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Southold LIRR Station Sparkling Pointe Henry W. Prince Building Samuel Landon House Town Doctors' House and Site Custer Observatory Goldsmith's Inlet Park Osprey's Dominion Vineyards Congregation Tifereth Israel Synagogue Union Chapel Shelter Island Country Club Greenport Farmers' Market Island's End Golf and Country Club Old House Manhanset Chapel Lavender by the Bay Fort Corchaug Archeological Site

147 hotels

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Heron Suites at Port of Egypt MarineSouthold- Show on map

Very Good, 8.0

(146reviews)

Swimming pool
Wi-Fi

Avg. price/night

$233

Southold Beach MotelSouthold- Show on map

6.8

(80reviews)

Garden
Wi-Fi

Avg. price/night

$181

Shorecrest Bed and BreakfastSouthold- Show on map

Exceptional, 10.0

(13reviews)

Pet friendly
Private beach
Garden
Concierge
Bicycle rental
Wi-Fi

Avg. price/night

$687

Historic White Blossom HouseSouthold- Show on map

Garden
Wi-Fi

Wickham-Prince Bed and BreakfastSouthold- Show on map

Garden

Sound View GreenportSouthold- Show on map

Very Good, 8.4

(735reviews)

Restaurant
Fitness center
Swimming pool
Spa
Private beach
Wi-Fi
Parking

Avg. price/night

$280

The Cliffside Resort CondominiumsGreenport West- Show on map

Very Good, 8.1

(267reviews)

Pet friendly
Swimming pool
Private beach
Wi-Fi

Avg. price/night

$338

North Fork Bayview Vacation Rental Southold- Show on map

Fitness center
Spa

The Pridwin HotelShelter Island Heights- Show on map

Good, 7.3

(275reviews)

Bar
Swimming pool
Babysitting
Wi-Fi

A Walk in the Woods Bed and BreakfastSouthold- Show on map

Very Good, 8.0

(20reviews)

Bicycle rental
Wi-Fi

Avg. price/night

$301

North Fork Guest HouseCutchogue- Show on map

Exceptional, 9.9

(129reviews)

Wi-Fi

Harbor Knoll Bed and BreakfastGreenport- Show on map

Swimming pool
Wi-Fi

Avg. price/night

$476

Sunset BeachShelter Island Heights- Show on map

6.0

(133reviews)

Room service
Pet friendly
Private beach
Babysitting
Wi-Fi

The Inn at Harbor Knoll Greenport- Show on map

Avg. price/night

$432

The Menhaden Hotel Greenport- Show on map

24-Hour reception
Wi-Fi

Avg. price/night

$441

Greenporter HotelGreenport- Show on map

Very Good, 8.0

(348reviews)

Avg. price/night

$199

The Harborfront InnGreenport- Show on map

Superb, 9.0

(304reviews)

Room service
Swimming pool
Concierge
Elevator / Lift
24-Hour reception
Wi-Fi

Avg. price/night

$243

Seven - a boutique B&B on Shelter IslandShelter Island Heights- Show on map

Exceptional, 9.9

(94reviews)

Swimming pool
Garden
Bicycle rental
Parking

Avg. price/night

$382

Greenport Captain's House Greenport- Show on map

Shelter Island HouseShelter Island Heights- Show on map

Fabulous, 8.7

(25reviews)

Room service
Swimming pool
Spa
Garden
Wi-Fi

Avg. price/night

$401

Fordham HouseGreenport- Show on map

Exceptional, 10.0

(235reviews)

Wi-Fi

Townsend Manor InnGreenport- Show on map

6.0

(92reviews)

Restaurant
Swimming pool
Private beach
Child pool
Wi-Fi

Avg. price/night

$156

American Beech HotelGreenport- Show on map

Very Good, 8.3

(53reviews)

Wi-Fi

Avg. price/night

$352

Gallery Hotel Greenport Greenport- Show on map

Wi-Fi

Avg. price/night

$256

Ruby's Cove Greenport- Show on map

The ChequitShelter Island Heights- Show on map

Superb, 9.2

(180reviews)

Garden
24-Hour reception
Wi-Fi
Parking

House on Chase CreekShelter Island Heights- Show on map

Superb, 9.3

(20reviews)

Room service
Garden
24-Hour reception
Bicycle rental
Wi-Fi

Avg. price/night

$128

West Neck GuesthouseShelter Island Heights- Show on map

Superb, 9.4

(8reviews)

Room service
Garden
Wi-Fi

Sweet Dreams Bed and Breakfast Cutchogue Cutchogue- Show on map

The Stirling House B&B GreenportGreenport- Show on map

Superb, 9.4

(279reviews)

Garden
Concierge
Bicycle rental
Wi-Fi

Avg. price/night

$251

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