Lodging Image

Search Shelter Island hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shelter Island hotels

1. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (61 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is NZ$620
includes taxes & fees
30 July - 31 July
Shelter Island House

2. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (42 reviews)
"location!"
United States
Sharon
The price is NZ$718
includes taxes & fees
23 Aug - 24 Aug
The Chequit

3. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is NZ$616
includes taxes & fees
27 July - 28 July
West Neck Guesthouse

4. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (356 reviews)
"Great place! We really Enjoyed the room and vibe !"
United States
Zoe
The price is NZ$477
includes taxes & fees
29 July - 30 July
Zey Hotel

5. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (94 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is NZ$1,420
includes taxes & fees
16 Aug - 17 Aug
The Pridwin Hotel

6. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (299 reviews)
"It is a beautiful upscale property. The rooms are very comfortable & had all the amenities you needed. Very good location making it accessible for anything you wanted to do in the area."
United States
Sue
The price is NZ$772
includes taxes & fees
28 July - 29 July
The Shoals Suites and Slips

7. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (667 reviews)
"Location was the best. Enjoyed using the pool. View from the room of the Long Island sound was incredible. We had dinner at Haylard restaurant. On the premises and it was delicious."
United States
rosemary
The price is NZ$814
includes taxes & fees
5 Aug - 6 Aug
Sound View Greenport

8. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (34 reviews)
"Great stay & great staff!"
United States
James
The price is NZ$776
includes taxes & fees
29 July - 30 July
North Fork Resort

9. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (629 reviews)
"Very nice property/staff and a great location"
United States
David
The price is NZ$752
includes taxes & fees
29 July - 30 July
The Harbor Front Inn

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (275 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is NZ$883
includes taxes & fees
30 July - 31 July
Cliffside Resort Condominiums

11. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (160 reviews)
"Amazing!"
United States
Joseph
Silver Sands Motel & Beach Bungalows

12. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (185 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is NZ$1,137
includes taxes & fees
29 July - 30 July
The Menhaden

13. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (203 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
United States
kerri
The price is NZ$991
includes taxes & fees
26 July - 27 July
American Beech Hotel

14. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (647 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is NZ$998
includes taxes & fees
18 Aug - 19 Aug
Sag Harbor Inn

15. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (325 reviews)
"It was a nice motor lodge with chairs for sitting outside. There’s also a pool out back that was great."
United States
David
The price is NZ$182
includes taxes & fees
23 Aug - 24 Aug
Clinton Motel

16. 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, (1,003 reviews)
"It was in a good location and less expensive than area hotels."
United States
David
The price is NZ$201
includes taxes & fees
10 Aug - 11 Aug
Pier Blue Inn Old Saybrook - Essex

17. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,006 reviews)
"Clean room , good breakfast"
United States
Fernando
The price is NZ$234
includes taxes & fees
23 Aug - 24 Aug
Quality Inn Old Saybrook - Westbrook

18. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (484 reviews)
"Nice place , served it's purpose. Bed was very comfortable."
United States
Kenneth
The price is NZ$159
includes taxes & fees
29 July - 30 July
Econo Lodge Inn & Suites Old Saybrook Westbrook

19. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (245 reviews)
"Staff was helpful. Place is quiet. Room was a little outdated."
United States
Samantha
The price is NZ$156
includes taxes & fees
30 July - 31 July
Lamplighter Motel - Clinton, Connecticut

20. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.6 out of 10, Excellent, (780 reviews)
"Parking was easy. The grounds and room were clean. It was 5 minutes away from the Jamesport Triathlon."
United States
Diane
The price is NZ$319
includes taxes & fees
28 July - 29 July
Shorewood Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

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

Silver Beach

Silver Beach offers a tranquil coastal retreat on Shelter Island with direct access to the sound. This charming area features weathered cottages and natural shorelines perfect for peaceful waterfront strolls. Shell Beach provides a serene spot for swimming and sunbathing. The neighborhood's calm waters make it ideal for kayaking and small boat activities. Enjoy the scent of salt air mixed with pine and beach roses. Most visitors bring supplies or travel to nearby island markets since Silver Beach maintains its residential character.

Menantic Creek

Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes centre stage. This residential haven features classic Hamptons-style homes with private docks nestled among mature trees. The winding creek waters create a tranquil backdrop for a truly authentic island experience. The area provides excellent opportunities for kayaking, paddleboarding, and birdwatching along pristine shorelines. Visitors can easily explore nearby attractions like Wades Beach and Shelter Island Historical Society. Those seeking quiet relaxation will appreciate the gentle creek sounds and salt-tinged air that define this serene coastal retreat.

Coecles Harbor

Coecles Harbour offers a peaceful retreat where pristine waterfront paths wind along Peconic Bay. Luxury yachts and sailboats dot the protected marina, creating a classic New England coastal scene. Wooden docks extend into calm waters, providing perfect sunset viewing spots. This upscale Shelter Island area balances authentic maritime character with holiday amenities. Visitors can enjoy swimming at Menhadden Lane Beach or explore by kayak and paddleboard. The quiet atmosphere, with only the sounds of lapping waves and seabirds, makes it ideal for those seeking a serene coastal escape.

Hay Beach

Hay Beach offers a tranquil peninsula retreat on Shelter Island, away from the bustling Hamptons scene. This residential haven is surrounded by water on three sides with several beach access points for scenic coastal views. Private waterfront homes and cottages create a peaceful atmosphere where natural beauty takes centre stage. Visitors can explore Menhadden Lane Beach or take short trips to nearby Gardiner's Bay Country Club. The neighborhood's charm lies in its uncrowded shoreline paths and pristine waters. Perfect for kayaking, swimming, and sunset watching, Hay Beach delivers a genuine low-key coastal experience.

Shorewood

Shorewood offers a peaceful retreat on Shelter Island with pristine shorelines and scenic waterfront paths. Classic Hamptons-style cottages with cedar shingles and white trim line the quiet, tree-lined streets. The neighborhood's charm lies in its natural beauty and exclusive residential character. Wades Beach beckons with sandy shores and calm bay waters perfect for swimming and kayaking. Visitors appreciate the minimal tourist crowds and opportunities for stargazing at night. The salt air mingles with pine scents while gentle waves create a soothing natural soundtrack.

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.

A wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

Recent Reviews in Shelter Island

More cheap accommodation in Shelter Island

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Shelter Island boasts beautiful beaches, perfect for relaxation and sunbathing.
  • Outdoor Adventures: Enjoy activities like golfing, kayaking, and exploring scenic parks and nature reserves.
  • Rich History: Visit the Shelter Island Historical Society to learn about the island's unique heritage.
  • Serene Retreats: Unwind at local retreat centres, surrounded by the island's natural beauty.
  • Charming Accommodation: Choose from delightful bed and breakfasts and intimate inns for a memorable stay.

Find great hotels near Shelter Island

Discover a delightful range of accommodation options on Shelter Island, where you can find everything from charming bed and breakfasts to intimate inns and agritourism properties. With a focus on family-friendly experiences and pet-friendly amenities, Shelter Island hotels cater to every traveler's needs, ensuring a memorable stay amidst stunning natural beauty.

  • Sound View Greenport: This 3.5-star hotel offers a charming retreat just 6.4km from Shelter Island. Known for its family-friendly atmosphere, Sound View Greenport features direct access to the beach, making it an ideal choice for those seeking a coastal experience. The property provides amenities for children, including complimentary cribs and safety features like window guards. Guests appreciate the spacious accommodations and the relaxed, welcoming vibe that makes it suitable for both beach holidays and business trips.
  • Sag Harbor Inn: Located 8.0km away from Shelter Island, Sag Harbor Inn is a refined 3.5-star lodging option, earning a stellar guest rating of 9.4 out of 10. It's particularly appealing for business travellers, offering a professional environment without sacrificing comfort. The hotel’s proximity to local dining and shopping enhances its appeal, while the well-appointed rooms provide a serene space to unwind after a day of meetings or exploration.
  • The Harbor Front Inn: Just 4.8km from Shelter Island, The Harbor Front Inn combines a business-friendly atmosphere with a pet-friendly policy, making it a unique option for travellers. This 3.5-star property welcomes dogs and offers various amenities to ensure a comfortable stay for both pets and their owners. Guests enjoy the scenic views and convenient location, which provides easy access to local attractions. The Harbour Front Inn is a great choice for those looking to blend work with leisure while enjoying the company of their furry friends.

Where to stay near Shelter Island

During your visit to Shelter Island, you'll uncover its enchanting charm, perfect for outdoor adventures and romantic beach getaways. Explore the scenic beauty and historical vibes of this idyllic destination, while nearby Long Island offers family-friendly excursions and luxurious experiences. Don’t miss the stunning views at Sunset Beach, where you can unwind and soak in the atmosphere. Whether you’re on a budget or seeking a lavish retreat, Shelter Island has something special for every traveller.

  • Hamptons: Located a mere 14.5km from Shelter Island, the Hamptons are renowned for their stunning beaches and vibrant summer atmosphere. This coastal haven offers a romantic escape with its picturesque scenery and outdoor activities. While the peak season runs from June to August, the Hamptons also provide a quieter charm in the off-peak months. Visitors can indulge in a round of golf, explore scenic ski fields during winter, or simply relax by the beach or lakeside. It’s a perfect spot for those looking to combine leisure with a touch of elegance.
  • Greenport: A charming city only 4.8km away from Shelter Island, Greenport is a delightful destination for outdoor enthusiasts and romantics alike. This quaint seaside town sees its highest number of visitors from June to August, making it a lively spot in summer. Visitors can explore its beautiful parks, enjoy live music concerts, or unwind on its lovely beaches. Greenport's vibrant atmosphere, coupled with its recreational areas, make it an ideal location for leisurely strolls and enjoying the coastal ambience.
  • Sag Harbor: Located just 8.0km from Shelter Island, Sag Harbor is a historic whaling village that has transformed into a chic getaway. With a seasonal influx of visitors peaking during the summer months, Sag Harbor offers a blend of outdoor adventures and romantic settings. Golf enthusiasts will find plenty of options, while the stunning beaches and serene lakes provide perfect spots for relaxation. The charming streets are lined with boutique shops and delightful eateries, making it a must-visit for those seeking a unique coastal experience.

Things to do near Shelter Island

Shopping

For unique gifts and souvenirs, check out the local shops on Shelter Island, such as the Shelter Island Craft Shop for handmade items and the Islander for beach-themed gifts. If you’re up for a drive, visit the nearby Greenport Village for more extensive shopping options and charming boutiques.

Recreation

At Shelter Island's The Spa at the Chequit, indulge in rejuvenating treatments inspired by the coastal environment, alongside holistic wellness experiences. Nearby, explore the serene surroundings at Mashomack Preserve, where nature walks and birdwatching provide a peaceful escape, perfect for relaxation and reflection.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 35.4km from Shelter Island, where the adrenaline of competitive sports fills the air. For more racing excitement, head to Waterford Speedbowl, 38.6km away, offering an energetic atmosphere for motorsport enthusiasts.

Nightlife

Shelter Island offers a relaxed nightlife atmosphere, with venues like The Chequit providing a charming bar scene and live music. The Islander is ideal for a casual evening, featuring vibrant outdoor seating and local brews. Enjoy the waterfront views at Sunset Beach for a laid-back yet lively experience.

*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 near Shelter Island

Shelter Island is ideal for outdoor and romantic beach holidays, offering a range of attractions like beautiful beaches, urban parks, and historic buildings. Visitors can immerse themselves in local culture and nature, with opportunities to explore the Shelter Island Historical Society for a deeper understanding of the area. This charming destination promises a variety of experiences that cater to both relaxation and adventure.

  • East Hampton Main Beach: Located 19.3km from Shelter Island, East Hampton Main Beach offers stunning ocean views and a relaxed atmosphere. Its soft sands and gentle waves create an ideal setting for sunbathing and beach walks, perfect for soaking up the coastal vibes.
  • Norman E. Klipp Marine Park: Just 4.8km away, this marine park is a haven for adventure seekers and families alike. With opportunities for kayaking, fishing, and exploring tidal pools, it provides a unique environment to connect with nature and enjoy recreational activities.
  • Havens Beach: Situated 8.0km from Shelter Island, Havens Beach features picturesque scenery and a tranquil atmosphere. This beach is perfect for a peaceful day by the water, allowing visitors to relax and enjoy the serene surroundings.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Accessing Shelter Island from New Zealand involves flying into major airports like New York's JFK and LaGuardia, or Hartford's Bradley International Airport. JFK is located 130.4km from Shelter Island, with nearby hotels such as The William Vale and Arlo Williamsburg, both 17.7km away. LaGuardia is 133.6km away, offering luxurious options like Hilton Club The Quin and The Plaza, both within 9.7km. Alternatively, Bradley International Airport is 99.8km from Shelter Island, with convenient stays like DoubleTree by Hilton Hartford nearby, just 1.6km away. Each airport provides various transport services for easy access to your accommodation.

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 15.5 mi (24.9 km) from the heart of Shelter Island, Pier Blue Inn Old Saybrook - Essex is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Gurney's Montauk Resort & Seawater Spa and Montauk Yacht Club. 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?
The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Shelter Island is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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. Offers a seasonal outdoor pool, an indoor pool and a private beach. Montauk Yacht Club and Sound View Greenport 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. A top sight in the area is The Hamptons Beaches. In Shelter Island, there are 105 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, Wades Beach and Mashomack Preserve. Additionally, you'll find The Hamptons Beaches in the area. 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.

Explore a world of travel with Expedia