𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Dering Harbor (2026)

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Go beyond your typical stay in Dering Harbor

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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 hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

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 person standing in front of a building with a sign that reads 'The Harbor Front Inn.'

1. The Harbor Front Inn

Greenport

Antrii

S$270

includes taxes & fees

3 Nov - 4 Nov

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 modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

2. The Chequit

The Heights

Patrick

S$228

includes taxes & fees

1 Nov - 2 Nov

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 beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

3. Sound View Greenport

Greenport

Irene

S$284

includes taxes & fees

3 Nov - 4 Nov

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 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.

4. Zey Hotel

Greenport

Renee

S$267

includes taxes & fees

26 Oct - 27 Oct

A lakeside patio with outdoor seating and a view of the water.

A grassy area with trees and a view of 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.

5. Silver Sands Motel & Beach Bungalows

Greenport

Keith

S$348

includes taxes & fees

1 Nov - 2 Nov

6. Cliffside Resort Condominiums

Greenport

William

S$389

includes taxes & fees

1 Nov - 2 Nov

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 serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

7. House on Chase Creek

The Heights

Tracey

S$270

includes taxes & fees

2 Nov - 3 Nov

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 light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

8. The Shoals Suites and Slips

Southold

Masayo

S$386

includes taxes & fees

1 Nov - 2 Nov

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

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

A tented accommodation with a bed, television, and a small table with a chair.

9. North Fork Resort

Greenport

Harold

S$351

includes taxes & fees

19 Oct - 20 Oct

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

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

A hotel lobby with a sofa, chairs, tables, and a large window.

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

10. Sag Harbor Inn

Sag Harbor

Terri

S$321

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

A dining area with a round table, chairs, a vase, and a painting on the wall.

A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

11. Oyster Estate

Greenport

Allison

S$363

includes taxes & fees

9 Nov - 10 Nov

12. Shelter Island House

Shelter Island Heights

Dorothy

S$294

includes taxes & fees

15 Oct - 16 Oct

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.

13. American Beech Hotel

Greenport

Mary

S$418

includes taxes & fees

19 Oct - 20 Oct

A parking lot with a building in the background.

A motel with a large parking lot and multiple rooms.

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.

14. Clinton Motel

Clinton

Selena

S$115

includes taxes & fees

14 Oct - 15 Oct

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

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

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

15. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Celina

S$113

includes taxes & fees

8 Nov - 9 Nov

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

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

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

16. The Menhaden

Greenport

Daniel

S$557

includes taxes & fees

11 Nov - 12 Nov

A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

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 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.

17. The Bentley Hotel Southampton

Southampton

Doug

S$209

includes taxes & fees

28 Oct - 29 Oct

A room with a leather sofa, a television mounted on the wall, and a window with a decorative frame.

18. Motel 6 Old Saybrook, CT

Old Saybrook

David

S$120

includes taxes & fees

19 Oct - 20 Oct

A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

A bedroom with a bed, a door, and a framed picture on the wall.

A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

A breakfast bar with cereal, coffee, and fresh milk.

19. Shorewood Inn

Riverhead

Dennis

S$150

includes taxes & fees

22 Oct - 23 Oct

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 hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.

A living room with two sofas, a coffee table, a lamp, and a painting on the wall.

20. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Amy

S$143

includes taxes & fees

2 Nov - 3 Nov

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Top Dering Harbor Hotel Reviews

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."

Saybrook Point Resort & Marina

10/10 Excellent

"This was our seventh year back! Beautiful. Luxurious yet still family friendly. We’ll be back again next year!"

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."

The Bentley Hotel Southampton

10/10 Excellent

"WOW What a nice hotel. Perfect location for Hampton Bays & Southampton. Very clean, very modern & very nice"

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."

Zey Hotel

10/10 Excellent

"The hotel was perfect location. Could walk to restaurants and attractions. Would highly recommend this hotel."

Water's Edge Resort & Spa

10/10 Excellent

"Beautiful place. Staff were very helpful and polite."

The Hampton Maid

10/10 Excellent

"Beautiful property. Lovely rooms."

Shorewood Inn

8/10 Good

"Great 👍"

More cheap stays in Dering Harbor