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
19 Aug - 20 Aug
Tomorrow
20 Aug - 21 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Shelter Island Heights hotels with a pool

1. 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.
฿17,693
฿22,236 total
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel

2. 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.
฿10,396
฿11,877 total
includes taxes & fees
17 Sept - 18 Sept
Shelter Island House

3. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
฿10,305
฿11,774 total
includes taxes & fees
17 Sept - 18 Sept
West Neck Guesthouse

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
฿9,148
฿12,154 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn

5. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
฿8,913
฿13,000 total
includes taxes & fees
15 Sept - 16 Sept
Sound View Greenport

6. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
฿10,779
฿13,581 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate

7. North Fork Resort

North Fork Resort
Greenport
฿10,562
฿12,067 total
includes taxes & fees
20 Sept - 21 Sept
North Fork Resort

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
฿10,075
฿14,441 total
includes taxes & fees
20 Sept - 21 Sept
Cliffside Resort Condominiums

9. 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.
฿3,325
฿3,824 total
includes taxes & fees
13 Sept - 14 Sept
Quality Inn Old Saybrook - Westbrook

10. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
฿2,616
฿3,009 total
includes taxes & fees
2 Sept - 3 Sept
Clinton Motel
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

Sound View Greenport

Sound View Greenport

8/10 Good
"Stayed here for 2 nights mid-August. Pool was nice (could have been a little cleaner). Restaurant, excellent. Valet staff, excellent. Front desk staff, good. Bar, nice. Breakfast included, very nice. Room, a bit dated but nicely renovated. Through the years I always wanted to stay here - glad I did. The view (and sunset) of the Long Island Sound from the shared balcony cannot be beat. Breathtaking."
Barbara 2-night trip
Posted 3 hours ago
Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Debra 1-night trip
Posted 9 hours ago
Water's Edge Resort & Spa
 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Theresa 4-night trip
Posted 1 day ago
Hampton's Vacation Inn
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"It was a great stay!"
Tynan 2-night trip
Posted 2 days ago
Ocean Resort Inn

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 located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Offers a seasonal outdoor pool, an indoor pool and a private beach.
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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