Book The Best Hotels in Dering Harbor, NY for 2026 from CA $126 - Fully Refundable Options

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Our top choices for Dering Harbor hotels

The entrance to The Harbor Front Inn with a double door and the address number 209.

1. The Harbor Front Inn

Greenport

Laura

CA $251 total

includes taxes & fees

Nov 18 - Nov 19

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

2. Zey Hotel

Greenport

Renee

CA $245 total

includes taxes & fees

Nov 10 - Nov 11

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

3. Sound View Greenport

Greenport

Christine

CA $284 total

includes taxes & fees

Nov 15 - Nov 16

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

4. The Chequit

The Heights

Patrick

CA $272 total

includes taxes & fees

Nov 19 - Nov 20

A beachside outdoor seating area with white Adirondack chairs and a fire pit.

5. Silver Sands Motel & Beach Bungalows

Greenport

Becky

CA $387 total

includes taxes & fees

Nov 2 - Nov 3

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

6. The Shoals Suites and Slips

Southold

Masayo

CA $298 total

includes taxes & fees

Nov 10 - Nov 11

A balcony with a view of the ocean, a lawn, and a house in the background.

7. Cliffside Resort Condominiums

Greenport

William

CA $425 total

includes taxes & fees

Nov 12 - Nov 13

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

8. Oyster Estate

Greenport

Allison

CA $374 total

includes taxes & fees

Nov 8 - Nov 9

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

9. House on Chase Creek

The Heights

Tracey

CA $296 total

includes taxes & fees

Nov 3 - Nov 4

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

10. Sag Harbor Inn

Sag Harbor

Terri

CA $350 total

includes taxes & fees

Nov 1 - Nov 2

11. Shelter Island House

Shelter Island Heights

Kate

CA $542 total

includes taxes & fees

Oct 30 - Oct 31

A modern interior with a central water feature, shelves with products, and a clothing rack.

12. American Beech Hotel

Greenport

Mary

CA $457 total

includes taxes & fees

Nov 1 - Nov 2

A parking lot with a building in the background.

13. Clinton Motel

Clinton

Kalev

CA $126 total

includes taxes & fees

Nov 1 - Nov 2

14. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Kevin

CA $132 total

includes taxes & fees

Nov 15 - Nov 16

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

15. The Bentley Hotel Southampton

Southampton

Armando

CA $230 total

includes taxes & fees

Nov 7 - Nov 8

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

16. The Menhaden

Greenport

Daniel

CA $582 total

includes taxes & fees

Nov 15 - Nov 16

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

17. Faraway Sag Harbor

Sag Harbor

Thomas

CA $562 total

includes taxes & fees

Nov 16 - Nov 17

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

18. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Susan

CA $156 total

includes taxes & fees

Nov 29 - Nov 30

19. Motel 6 Old Saybrook, CT

Old Saybrook

David

CA $112 total

includes taxes & fees

Nov 4 - Nov 5

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

20. North Fork Resort

Greenport

Altynai

CA $497 total

includes taxes & fees

Nov 1 - Nov 2

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Top Dering Harbor Hotel Reviews

The Harbor Front Inn

10/10 Excellent

"Such a lovely place for a getaway. Charming town and lovely water views!"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

More cheap stays in Dering Harbor

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

CA $115

CA $132 total

Nov 15 - Nov 16

includes taxes & fees

8/10 Very good! (1,001 reviews)

Hotels in Dering Harbor with star rating

Frequently asked questions

When is the best time to go to Dering Harbor?

The best time to visit Dering Harbor is during the summer months, from June to August, when the weather is warm and sunny, great for enjoying all the outdoor activities the area offers.

During this period, visitors can fully experience the charm of Dering Harbor, with its pleasant temperatures ideal for sailing, swimming, and exploring the local beaches. The days are long, allowing for extended outings and enjoying the natural beauty of the area.

Couples looking for a romantic getaway will find these months particularly appealing. They can enjoy sunset cruises, leisurely strolls along the waterfront, and dining at outdoor restaurants. The warm evenings provide a lovely setting for a relaxing break.

Families also benefit greatly from a summer visit. The calm waters are ideal for children to swim and play, and many local establishments cater to family-friendly activities.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Dering Harbor.

How much is the nightly rate at a Dering Harbor hotel?

Prices for hotels in Dering Harbor often vary, but you can find a great deal from CA $126 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Our top choices for Dering Harbor hotels

1. The Harbor Front Inn

2. Zey Hotel

3. Sound View Greenport

4. The Chequit

5. Silver Sands Motel & Beach Bungalows

6. The Shoals Suites and Slips

7. Cliffside Resort Condominiums

8. Oyster Estate

9. House on Chase Creek

10. Sag Harbor Inn

11. Shelter Island House

12. American Beech Hotel

13. Clinton Motel

14. Pier Blue Inn Old Saybrook - Essex

15. The Bentley Hotel Southampton

16. The Menhaden

17. Faraway Sag Harbor

18. Quality Inn Old Saybrook - Westbrook

19. Motel 6 Old Saybrook, CT

20. North Fork Resort

Top Dering Harbor Hotel Reviews

The Harbor Front Inn

More cheap stays in Dering Harbor

Pier Blue Inn Old Saybrook - Essex

Hotels in Dering Harbor with star rating

Frequently asked questions

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