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4 Stars Hotels in Dering Harbor, Shelter Island from CA $431

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Check availability on Dering Harbor 4 Star Hotels

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Dering Harbor 4-star hotels

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

1. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $342
CA $431 total
includes taxes & fees
Oct 14 - Oct 15
Sound View Greenport
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
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.

2. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
CA $594
CA $746 total
includes taxes & fees
Oct 5 - Oct 6
Faraway Sag Harbor
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.
A living room with a fireplace, two sofas, a coffee table, and a chair.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

3. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
CA $376
CA $472 total
includes taxes & fees
Oct 13 - Oct 14
Journey East Hampton
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 beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

4. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Morris
The Pridwin Hotel
A two-story building with a porch and a flagpole.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
A hotel interior with a long corridor, seating areas, and a reception desk.

5. The Maidstone

The Maidstone
East Hampton
United States
Steven
CA $408
CA $489 total
includes taxes & fees
Oct 19 - Oct 20
The Maidstone
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.
A person riding a bicycle under a striped awning with a logo, in front of a building with large windows and a white facade.
A breakfast buffet with various food items and beverages.
A cozy room with a large window, a sofa, a small table with a tray, and a pair of slippers on the floor.

6. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
CA $633
CA $767 total
includes taxes & fees
Oct 5 - Oct 6
Canoe Place Inn and Cottages
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
A grassy area with trees and a view of 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.

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sarah
CA $386
CA $441 total
includes taxes & fees
Oct 18 - Oct 19
Silver Sands Motel & Beach Bungalows
A multi-story hotel with balconies and a beach view.
A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.
A covered porch with a view of the ocean, a wicker chair, and a small table.
A grand staircase with a chandelier, a reception desk, and a fireplace.

8. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
CA $551
CA $634 total
includes taxes & fees
Oct 18 - Oct 19
Madison Beach Hotel
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
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.

9. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
CA $420
CA $529 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.
A bar area with a long counter, multiple stools, and a well-stocked bar.
A large, two-story house with a wrap-around porch and a conservatory.

10. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
CA $390
CA $449 total
includes taxes & fees
Sep 23 - Sep 24
Copper Beech Inn
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar area with shelves stocked with various bottles and glasses.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A modern hotel room with a bed, bedside table, and a view of the garden.

11. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
CA $1,328
CA $1,522 total
includes taxes & fees
Sep 29 - Sep 30
Topping Rose House
A beach with waves gently lapping onto the shore.
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.
A modern bedroom with a bed, a desk with a chair, a television, and a large mirror.
A patio with four wicker chairs arranged around a round table with a fire pit in the center, set in a grassy outdoor area with trees and a fence in the background.

12. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
CA $971
CA $1,165 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.
A white house with a sign reading "The 1770 House Restaurant & Inn."
A living room with a fireplace, a television mounted above it, and a dining area in the background.
A restaurant with wooden beams, tables with white tablecloths, and a bar area.

13. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
CA $635
CA $869 total
includes taxes & fees
Oct 22 - Oct 23
The 1770 House Restaurant & Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.
A beach with a lifeguard tower, a few people sitting on chairs, and a white umbrella.
A sliding glass door leading to an outdoor deck with a view of a swimming pool and greenery.
A large, modern house with a swimming pool, surrounded by lush greenery and trees.

14. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
Clearwater Beach
United States
IVAN
CA $961
CA $1,098 total
includes taxes & fees
Sep 28 - Sep 29
East Hampton Art House Bed & Breakfast
A four-poster bed with a green area rug, a white armchair, a television mounted on the wall, and a chandelier.
A room with a fireplace, a television mounted above it, and a round table with a bowl and a book.
A wooden pier leading into calm waters with sailboats anchored in the distance.
A building labeled 'Little House Brewing Co.' with outdoor seating and a porch.

15. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
Old Saybrook Center
United States
Diane
James Pharmacy Bed & Breakfast
A vase with orange flowers on a table.
A wooden staircase with a dog sign, a blue armchair, and a dining area in the background.
A dining room with a wooden table set for six, surrounded by six chairs. There is a chandelier above the table, and a potted plant on the windowsill.
A two-story house with a front porch, a chimney, and a sign reading "Main Entrance."

16. 434 on Main

434 on Main
Amagansett North
United States
David
434 on Main
A two-story house with a covered porch and a chimney.
A four-poster bed with white bedding, a wooden dresser with multiple drawers, a nightstand with a lamp, and a window with red curtains.
A dining table with a vase of white flowers, surrounded by chairs, in a room with windows and a chandelier.
A round table with a white tablecloth, a glass cake stand with a white cake, a glass decanter, wine glasses, and a bouquet of white flowers.

17. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
Cutchogue
United States
Bent
The Farmhouse Bed and Breakfast

18. The Baker House 1650

The Baker House 1650
East Hampton
United States
Marcelle
The Baker House 1650
A brick pathway leading to a large, two-story building with a symmetrical facade, surrounded by manicured hedges and trees.
An outdoor patio area with tables and chairs, a covered seating area, and a large house in the background.
A restaurant with a long table set for a meal, surrounded by chairs, and a wine rack with bottles.
A gazebo with a dome roof, surrounded by a garden with various flowers and a pathway leading to it.

19. Jedediah Hawkins Inn

Jedediah Hawkins Inn
Jamesport
United States
OMAR
Jedediah Hawkins Inn
A modern kitchen with a central island, bar stools, stainless steel appliances, and wooden flooring.
A living room with a fireplace, two armchairs, a hanging light fixture, and a large window.
A long dining table set for a meal with chairs, a chandelier, and a large abstract painting on the wall.
A patio with a fire pit, outdoor furniture, and a pool.

20. The Mainstay

The Mainstay
Southampton
The Mainstay
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Dering Harbor.
Mill House Inn

Mill House Inn

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CA $1,224
CA $1,769 total
Sep 27 - Sep 28
includes taxes & fees
Mill House Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Dering Harbor Hotel Reviews

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

10/10 Excellent
"Excellent stay. The room was clean and stylish. Can’t wait to come back"
Sarah 1-night trip
Posted 1 day ago
Silver Sands Motel & Beach Bungalows
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 9 days ago
Faraway Sag Harbor

Find out more about Dering Harbor

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Dering Harbor are calling your name. Known for providing first-rate service in amazing locations, each of the Dering Harbor 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Dering Harbor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Dering Harbor, Shelter Island, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Dering Harbor hotels with 4 Stars provide everything you need to unwind in style.

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