Dering Harbor Holiday Rentals, Shelter Island: Private House Rentals

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

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

A residential area with a large building, a swimming pool, and a dock extending into a body of water.

1. The Harbor Front Inn

Greenport

Michael

฿8,555

฿10,714 total

includes taxes & fees

4 Oct - 5 Oct

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

A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

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

A bar area with stools, a shelf with glasses, and decorative plants.

2. Zey Hotel

Greenport

Renee

฿5,551

฿6,341 total

includes taxes & fees

15 Sept - 16 Sept

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

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

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

3. The Pridwin Hotel

Shelter Island Heights

Anna

฿16,675

฿20,956 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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.

4. The Menhaden

Greenport

Lisa

฿12,996

฿16,164 total

includes taxes & fees

13 Sept - 14 Sept

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.

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

5. Silver Sands Motel & Beach Bungalows

Greenport

Sirikhwan

฿11,043

฿12,617 total

includes taxes & fees

28 Sept - 29 Sept

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 seaside restaurant with outdoor seating, a deck, and a view of the ocean.

6. Sound View Greenport

Greenport

Irene

฿9,621

฿13,810 total

includes taxes & fees

28 Sept - 29 Sept

7. Cliffside Resort Condominiums

Greenport

Christine

฿9,600

฿13,900 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

8. North Fork Resort

Greenport

Lisa

฿11,742

฿13,416 total

includes taxes & fees

10 Sept - 11 Sept

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".

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

9. American Beech Hotel

Greenport

Mary

฿8,848

฿11,425 total

includes taxes & fees

9 Sept - 10 Sept

A poolside area with lounge chairs and yellow umbrellas.

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

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

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

10. Oyster Estate

Greenport

Jenny

฿11,315

฿14,256 total

includes taxes & fees

5 Oct - 6 Oct

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 sign for 'House on Chase Creek' with a duck illustration.

11. House on Chase Creek

The Heights

Calvin

฿7,081

฿8,090 total

includes taxes & fees

5 Oct - 6 Oct

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

A staircase with wooden balusters and a white wall.

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

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

12. The Chequit

The Heights

Kristin

฿6,809

฿7,779 total

includes taxes & fees

4 Oct - 5 Oct

13. Shelter Island House

Shelter Island Heights

Dorothy

฿6,625

฿7,569 total

includes taxes & fees

4 Oct - 5 Oct

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 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.

14. The Shoals Suites and Slips

Southold

Melissa

฿6,638

฿8,407 total

includes taxes & fees

1 Oct - 2 Oct

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

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

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.

15. West Neck Guesthouse

Shelter Island Heights

Allie

฿10,320

฿11,791 total

includes taxes & fees

9 Sept - 10 Sept

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

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

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.

16. Sag Harbor Inn

Sag Harbor

Loretta

฿10,657

฿12,176 total

includes taxes & fees

4 Oct - 5 Oct

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

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

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.

17. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Theresa

฿3,327

฿3,826 total

includes taxes & fees

4 Oct - 5 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 hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

18. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Carolyn

฿2,806

฿3,227 total

includes taxes & fees

10 Sept - 11 Sept

A marina with boats docked, a fire pit table, and outdoor seating.

An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.

A two-story Victorian-style house with a balcony, a porch, and a small tower.

19. Saybrook Point Resort & Marina

Old Saybrook Center

Florence

฿11,479

฿14,352 total

includes taxes & fees

4 Oct - 5 Oct

A living room with a stone fireplace, grey sofas, and a coffee table.

A large, two-story house with a wrap-around porch, multiple windows, and a chimney.

A dining room with a wooden table, six chairs, and a large window with curtains.

A bedroom with a large bed, a nightstand, a dresser, and a robe rack.

20. The Captain Stannard

Westbrook Center

Deborah

฿7,694

฿8,540 total

includes taxes & fees

13 Sept - 14 Sept

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Top Dering Harbor Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Good location. Clean room. Friendly staff. Need towels by the sink. Coffee maker, but no coffee."

Shorewood Inn

10/10 Excellent

"While initially I was struck that it is not an Inn by looks like a motel. HOWEVER, the he owners are so lovely and sweet. It is in walking distance of a nic restaurant as well as coffee etc. The grounds ar nicely maintained with pretty flowers and plants. And there are chickens!!! Mad sitting area in th back with furniture and lots of grass."

Hampton's Vacation Inn

10/10 Excellent

"Wonderful stay!! Loved this property and the staff. Clean, well kept. Beds were slightly uncomfortable but that wasn’t a big deal. Great location!"

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Water's Edge Resort & Spa

8/10 Good

"Excellent staff and location. The food was mediocre"

Sound View Greenport

10/10 Excellent

"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city and enjoy some quiet time by the water. Greenport is also nearby, making it convenient to explore the local restaurants, shops, vineyards, and other attractions. If you’re planning a trip to Greenport or the North Fork, Sound View is definitely a place worth considering. I would happily stay here again! 🌅🌊❤️"

The Hampton Maid

10/10 Excellent

"Absolutely beautiful hotel, in peaceful setting with lovely amenities."

Sag Harbor Inn

10/10 Excellent

"Sag Harbor Inn was located in a beautiful spot and close to shops and restaurants. This was an excellent choice."

North Fork Resort

8/10 Good

"My sisters and I booked a 2 bedroom cottage for a long weekend around Greenport. The listing said it was a 2 bedroom with queen beds but when I arrived I realized one room was only a full so one of us had to sleep on the pull out couch for us all to be comfortable. You also definitely need a car. It’s a 45 min walk from the train station so if you’re coming from the city it’s not a convenient location and it’s off a busy road. The cottage did have lots of kitchen amenities and a grill which is great if you’re looking for some easy meals. The shower’s water pressure was great and the air conditioning was effective. Unfortunately you can’t open any windows because there are no screens in the windows and the area is buggy. Overall, the place was nice but the rooms are smaller than I expected and you’re far from everything (even the main reception and pool)"