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Our top choices for Shelter Island hotels

A spacious room with wicker furniture, large windows, and a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A beach bar with wooden chairs and a small table, overlooking the sea.

1. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $329
CA $416 total
includes taxes & fees
Oct 27 - Oct 28
Sound View Greenport
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A bar area with stools, a shelf with glasses, and decorative plants.
A bathroom with a bathtub, green tiled walls, and windows with white blinds.
A restaurant with a signboard listing its hours of operation.

2. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $239
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Zey Hotel
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
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.

3. 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 modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.
A storefront with a sign reading "THE SHOALS".

4. 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 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 room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.
A grassy area with trees and a view of a body of water.

5. 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 deck with outdoor seating, overlooking a body of water with a sunset view.
A restaurant with green booths, wooden chairs, and round tables.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

6. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Ann
The Pridwin Hotel
A wooden pathway leading to a beach with a view of the ocean.
A modern living room with a sofa, a chair, a coffee table, and a view of the sea.
A house with a stone wall and a garden with various plants and flowers.
A beachfront property with multiple houses, including a large house with a balcony and smaller houses with wooden facades.

7. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
CA $698
CA $957 total
includes taxes & fees
Sep 30 - Oct 1
Gurney's Montauk Resort & Seawater Spa
A modern outdoor lounge area with a long bench and cushioned seating, a central fire feature, and glass walls offering views of the interior.
A modern outdoor seating area with a glass fire feature and a striped sofa.
An indoor swimming pool with clear glass ceilings, sunlit areas with lounge chairs, and a visible lifeguard station.
A couple sitting on a striped sofa with a fire feature in the center.

8. Hilton Mystic

Hilton Mystic
Mystic
United States
Charles
CA $211
CA $242 total
includes taxes & fees
Sep 27 - Sep 28
Hilton Mystic
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A large, white building with multiple windows and a prominent tree in the foreground.
A staircase with wooden balusters and a white wall.
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

9. The Chequit

The Chequit
The Heights
United States
Kristin
CA $278
CA $318 total
includes taxes & fees
Oct 5 - Oct 6
The Chequit

10. 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 kitchen area with a blue island, wooden accents, and a sign that reads "Delight in the day."
A hotel room with a large bed, two bedside tables with lamps, a chair, a desk, and a window with curtains.
An aerial view of a residential area with a large building, a parking lot, and a lake in the background.
A modern reception area with a wooden reception desk, a green artificial grass rug, and a large abstract wall art piece.

11. Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton
Mystic
United States
Mary
CA $161
CA $185 total
includes taxes & fees
Oct 25 - Oct 26
Spark by Hilton Mystic Groton
A modern outdoor deck with lounge chairs and a view of the beach.
A room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.
A swimming pool with lounge chairs and umbrellas, surrounded by a white building with multiple windows.
A modern hotel with multiple balconies and large windows.

12. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
CA $216
CA $328 total
includes taxes & fees
Sep 30 - Oct 1
Offshore Montauk
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.
A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.
A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

13. The Menhaden

The Menhaden
Greenport
United States
Lisa
CA $472
CA $595 total
includes taxes & fees
Sep 29 - Sep 30
The Menhaden

14. 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 spacious hallway with high ceilings, arched columns, and chandeliers.
A garden pathway with a fence, illuminated by string lights, leading to a building.
A wooden bench with a large planter in front.
A large, historic building with multiple stories and a prominent tower, surrounded by lush greenery and a body of water.

15. Montauk Manor

Montauk Manor
Montauk
United States
Maria
CA $182
CA $236 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".
A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

16. 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
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.
A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

17. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
Bill
CA $253
CA $316 total
includes taxes & fees
Oct 4 - Oct 5
Water's Edge Resort & Spa
A waterfront property with a large house, multiple boats docked, and lush greenery.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A hotel lobby with a sofa, chairs, tables, and a large window.

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 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 large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.

19. 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 bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.
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 poolside area with sun loungers, a pool, and a building with a balcony.
A wooden reception desk with a notepad, a vase with dried flowers, and various decorative items on shelves above.

20. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
CA $447
CA $563 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
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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
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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.
A beach with a wooden sign that reads "Please take off your shoes!"

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.
A pebble beach with calm water, a distant bridge, and a forested island.

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 vacation 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.
A calm lake with reflections of clouds, surrounded by trees and a distant structure.

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.
An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

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

A close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
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
A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
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

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.
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Shelter Island Historical Society

8.0/10 (1 review)
You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.
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Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.
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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?
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Shelter Island Whale's Tail

10.0/10 (1 review)
You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.
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Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
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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
A coastal landscape with a lake, dense greenery, and a sunset sky.

Top Shelter Island 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 less than an hour 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 13 hours 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 23 hours 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 2 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 3 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 3 days ago
Montauk Yacht Club
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Closest to beach and town"
john 1-night trip
Posted 5 days ago
Ocean Resort Inn
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 5 days ago
Budget Host East End
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 13 days ago
Faraway Sag Harbor

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
CA $115
CA $133 total
Sep 29 - Sep 30
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
CA $126
CA $144 total
Sep 27 - Sep 28
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 $137
CA $192 total
Oct 25 - Oct 26
includes taxes & fees
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
CA $137
CA $218 total
Oct 19 - Oct 20
includes taxes & fees
8.6/10 Excellent! (325 reviews)
Ocean Surf Resort
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $204
CA $268 total
Oct 4 - Oct 5
includes taxes & fees
The Bentley Hotel Southampton
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
CA $299
CA $342 total
Oct 13 - Oct 14
includes taxes & fees
The Hampton Maid

Hotels in Shelter Island with star rating

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Enjoy picturesque beaches like Sunset Beach and Crescent Beach, perfect for relaxation and scenic views.
  • Outdoor Adventures: Experience activities such as golf, movie nights under the stars, and exploring charming parks.
  • Romantic Getaways: Ideal for couples, offering a blend of luxurious experiences and intimate retreats.
  • Cultural Exploration: Discover historic sites and local events, enriching your visit with unique island vibes.
  • Diverse Accommodations: Choose from charming bed & breakfasts to pet-friendly lodging, catering to all types of travellers.

Find great hotels near Shelter Island

Discover the charm of Shelter Island, New York, with a range of accommodations that cater to every type of traveller. From inviting bed and breakfast options to unique agritourism properties, you'll find the perfect spot for a memorable family vacation. Many hotels are pet-friendly and offer adventure-filled experiences, ensuring that your stay is both comfortable and enjoyable. Explore the diverse lodging options that Shelter Island has to offer for an unforgettable getaway.

  • Sound View Greenport: A 3.5-star hotel with an impressive guest rating of 8.4, Sound View Greenport is a delightful choice for families and pet owners seeking a beach getaway. Located 6.4km from Shelter Island, this property boasts direct beach access, making it perfect for sun-seekers and water enthusiasts. The hotel provides thoughtful amenities for children, including free cribs and window guards for safety. Pet-friendly policies ensure that your furry companions can join you on your vacation, with specific allowances for dogs and cats. With a welcoming atmosphere and family-oriented services, Sound View Greenport is an ideal destination for a memorable seaside retreat.
  • Sag Harbor Inn: Rated at 3.5 stars and with an exceptional guest rating of 9.4, Sag Harbor Inn is situated 8.0km from Shelter Island, making it an excellent base for business travellers. The hotel’s inviting atmosphere and top-notch service cater to professionals seeking comfort and convenience. While the focus is on business travel, the inn's charming surroundings and close proximity to local attractions provide a perfect balance for relaxation after a day of meetings. Guests appreciate the well-maintained facilities and attentive staff, ensuring a pleasant stay for those on the go.
  • The Harbor Front Inn: This 3.5-star inn boasts a commendable guest rating of 8.8 and is located 4.8km from Shelter Island. The Harbor Front Inn is tailored for both pet-friendly travellers and those on business trips. With amenities that allow pets in rooms and a welcoming stance towards service animals, it’s a great choice for those who wish to travel with their furry friends. The inn combines comfort with practicality, making it an ideal retreat for business guests who also want to enjoy the scenic waterfront views. With its attentive staff and quality facilities, The Harbor Front Inn promises a satisfying stay.

Where to stay near Shelter Island

Discover the charm of Shelter Island, where outdoor adventures and romantic beach vacations await. This picturesque destination boasts stunning scenery and rich history, making it perfect for family-friendly excursions or luxurious getaways. Enjoy the unique atmosphere of nearby cities and neighborhoods, offering a blend of budget-friendly options and upscale experiences. Shelter Island's traditions and convenient location make it an ideal base for exploring the best places this beautiful region has to offer.

  • Hamptons: Nestled 14.5km from Shelter Island, the Hamptons are a renowned getaway known for their stunning beaches and vibrant outdoor scene. This region sees a surge in visitors from June to August, drawn by its romantic ambiance and various activities. Golf enthusiasts can enjoy local courses, while winter visitors can embrace the ski fields. With charming family beaches and picturesque lakes, the Hamptons offer a diverse range of experiences, ensuring relaxation and adventure for all types of travellers.
  • Greenport: Located a mere 4.8km from Shelter Island, Greenport is a charming city that captures the essence of coastal living. The visitor influx peaks during the summer months, offering outdoor enthusiasts a plethora of activities. With beautiful parks and family-friendly beaches, it's an ideal spot for picnics or leisurely strolls. Music concerts and recreational areas enhance the cultural experience, making Greenport a delightful blend of romance and relaxation amidst its scenic backdrop.
  • Noyack: Just 8.0km from Shelter Island, Noyack is a picturesque village perfect for those seeking an outdoor escape. Like its neighbours, Noyack enjoys a seasonal influx of visitors, especially during the summer. With access to beautiful beaches and serene lakes, it’s a romantic getaway that also caters to golf lovers and winter sports enthusiasts. The village's laid-back vibe combined with its scenic beauty makes Noyack a must-visit for a tranquil yet engaging holiday experience.

Things to do in Shelter Island

Discover the charm of Shelter Island, New York, perfect for outdoor and romantic beach getaways. Enjoy activities like golfing, windsurfing, and tennis. Take a scenic boat tour or experience the excitement of Splish Splash water park. Don't miss wellness packages to relax and rejuvenate during your visit, and keep an eye out for lively music concerts that add to the island's vibrant atmosphere.

Shopping

In Shelter Island, visit local shops like the Shelter Island Craft Shop for unique handmade gifts and souvenirs. For a broader shopping experience, if you're up for a drive, check out The Shops at East Wind, located 24.1km away, featuring various boutiques and specialty stores.

Recreation

Experience tranquility at the Shelter Island Meditation Retreat, where guided sessions enhance mindfulness amid serene nature. For rejuvenation, visit the Spa at Shelter Island, offering holistic treatments like massages and facials, perfect for unwinding after a day of exploring the island's beautiful beaches and lush trails.

Adventure

Explore the picturesque landscapes of Shelter Island by kayaking through its serene waters or hiking the trails of Mashomack Preserve, where you can encounter diverse wildlife. For a thrilling experience, try stand-up paddleboarding, offering a unique view of the island’s natural beauty.

Nightlife

The nightlife on Shelter Island offers a relaxed yet vibrant atmosphere. Enjoy cocktails at the charming Sunset Beach Hotel, or unwind at the rustic Islander, where live music often creates a lively backdrop for an enjoyable evening out. Each venue embodies the island's unique coastal charm.

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

Booking tips and Expedia advantages for Shelter Island

  • 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: Utilize Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of hotel you envision. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some money by combining your Shelter Island hotel reservation with your flights and activities by booking a package through Expedia.

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

Frequently asked questions

What is the best area to stay in Shelter Island?
The best area to stay on Shelter Island is the main village of Shelter Island Heights for its convenience and access to amenities.Shelter Island Heights is the island's commercial centre, offering a mix of shops, restaurants, and hotels. It's well-connected by ferry to Greenport on the North Fork, making it an ideal base for exploring both sides of the Peconic Bay. The area is very walkable, with most establishments clustered around the main streets leading from the ferry terminal.For couples seeking a refined and relaxed getaway, Shelter Island Heights offers elegant boutique hotels and fine dining options. You'll find art galleries and charming local shops, great for leisurely strolls. The easy access to the ferry also makes day trips to Greenport's vineyards and breweries very straightforward.Families will also appreciate Shelter Island Heights for its practical location. There are ice cream parlours and family-friendly eateries within easy reach.
What are the best family hotels in Shelter Island?
For families visiting Shelter Island, the Sunset Beach Hotelis an excellent choice.This highly-rated hotel, with a 9.2 review score, is particularly well-suited for families. It offers a range of family-friendly amenities including complimentary cots, beach toys, and games for children. There is also onsite babysitting and childcare services available, providing convenience for parents. The hotel is incredibly well-located, being just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, making it easy to enjoy the local surroundings. Find more child-friendly accommodations in Shelter Island
What are the best spa hotels in Shelter Island?
For a top-rated spa hotel in Shelter Island, the Sunset Beach Hotelis an excellent choice.This hotel, with a superb 9.2 rating, offers a wonderful range of amenities to enhance your spa experience. Guests can enjoy massages on the beach, as well as general massage services, and the rooms feature designer toiletries, Frette Italian sheets, luxurious bathrobes, and comfortable premium bedding. The hotel also provides champagne service and air conditioning for added comfort. It is conveniently located just 0.5 km from Crescent Beach and 0.7 km from Shelter Island Country Club. See all spa hotels in Shelter Island
What are the top pet-friendly hotels in Shelter Island?
For a top pet-friendly hotel in Shelter Island, the Sunset Beach Hotelis an outstanding choice.The Sunset Beach Hotel, with an excellent rating of 9.2, is highly recommended for travellers with pets. It not only permits pets but also provides thoughtful amenities such as food and water bowls, ensuring your furry companions are well catered for. The hotel is wonderfully located, just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, offering easy access for walks and seaside enjoyment. Guests can also indulge in massages on the beach, adding to a relaxing stay for both you and your pet. See more pet-friendly hotels in Shelter Island
What are the best budget hotels in Shelter Island?
For a budget-friendly hotel in Shelter Island, the Sunset Beach Hotelis an excellent choice.This hotel, with a superb 9.2 rating, offers complimentary WiFi and free self-parking, which adds to its value. Guests can also enjoy massages directly on the beach, providing a relaxing experience. Its location is a key highlight, being just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, making it very convenient for beach lovers. View all budget hotels in Shelter Island
What are the best hotels in Shelter Island near Crescent Beach?
For a wonderful stay near Crescent Beach in Shelter Island, the Sunset Beach Hotelis an excellent choice.This highly-rated hotel, with a superb 9.2 review score, is conveniently located just 0.5 km from Crescent Beach. It is also only 0.1 km from Sunset Beach. Guests with families will like the range of amenities, including free cribs, beach toys, and other toys and games specifically for children. On-site babysitting and childcare services are also available, providing added convenience for parents.
When is the best time to go to Shelter Island?
The best time to visit Shelter Island is during the summer months, from June to August, when the weather is warm and all the island's amenities are in full swing.For those seeking a classic summer holiday experience, July and August offer the warmest temperatures, superb for enjoying the beaches and water activities. You'll find all the restaurants and shops open, and there's a lively, yet relaxed, atmosphere across the island. This period is ideal for families and couples looking for a traditional seaside escape with plenty of sunshine.If you prefer a slightly quieter visit with pleasant weather and fewer crowds, late May and early June, or early September, are also excellent choices. The weather is still lovely, most establishments are open, and you can experience the island's natural beauty with a bit more tranquility.
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 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 CA $109 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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