Find Hotels with a Pool in Sag Harbor, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sag Harbor Hotels with a Pool

Our top choices for Sag Harbor hotels with a pool

Outdoor pool

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (614 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
The price is ￥50,107
￥57,249 total
includes taxes & fees
Jun 2 - Jun 3
Sag Harbor Inn
Exterior

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
  • cleanliness
    Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
The price is ￥119,123
￥149,709 total
includes taxes & fees
Jun 10 - Jun 11
Faraway Sag Harbor
Interior

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
  • cleanliness
    Unwind in the outdoor pool with bayfront views, or soak in a hot tub at this private Sag Harbor retreat with dock access.
The price is ￥715,815
￥1,013,007 total
includes taxes & fees
May 27 - May 28
Sag Harbor Water View w Dock 1.5ml from town
Pool

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is ￥635,320
￥1,035,248 total
includes taxes & fees
May 24 - May 25
Spacious 5-bedroom house with water views and 2 houses from the bay.
Seasonal outdoor pool, sun loungers

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is ￥23,065
￥26,351 total
includes taxes & fees
May 25 - May 26
Ocean Resort Inn
Seasonal outdoor pool, sun loungers

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (497 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is ￥19,884
￥22,719 total
includes taxes & fees
May 21 - May 22
Aqualina Inn Montauk
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (189 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
The price is ￥15,290
￥22,653 total
includes taxes & fees
May 21 - May 22
Breakers Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (892 reviews)
  • cleanliness
    Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.
The price is ￥23,446
￥27,857 total
includes taxes & fees
Jun 14 - Jun 15
Kenny's Tipperary Inn
Outdoor pool, pool umbrellas, sun loungers

Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
The price is ￥40,098
￥63,986 total
includes taxes & fees
May 25 - May 26
Offshore Montauk
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (500 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is ￥31,655
￥40,143 total
includes taxes & fees
May 25 - May 26
The Bentley Hotel Southampton
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.
View all properties

Choose what matters most at hotels with a pool in Sag Harbor

Breakfast included
4 stars

Top Sag Harbor Hotel Reviews

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Great view!"
Nicki 1-night trip
Posted 9 hours ago
Montauk Yacht Club

Frequently asked questions

What's it like visiting Sag Harbor?
If taking it easy by the pool is your idea of a great getaway, you might want to think about Sag Harbor, which has 5 places to stay with pools. During your trip, you can explore attractions like Bay Street Theatre and Havens Beach, and then relax and unwind poolside at one of the accommodations in Sag Harbor that guests like for their pools.
What are some hotels with pools in Sag Harbor?
Sag Harbor Inn: Hotel, 1-minute walk from The Hamptons Beaches. Features daily, a seasonal outdoor pool, and free self parking. Gurney's Montauk Resort & Seawater Spa: Vacation home, 6-minute walk from The Hamptons Beaches. Offers sun loungers, a pool, and complimentary wireless internet access. Montauk Manor: Resort, 13-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Aparthotel, 14-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children's pool, and a private beach.
How many pool hotels will I be able to find in Sag Harbor?
Expedia has 5 hotels in Sag Harbor for your poolside break.
What is there to see and do in Sag Harbor?
Surround yourself with nature at The Hamptons Beaches and Havens Beach. During your stay, check out sights such as Bay Street Theatre, Foster Memorial Town Beach, and Noyac Golf Club.
When is the best time to book a hotel with a pool in Sag Harbor?
You may want to consider a place to stay that has an outdoor pool if you're planning to visit Sag Harbor in the hottest months of August, July, or September when the average temperature is 70°F. Lodging with 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 38°F.