Discover Shelter Island Heights Hotels with Flexible Cancellation Options

9.2

Superb

104 reviews

Top rated

Pool

Parking

Free WiFi

from

$710

/ night

West Neck Guesthouse

8

Good

37 reviews

Parking

Free WiFi

Free Parking

Family Room

from

$249

/ night

Shelter Island House

9.2

Superb

58 reviews

Top rated

Pool

Parking

Free WiFi

from

$229

/ night

The Chequit

9

Superb

2 reviews

Top rated

Garden

from

$627

/ night

American Beech Hotel

8.9

Fabulous

222 reviews

Top rated

Free WiFi

Spa & wellness services

Non-Smoking Rooms

from

$379

/ 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

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

9

Superb

253 reviews

Top rated

Pool

Parking

Free WiFi

from

$299

/ night

The Menhaden Hotel

9.5

Exceptional

183 reviews

Top rated

Parking

Free WiFi

Free Parking

from

$524

/ night

The Shoals Suites & Slips

Southold, NY

9.3

Superb

274 reviews

Experience luxury with individually decorated rooms, outdoor spaces, and a coffee shop at this Southold hotel near the bay.

Top rated

Parking

Free WiFi

Free Parking

from

$331

/ night

Newly Renovated 2-BR Apartment

10

Exceptional

80 reviews

Top rated

Free WiFi

Air Conditioned

Kitchen/kitchenette

from

$610

/ night

Hotel Moraine

9.8

Exceptional

22 reviews

Top rated

Pool

Parking

Free WiFi

from

$488

/ night

Cliffside Resort Poolside Condo A204

9.9

Exceptional

17 reviews

Top rated

Pool

Free WiFi

Air Conditioned

from

$755

/ night

ZEY HOTEL

8.1

Very good

4 reviews

Top rated

Parking

Free WiFi

Free Parking

from

$276

/ night

Two Bed Condo with Garden Views

10

Exceptional

4 reviews

Top rated

Pool

Free WiFi

Air Conditioned

from

$758

/ night

North Fork Resort

9.6

Exceptional

1 review

Top rated

Pool

Parking

Free WiFi

from

$318

/ night

American Beech - Deluxe King 5

Spa & wellness services

Refrigerator

TV

Coffee / Tea Maker

from

$367

/ night

American Beech in Greenport - Deluxe King Suite 11

Spa & wellness services

Refrigerator

TV

Coffee / Tea Maker

from

$397

/ night

American Beech in Greenport - Two-Bedroom Apartment 8

Spa & wellness services

Refrigerator

TV

Coffee / Tea Maker

from

$512

/ night

Oyster Estate