Water Mill Vacation Packages 2026 from $277

Water Mill flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Liberty Inn

$277

per person

Jun 18 - Jun 20

found 1 day ago

Roundtrip flight included

Washington (IAD) to New Haven (HVN)

Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.

Head of Pond House

Save 100% on your flight

$1,333

per person

Jun 18 - Jun 20

found 1 day ago

Roundtrip flight included

Washington (IAD) to New Haven (HVN)

A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a communal living room are also on offer.

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

$294

per person

Jun 18 - Jun 20

found 1 day ago

Roundtrip flight included

Washington (IAD) to New Haven (HVN)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.

Home2 Suites by Hilton East Haven New Haven

The Centre

$379

per person

Jun 18 - Jun 20

found 1 day ago

Roundtrip flight included

Washington (IAD) to New Haven (HVN)

This inn features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

The Scranton Seahorse Inn

Madison Center

$476

per person

Jun 18 - Jun 20

found 1 day ago

Roundtrip flight included

Washington (IAD) to New Haven (HVN)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Free full breakfast is served. A terrace, a garden, and a lobby fireplace are also on offer.

Top Water Mill hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$593 nightly

$677 total

May 19 - May 20

Total with taxes and fees

This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

On private beach

Pool

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$193 total

May 21 - May 22

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's a garden and multilingual staff can provide around-the-clock assistance.

Pool

Pet friendly

Sound View Greenport

58775 County Rd 48 Greenport NY

$370 nightly

$422 total

May 19 - May 20

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.

On private beach

Pool

Sag Harbor Inn

45 West Water Street Sag Harbor NY

$315 nightly

$360 total

May 25 - May 26

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. Enjoy the free continental breakfast each morning. A fireplace in the lobby and luggage storage are also provided.

Pool

Breakfast included

The Harbor Front Inn

209 Front St Greenport NY

$292 nightly

$334 total

May 19 - May 20

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental breakfast each morning.

Pool

Breakfast included

The Shoals Suites and Slips

61600 Main Rd Southold NY

$267 nightly

$302 total

May 19 - May 20

Total with taxes and fees

This hotel features a bar/lounge, a coffee shop, and a communal living room. A business center, a picnic area, and express check-out are also on offer.

Free WiFi

Air conditioning

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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.

Popular places to visit

Parrish Art Museum

5/5(4 reviews)

Browse the contemporary artwork displays, discover the talents of some the Hamptons best known artists and admire the barn-like design of this Long Island legend.

Duck Walk Vineyards

Sample award-winning wines and take some bottles home as souvenirs when you visit one of two beautiful vineyards that have become Long Island institutions.

Atlantic Golf Course

Enjoy a round of golf in Water Mill at Atlantic Golf Course. While you're in the area, stroll along the beautiful beaches.

Frequently asked questions

How much are vacation packages to Water Mill?

Prepare to be pleasantly surprised — you could find yourself in Water Mill for as little as $277. Here at Travelocity, we save you money and stress with our awesome vacation package deals. With flights, hotels and experiences all in one place, why put it off?

How long should my Water Mill vacation be?

Around 4 nights is the average amount of time travelers vacation in Water Mill. But the ideal trip length comes down to how many cherished memories you want to create. Why not allow a few extra days and discover some of the lesser-known spots?

Where can I get the best vacation package deals for Water Mill?

For the perfect package deal to Water Mill, head straight to Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties worldwide to create the ideal escape — the choice is all yours!

Why should I purchase my Water Mill vacation package via Travelocity?

By booking your hotel, flights, activities and car rental all in the one place, you'll save big bucks as well as precious time. We have an expert team of customer service specialists available 24/7, and you'll know that you'll always score the best deal in town with our Price Match Guarantee. So, what are you waiting for? Book your dream getaway today and start packing!

Will I save money on my Water Mill car rental if I combine it with my hotel or flight?

With a Water Mill vacation package, you can bundle your flight, hotel and car bookings and save a whole lot. When you're ready to see the best of this impressive region, why not make a beeline for Times Square? This must-see sight is 85 mi from Water Mill. With a rental car, you'll be there in the blink of an eye.

Which airport is best for Water Mill?

MacArthur Airport (ISP) (40 mi away from the city center), Tweed - New Haven Regional Airport (HVN) (35 mi away from central Water Mill) and Hartford, CT (HFD-Hartford - Brainard) (60 mi away from central Water Mill) are the best options for Water Mill.

What is there to do in Water Mill?

There is a certain kind of magic as you stroll the streets of Water Mill. Duck Walk Vineyards and Atlantic Golf Course are just two landmarks that make this city so special, so put them at the top of your to-do list.

Where should I stay when visiting Water Mill?

Many visitors opt to check in to the 1940s Fisherman's Cottage close to beach. Right next to the Water Mill museum.. It's a great base for your Water Mill getaway.