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Explore Hotels with Swimming Pools in Shelter Island Heights

The Pridwin Hotel

Shelter Island Heights, NY
9.2

Superb

104 reviews

Top rated

Pool

Parking

Free WiFi

from
$710
/ night

Shelter Island House

Shelter Island Heights, NY
9.2

Superb

58 reviews

Top rated

Pool

Parking

Free WiFi

from
$229
/ night

Sound View Greenport

Southold, NY
8

Very good

650 reviews

Relax at a beachfront hotel with a private beach, seasonal outdoor pool, and on-site dining in Southold, New York.

Top rated

Pool

Parking

Free WiFi

from
$348
/ night

The Harbor Front Inn

Greenport, NY
8.6

Fabulous

607 reviews

Enjoy a seasonal outdoor pool and complimentary breakfast near Greenport's attractions.

Top rated

Pool

Parking

Free WiFi

from
$276
/ night

The Cliffside Resort Condominiums

Greenport West, NY
9

Superb

253 reviews

Top rated

Pool

Parking

Free WiFi

from
$299
/ night

Hotel Moraine

Greenport West, NY
9.8

Exceptional

22 reviews

Top rated

Pool

Parking

Free WiFi

from
$488
/ night

Cliffside Resort Poolside Condo A204

Greenport West, NY
9.9

Exceptional

17 reviews

Top rated

Pool

Free WiFi

Air Conditioned

from
$755
/ night

Two Bed Condo with Garden Views

Greenport West, NY
10

Exceptional

4 reviews

Top rated

Pool

Free WiFi

Air Conditioned

from
$758
/ night

North Fork Resort

Greenport West, NY
9.6

Exceptional

1 review

Top rated

Pool

Parking

Free WiFi

from
$318
/ night

New Construction Greenport Pool House - 3 Blocks from Town

Greenport, NY
9.8

Exceptional

83 reviews

Top rated

Pool

Free WiFi

Refrigerator

from
$1,262
/ night

Sag Harbor Inn

Sag Harbor, NY
8.7

Fabulous

620 reviews

Enjoy a seasonal outdoor pool and complimentary breakfast near The Hamptons Beaches in Sag Harbor.

Top rated

Pool

Parking

Free WiFi

from
$357
/ night

Faraway Sag Harbor

Sag Harbor, NY
9

Superb

292 reviews

Top rated

Pool

Parking

Free WiFi

from
$971
/ night

Large Contemporary for Your Enjoyment

Noyack, NY
8.8

Fabulous

17 reviews

Top rated

Pool

Free WiFi

Air Conditioned

from
$2,205
/ night

Cowgirl Palace

Sag Harbor, NY

5-star

Pool

Parking

Free WiFi

from
$442
/ night

Hamptons 9BD MEGA Compound w POOL TENNIS BBALL NIGHTCLUB

Sag Harbor, NY

Pool

Parking

Free WiFi

Free Parking

from
$3,446
/ night

Beautiful Sag Harbor Home with Pool and easy walk to private beach or downtown

Sag Harbor, NY

Pool

Free WiFi

Sauna

Refrigerator

from
$1,248
/ night

East Hampton Art House Bed and Breakfast

Springs, NY
9.6

Exceptional

65 reviews

Top rated

Pool

Parking

Free WiFi

from
$908
/ night

The Sagaponack

Wainscott, NY
8.8

Fabulous

257 reviews

Enjoy a seasonal outdoor pool and free Wi-Fi at this comfortable hotel near The Hamptons Beaches.

Top rated

Pool

Parking

Free WiFi

from
$351
/ night

EHP Resort & Marina

Springs, NY
7.4

Good

9 reviews

Pool

Parking

Free WiFi

Free Parking

from
$749
/ night

Hamptons Elegant and Comfortable Apartment

Bridgehampton, NY
9.9

Exceptional

81 reviews

Top rated

Pool

Free WiFi

Air Conditioned

from
$709
/ night

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