby. With its charming waterfront and bustling local shops, Sag Harbor offers a unique blend of relaxation and adventure that makes it a must-visit on your vacation.

Things to do in and around Shelter Island

Shelter Island, New York, is perfect for outdoor and romantic getaways, offering a range of activities like golfing and skiing. Visitors can enjoy memorable stays, vibrant nightlife, and live music while exploring the island's stunning beaches. Outdoor enthusiasts can spot wildlife and indulge in various experiences amidst the natural beauty. Whether you're looking for relaxation or adventure, Shelter Island has something for everyone.

Shopping

The Greenport Farmers' Market, located 3 miles away, offers a vibrant local atmosphere with fresh produce and unique finds. For fashion and accessories, visit The Style Bar and BookHampton, both situated 5 miles away, featuring stylish apparel and a charming selection of books.

Recreation

Enjoy a fun-filled day at Shelter Island Whale's Tail, where you can play mini-golf in a family-friendly atmosphere. For a more tranquil experience, visit Cedar Point County Park to unwind amidst nature and rejuvenate your spirit with serene trails and beautiful waterfront views.

Adventure

Experience the thrills of Splish Splash Water Park, located 23 miles away, featuring exciting water slides and family-friendly attractions. Explore the scenic Walking Dunes Trailhead, 16 miles away, for an adventurous hike amidst stunning landscapes. For adrenaline seekers, Riverhead Raceway, 22 miles away, offers exhilarating motor racing excitement.

Nightlife

Experience the charm of Shelter Island's nightlife by visiting the nearby Greenport Carousel for a whimsical outdoor vibe. For a blend of culture and romance, enjoy a show at Bay Street Theatre or Guild Hall, both offering lively entertainment perfect for families and couples alike.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Shelter Island

To save money on your trip to Shelter Island, consider visiting from January to March when hotel prices are lowest, with Tuesdays offering the best rates. Use Expedia to compare prices and filter for eco-friendly hotels. Combine your hotel, flights, and activities in a package for additional savings, and join the One Key membership for exclusive discounts. Explore free activities on the island, and utilize public transport or biking to keep travel costs down. This way, you can enjoy a budget-friendly vacation while experiencing all that Shelter Island has to offer.

  • The most and least expensive months on average to stay in a hotel: The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool enables you to set your budget, choose your desired location, and more. You can easily arrange the results to display prices from lowest to highest, ensuring you find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Shelter Island

Shelter Island is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Explore beautiful beaches, historic buildings, and urban parks that cater to visitors interested in culture and family experiences. Don't miss iconic spots like Sunset Beach and the opportunity to see whales. A visit to Shelter Island promises a perfect blend of relaxation and adventure, making it a memorable vacation spot.

  • 67 Steps Beach: Located 4 miles from Shelter Island, 67 Steps Beach offers a serene escape with its sandy shores and tranquil ocean vibes, perfect for sunbathing, swimming, or simply enjoying the scenery.
  • Gardiner's Bay Country Club: Situated within Shelter Island, this golf course country club provides a unique golfing experience with beautifully manicured greens, stunning bay views, and a welcoming atmosphere for both novice and seasoned golfers.
  • Orient Point County Park: About 8 miles from Shelter Island, this urban park features family-friendly activities, walking trails, and picnic areas, making it an ideal spot for outdoor enthusiasts and those looking to enjoy a day in nature.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

The nearest major airports for your trip to Shelter Island

To reach Shelter Island, you can fly into several nearby airports. Islip, NY (ISP-MacArthur) is 44 miles away, with convenient hotel options like Hyatt Regency Long Island and Radisson Hotel Hauppauge-Long Island, both accessible from the airport. New Haven, CT (HVN-Tweed - New Haven Regional) is 32 miles distant, featuring hotels such as The Blake Hotel and Graduate by Hilton New Haven, all within 3 miles of the airport. For closer access, East Hampton, NY (HTO) is just 9 miles away, offering luxury at Mill House Inn and Topping Rose House, both situated 3 miles from the airport, ensuring a smooth transition to your Shelter Island getaway.

Frequently asked questions

When is the best time to go to Shelter Island?
The most popular time to visit Shelter Island is during the summer months, particularly in July. At this time, the island comes alive with warm weather, typically reaching around 75°F, making it great for enjoying the beautiful beaches, outdoor activities, and vibrant local events.

During peak season, from June to August, Shelter Island attracts many visitors looking to unwind and explore its charming landscapes. The delightful summer climate is ideal for activities such as sailing, kayaking, and biking along the scenic trails. You'll find that this is also a wonderful time to indulge in local dining experiences, with many restaurants offering fresh seafood and farm-to-table options, often complemented by stunning views of the water.

For those seeking a quieter experience, consider visiting in September. The crowds begin to thin out, yet the weather remains pleasant, allowing you to enjoy the island's natural beauty without the bustling summer vibe. This can be a great time to partake in the local culture, perhaps by attending one of the many art shows or farmers' markets that showcase the talents of the community.
Where can I find the best nightlife in Shelter Island?
Shelter Island, while renowned for its serene beauty and tranquil atmosphere, offers a more subdued nightlife experience compared to bustling urban centers.

In this charming destination, you can find a few lovely spots that provide a relaxed evening ambiance. The Shelter Island Heights area features quaint bars and casual eateries where you can unwind with a glass of wine or a craft cocktail while enjoying the company of friends or loved ones.

For a taste of local flavor, check out the Sunset Beach, which transforms into a lively spot in the evening, offering a beachfront bar experience with stunning sunset views. Here, you can savor fresh seafood and refreshing drinks while listening to live music during the warmer months.

Additionally, the local community often hosts seasonal events and gatherings that allow visitors to experience the island's charm in a more social setting.
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.
How can I save on a Shelter Island hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Shelter Island hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Shelter Island hotel?
Prices for hotels in Shelter Island often vary, but you can find a great deal from $82 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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