Shelter Island Holiday Rentals, New York: Private House Rentals

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Our top choices for Shelter Island hotels

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

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 large building with multiple floors, surrounded by a residential area with houses and a body of water.

A wooden pier extending into a body of water with a cloudy sky above.

1. The Harbor Front Inn

Greenport

Jordan

5.826.600 ₫

7.399.449 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

2. House on Chase Creek

The Heights

Calvin

5.597.280 ₫

6.394.960 ₫ total

includes taxes & fees

5 Oct - 6 Oct

3. Shelter Island House

Shelter Island Heights

Dorothy

5.232.500 ₫

5.977.920 ₫ 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.

4. Silver Sands Motel & Beach Bungalows

Greenport

Sarah

8.450.000 ₫

9.654.320 ₫ total

includes taxes & fees

18 Oct - 19 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 living room with a beige sofa, a coffee table, and a dining table set with plates and glasses.

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

5. West Neck Guesthouse

Shelter Island Heights

Allie

8.151.000 ₫

9.312.680 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A poolside area with lounge chairs and yellow umbrellas.

A cozy interior with a bar area, seating, and a fireplace.

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.

6. Oyster Estate

Greenport

Elizabeth

8.216.000 ₫

10.351.641 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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 staircase with wooden balusters and a white wall.

A large, white building with multiple windows and a prominent tree in the foreground.

7. The Chequit

The Heights

Kristin

5.382.000 ₫

6.148.935 ₫ total

includes taxes & fees

4 Oct - 5 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 reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

8. The Menhaden

Greenport

Lisa

8.671.520 ₫

10.947.040 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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

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.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

9. Sag Harbor Inn

Sag Harbor

Terri

8.424.000 ₫

9.624.420 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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".

10. The Shoals Suites and Slips

Southold

Melissa

5.247.450 ₫

6.645.211 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

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

11. Zey Hotel

Greenport

Renee

4.387.500 ₫

5.012.721 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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.

12. American Beech Hotel

Greenport

Mary

5.954.000 ₫

7.842.640 ₫ total

includes taxes & fees

1 Oct - 2 Oct

13. Cliffside Resort Condominiums

Greenport

Christine

7.183.540 ₫

11.092.120 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

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

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

14. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Michael

2.784.600 ₫

3.202.290 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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 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 a deck extending over the water, featuring large windows and a dining area.

15. Sound View Greenport

Greenport

Irene

6.506.500 ₫

8.176.237 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

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

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

16. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Russell

2.121.340 ₫

2.439.580 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A parking lot with a building in the background.

A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.

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

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

17. Clinton Motel

Clinton

Selena

2.054.000 ₫

2.362.100 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.

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

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

18. The Sagaponack

Wainscott

Jane

5.652.794 ₫

7.497.993 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

19. Faraway Sag Harbor

Sag Harbor

Miguel

10.998.000 ₫

13.821.797 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

A restaurant with wooden beams, tables with white tablecloths, and a bar area.

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

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

20. The 1770 House Restaurant & Inn

East Hampton

Lisa

11.810.500 ₫

16.145.480 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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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 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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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

Ocean Vista Resort

10/10 Excellent

"Staff was very friendly room was clean bed was comfortable"

Zey Hotel

10/10 Excellent

"Lovely hotel, great location and lovely courtyard!"

Water's Edge Resort & Spa

8/10 Good

"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."

Ocean Surf Resort

10/10 Excellent

"it was a lovely stay at the Ocean surf resort. We went in September and the weather was spectacular. We really enjoyed watching the sea life from the deck. We saw so many whales, dolphins and seals too. It was quiet enough to get a night's sleep and the mattress was pretty good too. My only issue was the kitchenette- which was there but not usable. There is no counter space at all. I really think that the rooms need to be reconfigured. There was a nice working little fridge. We never used the stove top (I think that it should be taken out) or just mount the microwave. But all in all, we would stay here again."

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!"

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!"

Beachcomber Resort at Montauk

10/10 Excellent

"The views from the upper level of Building 400 are the best! So tranquil with a clear view of the ocean! The room we stayed in this year was a little dated furniture and appliance wise. Bathroom was updated! The property is very well maintained and the heated pool is great! Would highly recommend staying at The Beachcomber!!"

Ocean Resort Inn

10/10 Excellent

"Closest to beach and town"

Hotel Corduroy

10/10 Excellent

"Loved this hotel. Super clean, cute, comfy rooms. Loved the yard with the couches and fire pits. Would definitely come again."

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

2.121.340 ₫

2.439.580 ₫ total

29 Sept - 30 Sept

includes taxes & fees

Budget Host East End

30 Lake Avenue Riverhead NY

2.314.000 ₫

2.643.746 ₫ total

27 Sept - 28 Sept

includes taxes & fees

6.8/10 (893 reviews)

The Atlantic Hotel

1655 County Road 39 Southampton NY

2.515.500 ₫

3.523.961 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Ocean Surf Resort

84 South Emerson Avenue Montauk NY

2.834.000 ₫

4.368.846 ₫ total

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (323 reviews)

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

4.121.558 ₫

5.358.880 ₫ total

5 Oct - 6 Oct

includes taxes & fees

9.6/10 Exceptional! (589 reviews)

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY

5.499.000 ₫

6.282.608 ₫ total

13 Oct - 14 Oct

includes taxes & fees

Hotels in Shelter Island with star rating

Frequently asked questions

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.

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Book Hotels in Shelter Island on Expedia.com

Find hotels in Shelter Island, NY from 2.004.197 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Shelter Island

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Shelter Island hotels

1. The Harbor Front Inn

2. House on Chase Creek

3. Shelter Island House

4. Silver Sands Motel & Beach Bungalows

5. West Neck Guesthouse

6. Oyster Estate

7. The Chequit

8. The Menhaden

9. Sag Harbor Inn

10. The Shoals Suites and Slips

11. Zey Hotel

12. American Beech Hotel

13. Cliffside Resort Condominiums

14. Quality Inn Old Saybrook - Westbrook

15. Sound View Greenport

16. Pier Blue Inn Old Saybrook - Essex

17. Clinton Motel

18. The Sagaponack

19. Faraway Sag Harbor

20. The 1770 House Restaurant & Inn

Where to stay in Shelter Island

Silver Beach

Menantic Creek

Coecles Harbor

Hay Beach

Shorewood

Stay near popular Shelter Island attractions

Shell Beach

Wades Beach

Mashomack Preserve

Shelter Island Historical Society

Gardiner's Bay Country Club

Menhadden Lane Beach

Havens House

Learn more about Shelter Island

Top Shelter Island Hotel Reviews

Ocean Vista Resort

Zey Hotel

Water's Edge Resort & Spa

Ocean Surf Resort

Montauk Manor

Montauk Yacht Club

Beachcomber Resort at Montauk

Ocean Resort Inn

Hotel Corduroy

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Budget Host East End

The Atlantic Hotel

Ocean Surf Resort

The Bentley Hotel Southampton

The Hampton Maid

Hotels in Shelter Island with star rating

Frequently asked questions

Explore a world of travel with Expedia

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