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 kitchen counter with a bottle of wine, a glass, and a basket of snacks.

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

1. The Harbor Front Inn

Greenport

Antrii

4.073.895 ₫

5.393.159 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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.

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

2. Silver Sands Motel & Beach Bungalows

Greenport

Keith

7.242.480 ₫

8.274.533 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

3. Sag Harbor Inn

Sag Harbor

Terri

5.664.654 ₫

6.471.868 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

4. Sound View Greenport

Greenport

Christine

4.481.284 ₫

5.858.600 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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

A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

5. The Menhaden

Greenport

Daniel

8.507.327 ₫

10.754.306 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

A spacious living room with a fireplace, comfortable seating, and large windows.

A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

6. Faraway Sag Harbor

Sag Harbor

Thomas

9.078.966 ₫

11.409.947 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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.

7. Zey Hotel

Greenport

Renee

4.714.078 ₫

5.385.835 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.

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.

8. Oyster Estate

Greenport

Allison

5.819.850 ₫

7.332.817 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

9. American Beech Hotel

Greenport

Mary

6.487.193 ₫

8.446.025 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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 living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

10. The Shoals Suites and Slips

Southold

Masayo

4.797.885 ₫

6.128.235 ₫ total

includes taxes & fees

26 Oct - 27 Oct

11. Cliffside Resort Condominiums

Greenport

William

4.371.871 ₫

7.864.557 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A modern bathroom with a white sink, black faucet, and a large mirror. There is a toilet with a basket on the tank and a shelf above it. A glass shower enclosure is visible to the right.

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.

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

12. North Fork Resort

Greenport

Altynai

8.310.746 ₫

9.495.027 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A staircase with wooden balusters and a white wall.

13. The Chequit

The Heights

Patrick

4.632.601 ₫

5.292.747 ₫ total

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 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.

14. House on Chase Creek

The Heights

Tracey

4.781.589 ₫

5.462.899 ₫ total

includes taxes & fees

2 Nov - 3 Nov

15. Shelter Island House

Shelter Island Heights

Dorothy

5.205.533 ₫

5.947.111 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

A spacious lobby with a fireplace, a round table with a vase of flowers, and a reception desk.

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

16. Water's Edge Resort & Spa

Westbrook Center

Laurie

4.865.395 ₫

6.041.393 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

A modern hotel room with a bed, bedside table, and a view of the garden.

A large, white, two-story building with a covered porch and a bicycle parked in front.

A bar area with shelves stocked with various bottles and glasses.

17. Topping Rose House

Bridgehampton

Adam

16.179.183 ₫

18.575.247 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

18. Saybrook Point Resort & Marina

Old Saybrook Center

Jenny

7.216.614 ₫

9.204.416 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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 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.

19. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Amy

2.506.415 ₫

2.882.377 ₫ total

includes taxes & fees

15 Nov - 16 Nov

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

A bathtub surrounded by candles and flower petals.

A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

20. A Room At The Beach

Bridgehampton

Samantha

7.658.923 ₫

8.750.210 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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Top Dering Harbor Hotel Reviews

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."

The Bentley Hotel Southampton

10/10 Excellent

"Perfect one day stay. I would stay here again and can recommend it to others."

The Hampton Maid

10/10 Excellent

"The rooms were well appointed. Spacious rooms. Beds were very comfortable with nice cotton linens. Complimentary bottled water was appreciated. My son loved the playground. Would like to come back when the pool is open. There was only a few things missing, such a hair dryer and slippers. We did ask for a small step stool for my son so he can reach the sink to brush his teeth but they did seem to have one on the premise. Breakfast service was poor."

Zey Hotel

10/10 Excellent

"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly and accommodating. We had a great time checking out all the cool lounge areas in the hotel. The room was clean and charming as well. Would definitely stay here again the next time we visit Greenport"

Water's Edge Resort & Spa

10/10 Excellent

"Great"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"

Sag Harbor Inn

10/10 Excellent

"The hotel was beautiful. The room was very spacious and comfortable. The continental breakfast offered many choices, and they had coffee, tea and hot chocolate available 24 hours a day."

Quality Inn Old Saybrook - Westbrook

8/10 Good

"Room was spacious, comfortable and clean. Overall the hotel was nice. The decorating was a bit off putting and looked like it had been done in the 1970’s and never changed; orange and avocado green with brown carpet. If you can get past that it was a good place to stay. Breakfast was very nice with plenty of hot and cold choices. For me, the fact that it was open from 7:30 til 10 am was very nice. I would stay here again."

The Harbor Front Inn

8/10 Good

"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice hotel"

More cheap stays in Dering Harbor

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

2.113.511 ₫

2.430.628 ₫ total

15 Nov - 16 Nov

includes taxes & fees

8/10 Very good! (1,002 reviews)

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

2.506.415 ₫

2.882.377 ₫ total

15 Nov - 16 Nov

includes taxes & fees

Shorewood Inn

1399 Main Rd Riverhead NY

2.653.852 ₫

3.031.754 ₫ total

25 Oct - 26 Oct

includes taxes & fees

The Atlantic Hotel

1655 County Road 39 Southampton NY

2.770.249 ₫

3.811.661 ₫ total

28 Oct - 29 Oct

includes taxes & fees

7.2/10 Good! (1,000 reviews)

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

3.621.240 ₫

4.137.268 ₫ total

10 Nov - 11 Nov

includes taxes & fees

9.6/10 Exceptional! (605 reviews)

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY

6.867.423 ₫

7.846.192 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Frequently asked questions

What's the seasonal weather in Dering Harbor?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Dering Harbor is 1448 mm.

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Find hotels in Dering Harbor, NY from 2.264.776 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Dering Harbor

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Dering Harbor hotels

1. The Harbor Front Inn

2. Silver Sands Motel & Beach Bungalows

3. Sag Harbor Inn

4. Sound View Greenport

5. The Menhaden

6. Faraway Sag Harbor

7. Zey Hotel

8. Oyster Estate

9. American Beech Hotel

10. The Shoals Suites and Slips

11. Cliffside Resort Condominiums

12. North Fork Resort

13. The Chequit

14. House on Chase Creek

15. Shelter Island House

16. Water's Edge Resort & Spa

17. Topping Rose House

18. Saybrook Point Resort & Marina

19. Quality Inn Old Saybrook - Westbrook

20. A Room At The Beach

Top Dering Harbor Hotel Reviews

Faraway Sag Harbor

The Bentley Hotel Southampton

The Hampton Maid

Zey Hotel

Water's Edge Resort & Spa

Pier Blue Inn Old Saybrook - Essex

Sag Harbor Inn

Quality Inn Old Saybrook - Westbrook

The Harbor Front Inn

More cheap stays in Dering Harbor

Pier Blue Inn Old Saybrook - Essex

Quality Inn Old Saybrook - Westbrook

Shorewood Inn

The Atlantic Hotel

The Bentley Hotel Southampton

Hampton's Vacation Inn

Frequently asked questions

Explore a world of travel with Expedia

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