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Custer Observatory Sparkling Pointe Henry W. Prince Building Southold LIRR Station Joseph Nelson Hallock House Osprey's Dominion Vineyards Goldsmith's Inlet Park Horton Point Light Joshua Wells House Old House Shelter Island Country Club Union Chapel David Tuthill Farmstead Congregation Tifereth Israel Synagogue Fort Corchaug Archeological Site Greenport Farmers' Market Manhanset Chapel Island's End Golf and Country Club Foster Memorial Beach

141 hotels

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Southold Beach MotelSouthold- Show on map

6.8

(80reviews)

Garden
Wi-Fi

Avg. price/night

$181

North Fork Guest HouseCutchogue- Show on map

Exceptional, 9.9

(129reviews)

Wi-Fi

North Fork Bayview Vacation Rental Southold- Show on map

Fitness center
Spa

Wickham-Prince Bed and BreakfastSouthold- Show on map

Garden

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

Very Good, 8.0

(20reviews)

Bicycle rental
Wi-Fi

Avg. price/night

$301

Historic White Blossom HouseSouthold- Show on map

Garden
Wi-Fi

Heron Suites at Port of Egypt MarineSouthold- Show on map

Very Good, 8.0

(146reviews)

Swimming pool
Wi-Fi

Avg. price/night

$233

The Pridwin HotelShelter Island Heights- Show on map

Good, 7.3

(275reviews)

Bar
Swimming pool
Babysitting
Wi-Fi

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

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

The ChequitShelter Island Heights- Show on map

Superb, 9.2

(180reviews)

Garden
24-Hour reception
Wi-Fi
Parking

Sweet Dreams Bed and Breakfast Cutchogue Cutchogue- Show on map

West Neck GuesthouseShelter Island Heights- Show on map

Superb, 9.4

(8reviews)

Room service
Garden
Wi-Fi

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

Shelter Island HouseShelter Island Heights- Show on map

Fabulous, 8.7

(25reviews)

Room service
Swimming pool
Spa
Garden
Wi-Fi

Avg. price/night

$401

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

Sunset BeachShelter Island Heights- Show on map

6.0

(133reviews)

Room service
Pet friendly
Private beach
Babysitting
Wi-Fi

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

The Inn at Harbor Knoll Greenport- Show on map

Avg. price/night

$432

Sannino Vineyard B&B Cutchogue- Show on map

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

Greenporter HotelGreenport- Show on map

Very Good, 8.0

(348reviews)

Avg. price/night

$199

The Menhaden Hotel Greenport- Show on map

24-Hour reception
Wi-Fi

Avg. price/night

$441

Greenport Captain's House Greenport- Show on map

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

Harbor Knoll Bed and BreakfastGreenport- Show on map

Swimming pool
Wi-Fi

Avg. price/night

$476

Shinn Estate Vineyards and FarmhouseMattituck- Show on map

Superb, 9.1

(227reviews)

Wi-Fi

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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