Top 10 Hotels in Shelter Island, NY from ￥13,186 - Competitive Prices

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Our top choices for Shelter Island hotels

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 large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

1. The Chequit

The Heights

Patrick

￥28,328

￥32,364 total

includes taxes & fees

Nov 1 - Nov 2

A serene landscape with a calm body of water reflecting trees with autumn foliage.

A sign for 'House on Chase Creek' with a duck illustration.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

2. House on Chase Creek

The Heights

Tracey

￥29,239

￥33,405 total

includes taxes & fees

Nov 5 - Nov 6

3. Shelter Island House

Shelter Island Heights

Dorothy

￥31,832

￥36,367 total

includes taxes & fees

Oct 25 - Oct 26

A lakeside patio with outdoor seating 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.

4. Silver Sands Motel & Beach Bungalows

Greenport

Keith

￥37,645

￥43,009 total

includes taxes & fees

Nov 1 - Nov 2

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 kitchen counter with a bottle of wine, a glass, and a basket of snacks.

A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

5. The Harbor Front Inn

Greenport

Antrii

￥23,168

￥30,988 total

includes taxes & fees

Nov 22 - Nov 23

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

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.

A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

6. The Menhaden

Greenport

Daniel

￥52,022

￥65,762 total

includes taxes & fees

Nov 16 - Nov 17

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 restaurant with a signboard listing its hours of operation.

A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

7. Zey Hotel

Greenport

Renee

￥24,502

￥27,992 total

includes taxes & fees

Nov 9 - Nov 10

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A storefront with a sign reading "THE SHOALS".

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

8. The Shoals Suites and Slips

Southold

Masayo

￥29,339

￥37,474 total

includes taxes & fees

Nov 1 - Nov 2

A spacious room with wicker furniture, large windows, and a view of the sea.

A coastal building with large windows, a deck, and a view of the sea at sunset.

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

9. Sound View Greenport

Greenport

Christine

￥25,485

￥33,633 total

includes taxes & fees

Nov 22 - Nov 23

A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

An outdoor dining area with tables and chairs, string lights, and hanging lanterns.

A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

10. American Beech Hotel

Greenport

Mary

￥39,669

￥51,647 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.

A dining area with a round table, chairs, a vase, and a painting on the wall.

A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

11. Oyster Estate

Greenport

Allison

￥34,384

￥43,323 total

includes taxes & fees

Nov 22 - Nov 23

A modern house with a deck, outdoor seating, and a fire pit.

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

A modern living room with a sofa, a dining table, and a kitchen area in the background.

A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

12. North Fork Resort

Greenport

Altynai

￥47,432

￥54,191 total

includes taxes & fees

Oct 25 - Oct 26

A waterfront property with a large house, multiple boats docked, and lush greenery.

A hotel lobby with a sofa, chairs, tables, and a large window.

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

13. Sag Harbor Inn

Sag Harbor

Terri

￥34,639

￥39,575 total

includes taxes & fees

Nov 1 - Nov 2

14. Cliffside Resort Condominiums

Greenport

William

￥26,734

￥48,092 total

includes taxes & fees

Nov 12 - Nov 13

A pool area with umbrellas, potted plants, and a pathway leading to a building.

A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

A spacious living room with a fireplace, comfortable seating, and large windows.

15. Faraway Sag Harbor

Sag Harbor

Thomas

￥51,631

￥64,887 total

includes taxes & fees

Nov 22 - Nov 23

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.

16. Water's Edge Resort & Spa

Westbrook Center

Laurie

￥29,078

￥36,168 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

A bathtub surrounded by candles and flower petals.

A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

17. A Room At The Beach

Bridgehampton

Samantha

￥46,834

￥53,507 total

includes taxes & fees

Oct 25 - Oct 26

A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.

A modern bar area with a long counter, multiple seating options, and a variety of bottles and glasses on shelves.

A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

18. Hyatt Place Long Island East End

Riverhead

Timothy

￥20,878

￥23,854 total

includes taxes & fees

Nov 3 - Nov 4

A modern outdoor deck with lounge chairs and a view of the beach.

A modern hotel with multiple balconies and large windows.

A hotel room with two beds, a flat-screen TV, a ceiling fan, and a large sliding glass door leading to an outdoor area.

A swimming pool with lounge chairs and umbrellas, surrounded by a white building with multiple windows.

19. Offshore Montauk

Montauk

Mary

￥21,679

￥33,805 total

includes taxes & fees

Nov 1 - Nov 2

A spacious hallway with high ceilings, arched columns, and chandeliers.

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.

A modern indoor swimming pool with marble walls and a tiled floor.

20. Montauk Manor

Montauk

Maria

￥23,118

￥29,510 total

includes taxes & fees

Nov 17 - Nov 18

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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

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 neighborhood 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.

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

Coecles Harbor

Coecles Harbor 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 neighborhood 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.

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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 center 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 neighborhood 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.

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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 center 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.

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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.

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Stay near popular Shelter Island attractions

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

Shell Beach

10.0/10 (1 review)

This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbor waters and more dynamic waves, perfect for beachcombing and wildlife spotting.

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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)

Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.

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Shelter Island Historical Society

8.0/10 (1 review)

This historic museum preserves Shelter Island's maritime heritage through artifacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.

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Gardiner's Bay Country Club

This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbor. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.

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Mashomack Preserve

Explore 2,039 acres of pristine wilderness across diverse ecosystems at Mashomack Preserve. The 20+ miles of trails offer intimate encounters with over 200 bird species in tidal creeks, oak forests, and marshes.

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Menhadden Lane Beach

8.8/10 (3 reviews)

This tranquil beach on Shelter Island's east side offers serene views of Gardiner's Bay and the 'Bug' Lighthouse. Bring a blanket, find a quiet spot, and watch sailboats glide across the pristine waters.

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Havens House

Built in 1743, Havens House served as a store, tavern, school, and post office before becoming the Shelter Island Historical Society. Explore its wide plank floors and exhibits showcasing the island's unique heritage.

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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.

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A coastal landscape with a lake, dense greenery, and a sunset sky.

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

10/10 Excellent

"Great"

Ocean Surf Resort

8/10 Good

"Lovely view of the ocean. Bathroom was fine. Room was updated. Only had one nightstand and lamp."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"

Montauk Yacht Club

10/10 Excellent

"Great property and view."

The Bentley Hotel Southampton

10/10 Excellent

"Gorgeous room! Felt like we were home"

Quality Inn Old Saybrook - Westbrook

8/10 Good

"Room was spacious, comfortable and clean. Overall the hotel was nice. The decorating was a bit off putting and looked like it had been done in the 1970’s and never changed; orange and avocado green with brown carpet. If you can get past that it was a good place to stay. Breakfast was very nice with plenty of hot and cold choices. For me, the fact that it was open from 7:30 til 10 am was very nice. I would stay here again."

The Atlantic Hotel

10/10 Excellent

"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"

More cheap stays in Shelter Island