A wooden gazebo by a pond with a large tree trunk nearby.

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Check availability on Shelter Island Hotels with a Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (260 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
The price is AED 2,000
AED 3,019 total
includes taxes & fees
22 Jul - 23 Jul
Marram
Aerial view

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (287 reviews)
  • cleanliness
    Pristine white sand meets heated pool paradise just steps from your suite.
The price is AED 1,815
AED 2,346 total
includes taxes & fees
22 Jul - 23 Jul
The Surf Club
Indoor pool, 2 outdoor pools

Montauk Yacht Club

Montauk Yacht Club
4.5 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Dive into waterfront luxury with private beach and 2 outdoor pools, perfect for a refreshing Hamptons retreat with marina views.
The price is AED 2,612
AED 3,403 total
includes taxes & fees
3 Aug - 4 Aug
Montauk Yacht Club
Indoor spa tub

Montauk Blue Hotel

Montauk Blue Hotel
2.0 star property
Downtown Montauk
9.2 out of 10, Wonderful, (247 reviews)
  • cleanliness
    Dive into seaside bliss with Montauk Blue Hotel's indoor pool and hot tub, just steps from sandy shores.
The price is AED 1,931
AED 2,385 total
includes taxes & fees
26 Jul - 27 Jul
Montauk Blue Hotel
Exterior

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (320 reviews)
  • cleanliness
    Coastal retreat with outdoor pool and free bicycles for exploring Montauk's beaches and scenic trails.
The price is AED 1,570
AED 1,794 total
includes taxes & fees
2 Aug - 3 Aug
Daunt's Albatross Motel
Terrace/patio

A Wave Inn

A Wave Inn
2.5 star property
Downtown Montauk
7.6 out of 10, Good, (136 reviews)
  • cleanliness
    Splash into Hamptons vibes at a seasonal pool oasis near Montauk Point beaches.
The price is AED 1,199
AED 1,657 total
includes taxes & fees
22 Jul - 23 Jul
A Wave Inn
Seasonal outdoor pool, sun loungers

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (522 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is AED 1,451
AED 1,658 total
includes taxes & fees
29 Jul - 30 Jul
Ocean Resort Inn
Seasonal outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas

Ocean Surf Resort

Ocean Surf Resort
2.0 star property
Downtown Montauk
8.4 out of 10, Very Good, (275 reviews)
  • cleanliness
    Seasonal Montauk retreat with sun-drenched pool deck offering ocean views, just steps from downtown.
The price is AED 1,612
AED 2,002 total
includes taxes & fees
26 Jul - 27 Jul
Ocean Surf Resort
Seasonal outdoor pool, sun loungers

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (532 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is AED 1,084
AED 1,238 total
includes taxes & fees
29 Jul - 30 Jul
Aqualina Inn Montauk
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 3,560
AED 4,487 total
includes taxes & fees
28 Jul - 29 Jul
Offshore Spa & Residences
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The setting, the staff, the luxurious bath, the balcony…all exceptional"
Daria 1-night trip
Posted less than an hour ago
Saybrook Point Resort & Marina

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Frequently asked questions

What are some accommodations with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor pools, a children's pool, and a private beach. Montauk Yacht Club: Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking.
What is there to see and do in Shelter Island?
Explore places like The Hamptons Beaches while you're in the area. Make a point to visit attractions like Sunset Beach and Shelter Island Whale's Tail.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be what you want if you come to town during the coldest months of January, February, or March when the average temperature is 38°F.