A pebbled beach with a sunset and a distant bridge.

Search Hotels with Pool in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Pool

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Shelter Island Heights hotels with a pool

Property amenity
Front of property – evening/night
Bar (on property)
Property amenity

1. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
Rp5.615.019
Rp6.415.237 total
includes taxes & fees
17 Aug - 18 Aug
Shelter Island House
Seasonal outdoor pool, pool umbrellas, pool loungers
Terrace/patio
Terrace/patio
Premium bedding, iron/ironing board, free WiFi, individually furnished

2. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
Rp10.008.398
Rp12.578.016 total
includes taxes & fees
8 Sept - 9 Sept
The Pridwin Hotel
Beach nearby
Property grounds
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets
Free self-parking

3. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
Rp5.566.193
Rp6.359.486 total
includes taxes & fees
17 Aug - 18 Aug
West Neck Guesthouse
Combined shower/bathtub, designer toiletries, hair dryer, towels
Restaurant
Lobby
Lobby

4. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
Rp6.027.822
Rp7.594.679 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
View from room
Suite, 1 Bedroom, Terrace, Harbour View | Frette Italian sheets, premium bedding, down duvets, pillow-top beds
Studio (Suite, King) | Frette Italian sheets, premium bedding, down duvets, pillow-top beds

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
Rp4.904.819
Rp6.516.618 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers
Desk, laptop workspace, blackout curtains, iron/ironing board
Lobby
Lobby sitting area

6. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
  • Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
Rp1.795.918
Rp2.065.306 total
includes taxes & fees
1 Sept - 2 Sept
Quality Inn Old Saybrook - Westbrook
Outdoor pool
Free daily continental breakfast
Lobby
Building design

7. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
Rp8.344.850
Rp9.533.991 total
includes taxes & fees
7 Sept - 8 Sept
Sag Harbor Inn
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Condo | 2 bedrooms, iron/ironing board, free WiFi, individually decorated
Condo | 2 bedrooms, iron/ironing board, free WiFi, individually decorated
Condo | Terrace/patio

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
Rp5.441.730
Rp7.800.127 total
includes taxes & fees
9 Sept - 10 Sept
Cliffside Resort Condominiums
Seasonal outdoor pool
Free cots/infant beds, rollaway beds, free WiFi, bed sheets
Property grounds
Free self-parking

9. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
Rp1.562.440
Rp1.796.806 total
includes taxes & fees
30 Aug - 31 Aug
Clinton Motel
Exterior
Bar (on property)
3 restaurants; breakfast, lunch, dinner and brunch served
Exterior

10. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
  • Pristine waters await at this coastal retreat with private beach access and year-round pools.
Rp4.463.380
Rp5.439.160 total
includes taxes & fees
1 Sept - 2 Sept
Water's Edge Resort & Spa
View all properties

Choose what matters most at hotels with a pool in Shelter Island Heights

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shelter Island Heights Hotel Reviews

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"a"
Heather 1-night trip
Posted 7 hours ago
The Pridwin Hotel
Aqualina Inn Montauk

Aqualina Inn Montauk

10/10 Excellent
"This place was perfect for our weekend getaway to Montauk"
Matthew 2-night trip
Posted 10 hours ago
Aqualina Inn Montauk
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"This is one of our most favorites! The rooms are amazing ( we prefer to spend a little extra for the ocean view). Dinner there is great!. The staff is exceptional."
Jen 1-night trip
Posted 20 hours ago
Water's Edge Resort & Spa
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Amazing stay& amazing staff 10/10"
Sarah 3-night trip
Posted 2 days ago
Montauk Yacht Club
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Great location, nice pool,"
Vanessa matias 3-night trip
Posted 4 days ago
The Atlantic Hotel

Frequently asked questions

What's it like visiting Shelter Island Heights?
If taking it easy by the pool is your idea of a great getaway, you may want to consider Shelter Island Heights, which offers 10 places to stay with pools. During your trip, you can explore sights such as Sunset Beach and Crescent Beach, and then relax poolside at one of the accommodation options in Shelter Island Heights that guests like for their pools.
What are some accommodation options with pools in Shelter Island Heights?
The Pridwin Hotel: Features a private beach, a seasonal outdoor pool and a full-service spa. The Chequit: Provides free self parking, a seasonal outdoor pool and complimentary bicycles. West Neck Guesthouse: Offers a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel, 1-minute walk from The Hamptons Beaches. Features a sauna, a seasonal outdoor pool and free self parking. Sound View Greenport: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
How many pool hotels will I find in Shelter Island Heights?
Expedia has 10 hotels in Shelter Island Heights for your poolside break.
What is there to see and do in Shelter Island Heights?
Spend some time experiencing the great outdoors at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Country Club, Sylvester Manor and Menhadden Lane Beach during your stay. Take in the natural beauty of Shelter Island Heights with the island views and beaches.
When is the best time to book a hotel with a pool in Shelter Island Heights?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Shelter Island Heights in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 3°C.

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