Shelter Island Holiday Rentals, New York: Private House Rentals

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Go beyond your typical stay in Shelter Island

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Our top choices for Shelter Island hotels

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

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

1. House on Chase Creek

The Heights

Calvin

5.579.627 ₫

6.374.791 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

A dining area with a round table, two chairs, a framed artwork, a vase with flowers, a bottle, and books.

A residential area with a large building, a swimming pool, and a dock extending into a body of water.

A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

2. The Harbor Front Inn

Greenport

Michael

6.741.792 ₫

8.442.921 ₫ total

includes taxes & fees

4 Oct - 5 Oct

3. Shelter Island House

Shelter Island Heights

Dorothy

5.216.400 ₫

5.959.526 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

A backyard with a large chessboard, outdoor furniture, and a house.

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

A beach with a wooden walkway along the shore, calm water, and a sunset sky.

4. West Neck Guesthouse

Shelter Island Heights

Allie

8.125.920 ₫

9.284.026 ₫ total

includes taxes & fees

15 Sept - 16 Sept

A poolside area with lounge chairs and yellow umbrellas.

A cozy interior with a wooden bench, a sofa, and a bar area.

A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

5. Oyster Estate

Greenport

Jenny

8.915.792 ₫

11.233.379 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A seaside dining area with tables, chairs, and umbrellas, overlooking a body of 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.

6. Silver Sands Motel & Beach Bungalows

Greenport

Sirikhwan

8.424.000 ₫

9.624.614 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A deck with outdoor seating, overlooking a body of water with a sunset view.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

7. The Pridwin Hotel

Shelter Island Heights

Anna

13.139.329 ₫

16.512.853 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

8. Sag Harbor Inn

Sag Harbor

Loretta

8.397.432 ₫

9.594.067 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

9. American Beech Hotel

Greenport

Mary

8.055.314 ₫

10.239.942 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A storefront with a sign reading "THE SHOALS".

10. The Shoals Suites and Slips

Southold

Melissa

5.230.901 ₫

6.624.255 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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 modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

11. The Menhaden

Greenport

Lisa

9.557.222 ₫

11.955.859 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

A restaurant with a signboard listing its hours of operation.

A bar area with stools, a shelf with glasses, and decorative plants.

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

12. Zey Hotel

Greenport

Renee

4.373.662 ₫

4.996.908 ₫ total

includes taxes & fees

15 Sept - 16 Sept

An outdoor patio area with string lights, tables, chairs, and a fire pit.

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.

A staircase with wooden balusters and a white wall.

13. The Chequit

The Heights

Kristin

5.365.026 ₫

6.129.542 ₫ total

includes taxes & fees

4 Oct - 5 Oct

14. Cliffside Resort Condominiums

Greenport

Christine

7.488.806 ₫

10.866.700 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

15. Sound View Greenport

Greenport

Irene

6.885.648 ₫

8.607.127 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

16. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Michael

2.621.606 ₫

3.014.847 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A parking lot with a building in the background.

A motel with a large parking lot and multiple rooms.

A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

17. Clinton Motel

Clinton

Selena

2.021.604 ₫

2.324.845 ₫ total

includes taxes & fees

14 Sept - 15 Sept

Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

A train traveling along a river with autumn foliage in the background.

18. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Carolyn

2.114.650 ₫

2.431.886 ₫ total

includes taxes & fees

17 Sept - 18 Sept

An outdoor dining area with trees and tables under string lights.

A living room with a fireplace, a television mounted above it, and a dining area in the background.

A white house with a sign reading "The 1770 House Restaurant & Inn."

A garden pathway leading to a white picket fence and a building with an American flag.

19. The 1770 House Restaurant & Inn

East Hampton

Lisa

12.667.423 ₫

17.317.112 ₫ total

includes taxes & fees

21 Sept - 22 Sept

A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.

A hotel room with a bed, a small table, a chair, a painting on the wall, and a window with a curtain.

A sign for Lamplighter Motel with a 'VACANCY' sign next to it.

20. Lamplighter Motel - Clinton, Connecticut

Clinton

Steven

1.788.342 ₫

2.056.593 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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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 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 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 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 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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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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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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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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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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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

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Deverian actualizar las tv’s"

The Atlantic Hotel

8/10 Good

"This property is a lovely option if you want to be near to central Southampton but not in the middle of it. the room was really nicely appointed, they have a lovely grounds area near the pool, and a really nice pool deck with a pretty big heated pool. We really enjoyed the pool. Only negative is that It's located on a 2 lane highway without much close buy in the way of restaurants or other necessities; getting around was awkward and costly without a car. However, the place we stayed at was nice!"

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Everything went smoother than I thought it would. The staff couldn’t have been kinder, helpful, or more knowledgeable. The spa treatments and massages were off the charts! We’re looking forward to our next stay and many more to come!"

Ocean Surf Resort

10/10 Excellent

"Staff friendly. Room clean and comfortable"

Offshore Montauk

10/10 Excellent

"Everything"

Montauk Manor

10/10 Excellent

"Excellent service, beautiful property, accommodating staff."

Faraway Sag Harbor

8/10 Good

"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."