𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Shelter Island from RM362 (2026) - Fully Refundable Options

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Go beyond your typical stay in Shelter Island

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

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

1. The Chequit

The Heights

Patrick

RM731

RM835 total

includes taxes & fees

8 Nov - 9 Nov

2. Shelter Island House

Shelter Island Heights

Dorothy

RM821

RM938 total

includes taxes & fees

28 Oct - 29 Oct

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

A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

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

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

3. House on Chase Creek

The Heights

Tracey

RM755

RM862 total

includes taxes & fees

16 Nov - 17 Nov

A lakeside patio with outdoor seating and a view of the water.

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

A grassy area with trees and a view of a body of water.

4. Silver Sands Motel & Beach Bungalows

Greenport

Keith

RM1,143

RM1,306 total

includes taxes & fees

2 Nov - 3 Nov

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

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.

5. Zey Hotel

Greenport

Renee

RM744

RM850 total

includes taxes & fees

28 Oct - 29 Oct

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 child playing with a colorful kite in a grassy field.

A swimming pool with a wooden deck, lounge chairs, and a fence.

6. The Harbor Front Inn

Greenport

Antrii

RM731

RM951 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

7. Oyster Estate

Greenport

Allison

RM918

RM1,157 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

A storefront with a sign reading "THE SHOALS".

8. The Shoals Suites and Slips

Southold

Masayo

RM757

RM967 total

includes taxes & fees

9 Nov - 10 Nov

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".

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

A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.

9. American Beech Hotel

Greenport

Mary

RM1,024

RM1,333 total

includes taxes & fees

19 Oct - 20 Oct

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

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.

A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

10. The Menhaden

Greenport

Daniel

RM1,410

RM1,775 total

includes taxes & fees

15 Nov - 16 Nov

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

A beach bar with wooden chairs and a small table, overlooking the sea.

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

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

11. Sound View Greenport

Greenport

Irene

RM731

RM952 total

includes taxes & fees

16 Nov - 17 Nov

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

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.

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

12. Sag Harbor Inn

Sag Harbor

Terri

RM894

RM1,021 total

includes taxes & fees

1 Nov - 2 Nov

13. Cliffside Resort Condominiums

Greenport

William

RM690

RM1,241 total

includes taxes & fees

12 Nov - 13 Nov

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

A tented accommodation with a bed, television, and a small table with a chair.

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

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

14. North Fork Resort

Greenport

Harold

RM1,311

RM1,498 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

15. Faraway Sag Harbor

Sag Harbor

Thomas

RM1,506

RM1,893 total

includes taxes & fees

16 Nov - 17 Nov

Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

A wooden building with a white window and a balcony.

A room with a large bay window, a chandelier, and wall sconces.

A beach with pebbles and sand, a sunset, and a calm sea.

16. The Sagaponack

Wainscott

Jane

RM819

RM1,099 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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.

17. Hyatt Place Long Island East End

Riverhead

Timothy

RM519

RM592 total

includes taxes & fees

3 Nov - 4 Nov

A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

18. The Bentley Hotel Southampton

Southampton

RM584

RM667 total

includes taxes & fees

16 Nov - 17 Nov

A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

A living room with a fireplace, two sofas, a coffee table, and a chair.

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

19. Journey East Hampton

East Hampton North

Erika

RM1,010

RM1,270 total

includes taxes & fees

9 Nov - 10 Nov

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

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.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

20. Water's Edge Resort & Spa

Westbrook Center

Laurie

RM728

RM908 total

includes taxes & fees

1 Nov - 2 Nov

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Where to stay in Shelter Island

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

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.

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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 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.

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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 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.

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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 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.

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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 harbour 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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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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Gardiner's Bay Country Club

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

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Shelter Island Historical Society

8.0/10 (1 review)

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

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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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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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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

The Atlantic Hotel

10/10 Excellent

"This is actually a really great place to stay if you want something reasonable in the Hamptons. The rooms are clean and spacious and the grounds of the hotel are beautiful. I highly recommend!!!"

Montauk Blue Hotel

10/10 Excellent

"Lovely stay! Great ocean views from the room and balcony. Staff were very helpful and friendly."

Zey Hotel

10/10 Excellent

"The staff particularly James were over the top accommodating!!"

Beachcomber Resort at Montauk

10/10 Excellent

"Everything was wonderful…location, view, amenities made our stay so memorable. Can’t wait to go back!"

Offshore Montauk

10/10 Excellent

"This was my first time staying @ this property. The staff were so kind & helpful! The gentleman at the front desk was beyond helpful from the moment we checked in, to the moment we left! This team knows the meaning of hospitality! 5 star service Would stay here again !! Thank you :)"

Sound View Greenport

10/10 Excellent

"The breakfast could have had a better choice."

The Bentley Hotel Southampton

10/10 Excellent

"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."

Quality Inn Old Saybrook - Westbrook

8/10 Good

"Only thing I would say is the TV in the room. Every channel was blurry and you couldn’t really see anything."

Ocean Surf Resort

10/10 Excellent

"Perfect for weekend stay"

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

RM314

RM362 total

19 Oct - 20 Oct

includes taxes & fees