Hotels in Dering Harbor

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Oct 31 - Nov 1
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Nov 1 - Nov 2
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Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

Where to stay in Dering Harbor?

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

1. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (673 reviews)
Overlooking Greenport Harbor, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness center, and complimentary breakfast while exploring nearby attractions.
The price is $138
$186 total
includes taxes & fees
Nov 16 - Nov 17
The Harbor Front Inn
A two-story house with a balcony, outdoor seating area, and a variety of plants.

2. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (440 reviews)
Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbor. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbor Brewing Company and Farmers' Market.
The price is $180
$206 total
includes taxes & fees
Nov 1 - Nov 2
Zey Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.

3. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (762 reviews)
Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railroad Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.
The price is $152
$203 total
includes taxes & fees
Nov 15 - Nov 16
Sound View Greenport
An outdoor patio area with string lights, tables, chairs, and a fire pit.

4. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (75 reviews)
Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.
The price is $181
$207 total
includes taxes & fees
Nov 19 - Nov 20
The Chequit
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

5. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (349 reviews)
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.
The price is $206
$260 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
A serene landscape with a calm body of water reflecting trees with autumn foliage.

6. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
Overlooking Chase Creek, this inviting guesthouse sits adjacent to a golf course in tranquil Shelter Island Heights. Free WiFi and parking enhance your stay while the garden and terrace offer peaceful spots to unwind near Shelter Island Country Club.
The price is $185
$211 total
includes taxes & fees
Nov 9 - Nov 10
House on Chase Creek
A bedroom with a large bed, a desk, a chair, and a view of the outdoors.

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (187 reviews)
The price is $250
$286 total
includes taxes & fees
Dec 1 - Dec 2
Silver Sands Motel & Beach Bungalows
A cozy interior with a bar area, seating, and a fireplace.

8. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (301 reviews)
Unwind at this North Fork retreat with a refreshing swim or soothing soak after exploring nearby museums. Complimentary bikes let you discover charming Greenport while free WiFi and parking add convenience to your coastal escape.
The price is $225
$284 total
includes taxes & fees
Nov 8 - Nov 9
Oyster Estate
A balcony with a view of the ocean, a lawn, and a house in the background.

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (298 reviews)
The price is $212
$353 total
includes taxes & fees
Nov 9 - Nov 10
Cliffside Resort Condominiums
A waterfront property with a large house, multiple boats docked, and lush greenery.

10. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (682 reviews)
Wake up to complimentary breakfast at this waterfront hotel, just moments from Sag Harbor Whaling Museum. The outdoor pool offers refreshing relaxation after exploring nearby attractions. Free WiFi and parking enhance the value, while the attentive staff ensures a memorable stay.
The price is $219
$250 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

11. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (195 reviews)
Escape to this stylish Greenport retreat offering free breakfast and WiFi. Relax at the rooftop terrace or grab a drink from the bar before exploring local attractions on complimentary bikes. Only a 3-minute walk from Greenport Station, near Camera Obscura.
The price is $276
$356 total
includes taxes & fees
Dec 1 - Dec 2
The Menhaden
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

12. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
Explore Greenport from this stylish inn with its welcoming bar and restaurant. Grab the complimentary bikes to visit nearby Greenport Harbor Brewing Company. The attentive staff and daily housekeeping ensure a carefree stay, just an 8-minute walk from the train station.
The price is $251
$327 total
includes taxes & fees
Nov 1 - Nov 2
American Beech Hotel
A parking lot with a building in the background.

13. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (344 reviews)
Wake up to seaside charm at this Clinton motel where the ocean beckons nearby. Take a refreshing dip in the seasonal outdoor pool after exploring Clinton Plaza or the historic Adam Stanton House. Free WiFi and parking add value, with Clinton Station just a 19-minute walk away.
The price is $78
$90 total
includes taxes & fees
Nov 1 - Nov 2
Clinton Motel
A sign for Pier Blue Guesthouse with a logo and name.

14. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,006 reviews)
Tucked beside Old Saybrook Station, this peaceful inn offers comfortable beds and free parking. Explore nearby Chalker Beach or hike local trails before relaxing in clean rooms. Himalaya Café and The Teakettle Cafe are just steps away for tasty meals.
The price is $76
$88 total
includes taxes & fees
Nov 1 - Nov 2
Pier Blue Inn Old Saybrook - Essex
A modern house with a deck, outdoor seating, and a fire pit.

15. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (72 reviews)
The price is $321
$367 total
includes taxes & fees
Nov 1 - Nov 2
North Fork Resort
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

16. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,004 reviews)
Relax at this peaceful hotel with an indoor pool and fitness center. Just a short drive from Old Saybrook Station, enjoy American cuisine at The Comfort Cafe and unwind at the bar. Free breakfast, WiFi, and parking add value near popular local attractions.
The price is $97
$111 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Old Saybrook - Westbrook
Room

17. Motel 6 Old Saybrook, CT

Motel 6 Old Saybrook, CT
2.0 star property
Old Saybrook
7.0 out of 10, Good, (952 reviews)
Tranquil accommodations near Tanger Outlets and Crystal Lake Town Park offer a quiet escape. Take advantage of free weekend breakfast, WiFi, and parking. Only a 4-minute drive from Old Saybrook Station for convenient regional travel.
The price is $70
$80 total
includes taxes & fees
Nov 4 - Nov 5
Motel 6 Old Saybrook, CT
A pool area with umbrellas, potted plants, and a pathway leading to a building.

18. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (320 reviews)
Immerse in coastal charm at this Sag Harbor retreat where massages await after beach days. The seasonal outdoor pool offers refreshment while the fitness center keeps routines intact. Friendly staff ensure a memorable stay near historical museums.
The price is $355
$446 total
includes taxes & fees
Nov 16 - Nov 17
Faraway Sag Harbor
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

19. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,000 reviews)
Relax at this coastal Westbrook resort with a private beach, 3 restaurants including Italian cuisine at Dattilo's Fine Dining, and rejuvenating spa services. Near Tanger Outlets and just 9 minutes from Old Saybrook Station.
The price is $190
$236 total
includes taxes & fees
Nov 12 - Nov 13
Water's Edge Resort & Spa
A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.

20. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, Good, (263 reviews)
The price is $69
$79 total
includes taxes & fees
Nov 1 - Nov 2
Lamplighter Motel - Clinton, Connecticut
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Go beyond your typical stay in Dering Harbor

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Check out reviews of Dering Harbor hotels guests love

A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport

10/10 Exceptional

We had a lovely stay.
United States
Nicole
Reviewed June 22, 2024
Silver Sands Motel & Beach Bungalows

Frequently Asked Questions

What accommodations do travelers like in Dering Harbor?

Guests like Sound View Greenport, Zey Hotel and Faraway Sag Harbor.

Can I book a refundable accommodation in Dering Harbor?

If you want the flexibility to change your plans to Dering Harbor, most accommodations offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Dering Harbor be like during my trip?

The warmest months in Dering Harbor are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.

Why should I book my Dering Harbor hotel with Hotels.com?

There are plenty of reasons to book your Dering Harbor travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.