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Oct 14 - Oct 15
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Oct 15 - Oct 16
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Our top choices for Dering Harbor hotels

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A bar area with wooden bar stools and a bookshelf.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A person standing in front of a building with a sign that reads 'The Harbor Front Inn.'

1. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Antrii
CA $229
CA $302 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A large, white building with multiple windows and a prominent tree in the foreground.
A staircase with wooden balusters and a white wall.
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

2. The Chequit

The Chequit
The Heights
United States
Patrick
CA $211
CA $241 total
includes taxes & fees
Nov 8 - Nov 9
The Chequit
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

3. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
CA $244
CA $319 total
includes taxes & fees
Nov 4 - Nov 5
Sound View Greenport
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 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.

4. Zey Hotel

Zey Hotel
Greenport
United States
Renee
CA $259
CA $296 total
includes taxes & fees
Oct 20 - Oct 21
Zey Hotel
A lakeside patio with outdoor seating 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.
A grassy area with trees and a view of a body of water.
Outdoor spa tub

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
CA $328
CA $375 total
includes taxes & fees
Nov 2 - Nov 3
Silver Sands Motel & Beach Bungalows
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
A storefront with a sign reading "THE SHOALS".
A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

6. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Masayo
CA $264
CA $337 total
includes taxes & fees
Nov 8 - Nov 9
The Shoals Suites and Slips
Terrace/patio
Beach
Room
Living area

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
William
CA $240
CA $432 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
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 sign for 'House on Chase Creek' with a duck illustration.
A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

8. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
CA $263
CA $300 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
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.

9. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
CA $311
CA $356 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
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.

10. North Fork Resort

North Fork Resort
Greenport
United States
Harold
CA $342
CA $391 total
includes taxes & fees
Oct 22 - Oct 23
North Fork Resort
Front of property - evening/night
Bar (on property)
Terrace/patio
Property amenity

11. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
CA $286
CA $327 total
includes taxes & fees
Oct 20 - Oct 21
Shelter Island House
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".
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.

12. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
CA $357
CA $464 total
includes taxes & fees
Oct 20 - Oct 21
American Beech Hotel
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.
A dining area with a round table, chairs, a vase, and a painting on the wall.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

13. Oyster Estate

Oyster Estate
Greenport
United States
Allison
CA $320
CA $403 total
includes taxes & fees
Oct 25 - Oct 26
Oyster Estate
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.

14. Clinton Motel

Clinton Motel
Clinton
United States
Selena
CA $111
CA $128 total
includes taxes & fees
Oct 28 - Oct 29
Clinton Motel
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 modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.
A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

15. The Menhaden

The Menhaden
Greenport
United States
Daniel
CA $493
CA $621 total
includes taxes & fees
Nov 12 - Nov 13
The Menhaden
A sign for Pier Blue Guesthouse with a logo and name.
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.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

16. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Celina
CA $110
CA $126 total
includes taxes & fees
Oct 20 - Oct 21
Pier Blue Inn Old Saybrook - Essex
Room
Front of property
Front of property
A room with a leather sofa, a television mounted on the wall, and a window with a decorative frame.

17. Motel 6 Old Saybrook, CT

Motel 6 Old Saybrook, CT
Old Saybrook
United States
David
CA $112
CA $133 total
includes taxes & fees
Oct 20 - Oct 21
Motel 6 Old Saybrook, CT
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.
A breakfast bar with cereal, coffee, and fresh milk.
A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

18. Shorewood Inn

Shorewood Inn
Riverhead
United States
Dennis
CA $146
CA $167 total
includes taxes & fees
Oct 19 - Oct 20
Shorewood Inn
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A living room with two sofas, a coffee table, a lamp, and a painting on the wall.
A dining area with tables and chairs, a clock on the wall, and a counter with food items.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.

19. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Amy
CA $138
CA $159 total
includes taxes & fees
Nov 3 - Nov 4
Quality Inn Old Saybrook - Westbrook
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
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.

20. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Doug
CA $203
CA $232 total
includes taxes & fees
Oct 28 - Oct 29
The Bentley Hotel Southampton
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Top Dering Harbor Hotel Reviews

Zey Hotel

Zey Hotel

10/10 Excellent
"It worked out well for me."
Elizabeth 1-night trip
Posted 3 hours ago
Zey Hotel
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 15 hours ago
Sound View Greenport
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."
Cynthia 7-night trip
Posted 16 hours ago
The Bentley Hotel Southampton
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Only thing I would say is the TV in the room. Every channel was blurry and you couldn’t really see anything."
saymon 2-night trip
Posted 1 day ago
Quality Inn Old Saybrook - Westbrook
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

10/10 Excellent
"Came here for a sisters trip. We had the best time! The hotel staff was so friendly and genuinely helpful. The onsite restaurant, The Boathouse, was a delicious stop for our first night. The grounds are so pretty. They really did an amazing job renovating the property. The room temperature wasn’t the best as there didn’t seem to have working AC. As much as we loved everything, next time I would request a room other than #12 because it’s sandwiched in between Nookies restaurant and a busy corridor. Small inconvenience for an otherwise perfect weekend."
Jolene 2-night trip
Posted 1 day ago
Silver Sands Motel & Beach Bungalows
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"The room was clean and well maintained. The staff was friendly and helpful. It was a great location for the events we had planned. Would definitely return for another stay."
Celina 1-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful place. Staff were very helpful and polite."
Deborah 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Ocean Vista was a very well-maintained property. Staff was very welcoming and pleasant as well as professional. Enjoyed our stay we’ll go back."
JEAN-LUC 2-night trip
Posted 3 days ago
Ocean Vista Resort
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"This hotel was clean, comfy and reasonably priced. Everything worked out well virtually checking in and was perfect for our one night stay. Parking was a little nerve racking since there was no parking on the premise but the street parking worked out well reading the street signs and moving the car when necessary."
Richard 1-night trip
Posted 10 days ago
Hampton Bays Hotel on Main

More cheap stays in Dering Harbor

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
CA $110
CA $126 total
Oct 20 - Oct 21
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT
CA $138
CA $159 total
Nov 3 - Nov 4
includes taxes & fees
7.8/10 Good! (1,007 reviews)
Quality Inn Old Saybrook - Westbrook
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $152
CA $210 total
Oct 28 - Oct 29
includes taxes & fees
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $203
CA $232 total
Oct 28 - Oct 29
includes taxes & fees
9.6/10 Exceptional! (600 reviews)
The Bentley Hotel Southampton
Hampton's Vacation Inn

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY
CA $212
CA $242 total
Oct 15 - Oct 16
includes taxes & fees
9/10 Wonderful! (418 reviews)
Hampton's Vacation Inn
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
CA $301
CA $344 total
Oct 20 - Oct 21
includes taxes & fees
The Hampton Maid

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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