The Best Hotels with a Pool in Sag Harbor, NY from ￥14,509 in 2026

Q: 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 : Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor : Aparthotel, 14-minute walk from The Hamptons Beaches. Provides 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. Sound View Greenport : Offers a private beach, a seasonal outdoor pool, and 2 bars.

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Our top choices for Sag Harbor hotels with a pool

Sag Harbor Inn

Sag Harbor

Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.

￥45,647 total

includes taxes & fees

May 12 - May 13

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

Sag Harbor

￥1,010,854 total

includes taxes & fees

May 15 - May 16

Sag Harbor Water View w Dock 1.5ml from town

Bay Point

Unwind in the outdoor pool with bayfront views, or soak in a hot tub at this private Sag Harbor retreat with dock access.

￥1,001,724 total

includes taxes & fees

May 18 - May 19

Ocean Resort Inn

Downtown Montauk

Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.

￥22,377 total

includes taxes & fees

May 13 - May 14

Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.

￥14,509 total

includes taxes & fees

May 17 - May 18

The Penny Lane

Hampton Bays

Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.

￥50,784 total

includes taxes & fees

May 26 - May 27

Seasonal outdoor pool, pool umbrellas, sun loungers

Kenny's Tipperary Inn

Culloden Shores

Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.

￥23,528 total

includes taxes & fees

May 18 - May 19

Aqualina Inn Montauk

Downtown Montauk

Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.

￥22,377 total

includes taxes & fees

May 13 - May 14

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

Breakfast included

4 stars

Top Sag Harbor Hotel Reviews

Sound View Greenport

4/10 Poor

"They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty."

Hyatt Place Long Island East End

10/10 Excellent

"The breakfast was delicious, the rooms were nice, and the bar was perfect. In all of my travels I think the staff at this hotel might be the nicest, most accommodating people I’ve ever met. They truly made our stay wonderful. Olga and the other front desk staff were amazing. "

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: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides 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. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars.

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 Havens Beach and The Hamptons Beaches. During your stay, check out sights such as Noyac Golf Club, Bay Street Theatre, and Foster Memorial Town Beach.

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.

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