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Top hotels and accommodation in Shelter Island

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is NZ$314
includes taxes & fees
3 Dec - 4 Dec
Montauk Manor

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
The price is NZ$646
includes taxes & fees
3 Dec - 4 Dec
Gurney's Montauk Resort & Seawater Spa

Saybrook Point Resort & Marina

3.5 star property
Old Saybrook Center
9.4 out of 10, Exceptional, (1005)
"Beautiful property, we loved our room, friendly staff. "
United States
Natalie
The price is NZ$504
includes taxes & fees
25 Nov - 26 Nov
Saybrook Point Resort & Marina

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (67)
"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
Hampton Bays Hotel on Main

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1004)
"We love the stay everything was perfect"
United States
angelica
The price is NZ$346
includes taxes & fees
20 Nov - 21 Nov
Water's Edge Resort & Spa

The Atlantic Hotel

2.5 star property
Southampton
7.2 out of 10, Good, (968)
"Love the area love the room size clean parking was perfect "
United States
Sherwood
The Atlantic Hotel

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
Pier Blue Inn Old Saybrook - Essex

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
Zey Hotel

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Awesome stay!!! Great Location "
United States
Bryan
The price is NZ$304
includes taxes & fees
20 Nov - 21 Nov
The Harbor Front Inn

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (337)
"Staff and hotel are lovely "
United States
Steven
The price is NZ$498
includes taxes & fees
7 Dec - 8 Dec
Madison Beach Hotel

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1007)
"We were treated very well by Welcome desk staff, Kitchen staff, housekeeping. Will stay again"
United States
Kelly j
The price is NZ$206
includes taxes & fees
30 Nov - 1 Dec
Quality Inn Old Saybrook - Westbrook

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
The Hampton Maid

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
The price is NZ$265
includes taxes & fees
3 Dec - 4 Dec
Offshore Montauk

Marram

4.0 star property
Montauk
8.8 out of 10, Excellent, (249)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
The price is NZ$694
includes taxes & fees
21 Nov - 22 Nov
Marram

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
The price is NZ$353
includes taxes & fees
3 Dec - 4 Dec
The Preston House & Hotel

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
The price is NZ$368
includes taxes & fees
20 Nov - 21 Nov
Sag Harbor 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
The price is NZ$234
includes taxes & fees
20 Nov - 21 Nov
Hamlet Inn

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
The price is NZ$281
includes taxes & fees
3 Dec - 4 Dec
The Bentley Hotel Southampton

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
The price is NZ$359
includes taxes & fees
20 Nov - 21 Nov
Sound View Greenport

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
The price is NZ$400
includes taxes & fees
20 Nov - 21 Nov
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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Our guide on where to stay in Shelter Island

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

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Shelter Island Historical Society and Sunset Beach.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Silver Beach

While Silver Beach may 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 Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Shelter Island Historical Society.

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 attractions

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.

Central Park summer

Top Shelter Island Hotel Reviews

More cheap accommodation in Shelter Island

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Enjoy beautiful beaches like Sunset Beach, perfect for relaxation and sandcastle building.
  • Outdoor Adventures: Engage in a variety of activities, including golfing and whale watching, amidst scenic landscapes.
  • Charming Accommodations: Choose from delightful hotels and unique agritourism properties catering to all types of travellers.
  • Rich Cultural Experience: Explore historic buildings and urban parks, offering insights into local customs and traditions.
  • Family-Friendly Atmosphere: A welcoming environment with activities suitable for all ages, making it ideal for group retreats.

Find great hotels near Shelter Island

For your stay on Shelter Island, you'll discover a variety of accommodation options, including charming hotels and unique agritourism properties. Whether you’re looking for pet-friendly facilities, family-friendly experiences, or adventure-filled getaways, Shelter Island has something to offer every traveller. Explore the best hotels and accommodations that promise a memorable vacation in this picturesque coastal destination.

  • Sound View Greenport: Nestled along the picturesque shoreline, Sound View Greenport is a delightful 3.5-star hotel ideal for families, beachgoers, and business travellers alike. Located 6.4km from Shelter Island, this property boasts direct beach access, allowing guests to soak up the sun and enjoy water activities. The hotel features excellent business amenities, including a Meeting Room and Conference Space, catering to corporate needs. For families, the hotel offers child-friendly services such as complimentary cribs and window guards, ensuring a safe and enjoyable stay for younger guests.
  • Sag Harbor Inn: Situated 8.0km from Shelter Island, Sag Harbor Inn is a charming 3.5-star hotel perfect for business travellers seeking a tranquil getaway. This property provides essential business amenities, including a Meeting Room, making it an excellent choice for those needing a productive environment away from home. With its inviting atmosphere and proximity to local attractions, guests can unwind after a day of meetings and enjoy the serene surroundings of Sag Harbor.
  • The Harbor Front Inn: Located merely 4.8km from Shelter Island, The Harbor Front Inn is a welcoming 3.5-star hotel that caters to both business and pet-friendly travellers. This property allows pets, ensuring that your furry companions can join in on the adventure. The hotel features essential business amenities and a flexible pet policy, including permitted pets in rooms and waived fees for service animals. With its unique blend of comfort and convenience, The Harbor Front Inn is an excellent choice for those travelling with pets while still needing a productive stay.

Where to stay near Shelter Island

Exploring Shelter Island offers a delightful mix of outdoor adventures and romantic getaways. With stunning beaches like Sunset Beach and charming holiday cottages, you’ll find the perfect spot to unwind. The family-friendly atmosphere and scenic surroundings make it an ideal destination for excursions. From beach access to the best local spots, Shelter Island promises a relaxing holiday filled with memorable experiences.

  • Hamptons: Nestled approximately 14.5km from Shelter Island, the Hamptons are a quintessential summer getaway known for their stunning beaches and vibrant social scene. The area attracts visitors primarily from June to August, offering a romantic and outdoor experience. Indulge in activities like golfing at scenic courses, enjoying live music concerts, or unwinding at luxurious resorts. The local highlights include beautiful beaches and picturesque lakes, making it an ideal spot for relaxation and exploration.
  • Greenport: Located around 4.8km from Shelter Island, Greenport is a charming coastal village that captivates tourists with its outdoor adventures and romantic seaside atmosphere. Peak visitation occurs from June to August, allowing for pleasant experiences amidst the picturesque backdrop. Visitors can enjoy golfing, attend lively music concerts, or relax at delightful resorts. Local attractions include stunning beaches, family-friendly areas, and event venues, offering a perfect blend of leisure and entertainment.
  • Sag Harbor: Just 8.0km away from Shelter Island, Sag Harbor is steeped in maritime history and offers a blend of outdoor activities and beachside relaxation. The vibrant summer months from June to August bring in many visitors, drawn to its romantic charm. Explore local golf courses or take advantage of winter sports at nearby ski fields. With beautiful family beaches and lush parks, Sag Harbor is perfect for those looking to immerse themselves in nature while enjoying the area's rich cultural heritage.

Things to do in and around Shelter Island

Discover the charm of Shelter Island, perfect for outdoor adventures, romantic getaways, and beach fun. Enjoy activities like golfing and skiing, while nearby beaches invite you for sandcastle building and relaxation. Ideal for group retreats, this picturesque destination offers numerous recreational opportunities to make your visit memorable.

Shopping

The Greenport Farmers' Market, located 4.8km away, offers a vibrant public market experience. For some fashion finds, visit The Style Bar, just 8.0km from Shelter Island. If you're up for a drive, Love Lane is a charming shopping area 17.7km away, perfect for family vibes.

Recreation

Shelter Island Whale's Tail offers a fun-filled mini-golf experience, perfect for families seeking adventure. Noyac Golf Club, located 9.7km away, provides a scenic golfing retreat for sports enthusiasts. For relaxation, visit Cedar Point County Park, 8.0km from Shelter Island, where you can unwind in nature's tranquility.

Adventure

At Splish Splash Water Park, located 37.0km from Shelter Island, enjoy thrilling water rides and family-friendly entertainment. For a scenic experience, hike the Walking Dunes Trailhead, 25.7km away, where you can immerse yourself in nature. For adrenaline, try racing at Riverhead Raceway, 35.4km from Shelter Island.

Nightlife

In Shelter Island, the Greenport Carousel offers a charming outdoor atmosphere, perfect for a whimsical evening. For a blend of culture and romance, Bay Street Theatre is a delightful choice. If you're after a cinematic experience, the Regal UA East Hampton cinema promises entertainment in a cozy setting.

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

Booking tips and Expedia advantages for Shelter Island

When planning your trip to Shelter Island, consider visiting between January and March for the lowest hotel rates, as prices rise significantly from June to August. Stay on a Tuesday for the best deals, avoiding the pricier Saturday nights. Use Expedia to search for budget accommodations and package deals that combine your hotel, flights, and activities. Don’t miss out on free activities around the island to keep costs down. Always check for special offers and compare rates to ensure you secure the best deal for your stay.

  • 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you’re looking for. To find the most affordable rates and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by combining your Shelter Island hotel booking with your flights and activities through an Expedia package.

Find the best attractions in and around Shelter Island

Shelter Island offers a perfect blend of outdoor adventures, stunning beaches, and romantic getaways. Visitors can explore historic buildings and urban parks, while enjoying a rich cultural experience with family-friendly activities. Don't miss the chance to spot whales and connect with fellow guests as you immerse yourself in the island's charm. With a variety of attractions catering to every type of traveller, Shelter Island promises a memorable holiday for everyone.

  • 67 Steps Beach: Located 6.4km from Shelter Island, 67 Steps Beach offers a tranquil escape with its stunning coastal views and beach vibes. Perfect for sunbathing, swimming, or enjoying a leisurely stroll, this beach is ideal for relaxation and connecting with nature.
  • Gardiner's Bay Country Club: Situated within Shelter Island, Gardiner's Bay Country Club features a beautifully maintained golf course. With picturesque surroundings, it's an excellent spot for golf enthusiasts seeking to unwind and enjoy a round amidst the scenic landscapes.
  • Orient Point County Park: About 12.9km from Shelter Island, Orient Point County Park is a family-friendly urban park. With plenty of outdoor activities, it offers a great environment for picnics, hiking, and exploring nature while enjoying the vibrant city vibes.

Best time to go to Shelter Island

The best time to visit Shelter Island can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Shelter Island falls in August, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Shelter Island falls in January, 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

When planning your visit to Shelter Island, New York, consider flying into one of the nearby airports. Islip, NY (ISP-MacArthur) is 70.8km away; nearby hotels include the 3.5-star Hyatt Regency Long Island and Jake's 58 Casino Hotel, both 6.4km from the airport, as well as the Radisson Hotel Hauppauge-Long Island, located 14.5km away. Alternatively, New Haven, CT (HVN-Tweed) is located 51.5km from Shelter Island, with excellent options like The Blake Hotel and Graduate by Hilton, both 4.8km from the airport. Lastly, East Hampton, NY (HTO) is just 14.5km away, with luxurious stays like the 5-star Mill House Inn, 4.8km from the airport.

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 18.4 mi (29.7 km) from the heart of Shelter Island, Gurney's Montauk Resort & Seawater Spa is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Pier Blue Inn Old Saybrook - Essex and Montauk Blue Hotel. See all available top hotels, or vacation rentals in Shelter Island.
What are some of the best holiday rentals that Shelter Island has to offer?
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available: This holiday home rental outside of Shelter Island 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.
If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.
What's the best dog-friendly accommodation option in Shelter Island?
Sunset Beach Hotel is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.
What's the best hotel to stay near the beach in Shelter Island?
Sunset Beach Hotel is a top beachfront hotel with free WiFi and free parking, and it's located on Sunset Beach . See more stays near the beach in Shelter Island.
What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Montauk Blue Hotel and Quality Inn Old Saybrook - Westbrook are a couple of other choices that offer an on-site pool. View all hotels with pools in Shelter Island.
What's it like to stay in Shelter Island?
Visitors can enjoy all that Shelter Island has to offer, including the parks, beaches and museums. This city also attracts tourists with its scenic landscape. In Shelter Island, there are 95 hotels and other accommodation options to choose from. Find out more about Shelter Island.
What should I see while I'm in Shelter Island?
Natural beauty is on display at Sunset Beach, Mashomack Preserve and Crescent Beach. A couple of additional sights to add to your itinerary are Gardiner's Bay Country Club and Shelter Island Historical Society. Take a look at what more there is to see and do in Expedia's Shelter Island guide.
What's the seasonal weather in Shelter Island?
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 is 1452 mm.

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