Book The Best Hotels in Dering Harbor, NY for 2026 from CA $114 - Fully Refundable Options

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Go beyond your typical stay in Dering Harbor

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Our top choices for Dering Harbor hotels

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

1. Zey Hotel

Greenport

Renee

CA $234

CA $267 total

includes taxes & fees

Sep 14 - Sep 15

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

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

2. The Harbor Front Inn

Greenport

Michael

CA $328

CA $415 total

includes taxes & fees

Oct 4 - Oct 5

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

A beach with sun loungers and umbrellas, a sandy path, 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.

3. Silver Sands Motel & Beach Bungalows

Greenport

Sirikhwan

CA $442

CA $505 total

includes taxes & fees

Oct 12 - Oct 13

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

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.

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

4. The Chequit

The Heights

Kristin

CA $264

CA $302 total

includes taxes & fees

Oct 8 - Oct 9

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

5. Sound View Greenport

Greenport

Irene

CA $335

CA $423 total

includes taxes & fees

Oct 1 - Oct 2

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".

6. The Shoals Suites and Slips

Southold

Melissa

CA $280

CA $355 total

includes taxes & fees

Oct 1 - Oct 2

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 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.

7. House on Chase Creek

The Heights

Calvin

CA $299

CA $341 total

includes taxes & fees

Oct 5 - Oct 6

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

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.

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

8. The Menhaden

Greenport

Lisa

CA $511

CA $640 total

includes taxes & fees

Sep 15 - Sep 16

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

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

9. American Beech Hotel

Greenport

Mary

CA $431

CA $548 total

includes taxes & fees

Sep 21 - Sep 22

10. Shelter Island House

Shelter Island Heights

Dorothy

CA $279

CA $319 total

includes taxes & fees

Oct 4 - Oct 5

A poolside area with lounge chairs and yellow umbrellas.

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

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

11. Oyster Estate

Greenport

Jenny

CA $439

CA $553 total

includes taxes & fees

Oct 13 - Oct 14

12. Cliffside Resort Condominiums

Greenport

Christine

CA $401

CA $582 total

includes taxes & fees

Oct 5 - Oct 6

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 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.

13. North Fork Resort

Greenport

Lisa

CA $411

CA $470 total

includes taxes & fees

Oct 13 - Oct 14

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

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

A restaurant with green booths, wooden chairs, and round tables.

14. The Pridwin Hotel

Shelter Island Heights

Anna

CA $703

CA $884 total

includes taxes & fees

Sep 14 - Sep 15

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

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.

15. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Carolyn

CA $113

CA $130 total

includes taxes & fees

Sep 16 - Sep 17

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

16. West Neck Guesthouse

Shelter Island Heights

Allie

CA $435

CA $497 total

includes taxes & fees

Sep 15 - Sep 16

A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.

A multi-story residential building with blue trim and large windows.

A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.

A tranquil park with a gazebo, a pond with a fountain, and a building in the background.

17. Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Laurie

CA $99

CA $114 total

includes taxes & fees

Sep 27 - Sep 28

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

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

18. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Michael

CA $140

CA $161 total

includes taxes & fees

Oct 4 - Oct 5

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 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.

19. Clinton Motel

Clinton

Selena

CA $108

CA $124 total

includes taxes & fees

Sep 14 - Sep 15

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

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

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

20. Lamplighter Motel - Clinton, Connecticut

Clinton

Steven

CA $96

CA $110 total

includes taxes & fees

Sep 21 - Sep 22

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Top Dering Harbor Hotel Reviews

Water's Edge Resort & Spa

10/10 Excellent

"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Deverian actualizar las tv’s"

The Harbor Front Inn

10/10 Excellent

"This was our first trip to Greenport and we had a fabulous stay. The hotel was perfectly located downtown."

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!"

Quality Inn Old Saybrook - Westbrook

8/10 Good

"Not the usual Marriott standards, but a decent cheap room"

North Fork Resort

10/10 Excellent

"This property is so awesome! Adorable cottages, not very big, but sufficient. We were 2 couples, and we managed. Very quaint an comfortable. Services were provided if asked. They give you everything you need. I may buy in or for sure go back as a guest next year. We loved it, and it's so convenient to town, restaurants, and wineries all around you."

Zey Hotel

10/10 Excellent

"Such an amazing hotel to stay for the weekend"

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."