Sag Harbor Vacation Packages

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Your Sag Harbor Vacation

Say farewell to planning hassles and hello to a Sag Harbor vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Village of Southampton, which is great for history, coastal beaches and culture. Wolffer Estates Vineyard, Sag Harbor Marine Park and LongHouse Reserve are just a few of the sights you'll want to explore during your trip to Sag Harbor. Don't delay exploring this city any longer. The perfect Sag Harbor vacation is just a few clicks away with Expedia.

Top Sag Harbor Vacation Deals

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

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,842, price is now CA $1,178 per person
CA $1,178
per person
Sep 3 - Sep 7
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Flights delayed by weather caused us to lose arranged-for transportation. Hotel staff made alternate arrangements for us to get from airport to hotel 8 hours after originally-scheduled arrival.

Reviewed on Jul 1, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,162, price is now CA $2,615 per person
CA $2,615
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Nicely designed hotel with beautiful views. Staff was very nice but service was generally slow.

Reviewed on Jun 28, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,423, price is now CA $1,533 per person
CA $1,533
per person
Sep 3 - Sep 7
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
The hotel is the heart of Times Square. The breakfast was fine. Due to heavy rush during holiday season.

Reviewed on Jun 30, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $3,055, price is now CA $1,935 per person
CA $1,935
per person
Aug 3 - Aug 8
found 7 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
We usually stay at the Ritz but prices were up overall due to the World Cup so we tried this property. It was fantastic and we may have found a new favorite.

Reviewed on Jun 15, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,445, price is now CA $1,549 per person
CA $1,549
per person
Sep 3 - Sep 7
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,099 reviews)
Excellent service snd breakfast

Reviewed on Jun 30, 2026

Sag Harbor Beach Vacation

Listen to the sound of waves breaking onto the shore and look out over the sparkling waters during your Sag Harbor vacation. If you're in need of some time out, a trip to Sag Harbor will do wonders. We have plenty of Sag Harbor packages to choose from. Lock in one near Havens Beach, just 3 kilometres from the downtown area, and live out your vacation fantasies without hurting your budget.

Ready to book your vacation to Sag Harbor?

 

Choose your dates

Sag Harbor Hotel Deals

Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
The price is CA $666 per night from Jul 13 to Jul 14
CA $666
CA $761 total
Jul 13 - Jul 14
includes taxes & fees
9.4/10 Exceptional! (640 reviews)
"Great location on the water and super walkable to everything in Sag Harbor on Main Street! We really enjoyed our time here and loved sipping our morning coffee on our balcony looking out at the water."

Reviewed on Jul 1, 2026

Sag Harbor Inn
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is CA $1,581 per night from Jul 15 to Jul 16
CA $1,581
CA $2,168 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very good! (816 reviews)
"Great experience."

Reviewed on Jun 25, 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is CA $771 per night from Jul 20 to Jul 21
CA $771
CA $1,043 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (146 reviews)
"Amazing location to the beach and town. Brand new. All the appliances and amenities were great. The pool area great as well. Currently building a bar/ resturaunt at the pool to be open for next summer Wouldn’t stay anywhere else in Montauk"

Reviewed on Jun 30, 2026

Offshore Montauk
See all 4,671 properties in Sag Harbor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
Family Vacations

Stay near popular Sag Harbor attractions

A harbor with several sailing ships and a mountainous landscape in the background.

Sag Harbor Marine Park

8.8/10 (20 reviews)
Sag Harbor Marine Park is just one of the places to see in Sag Harbor, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the beautiful beaches.
See properties

What to do in Sag Harbor

great fun with friends

Full Day Private Long Island Wine Tours from New York City

CA $262
per adult
Full Day Private Long Island Wine Tours from New York City
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

CA $1,798
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,798
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Sag Harbor

Frequently asked questions

How much does a Sag Harbour vacation package cost?
Offering great value package deals from CA $1,178 on Expedia, you'll be pleasantly surprised at how much a vacation to Sag Harbour costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Sag Harbour?
Plan your trip for the off-peak season and you're likely to get cheap Sag Harbour vacation packages. Bear in mind that public holidays and local events and festivals can impact prices, so do some research before booking.
How many days is enough for Sag Harbour?
Allow around 2 days for your Sag Harbour vacation to discover everything that makes this destination special. Explore key neighbourhoods, including East Hampton North and Wainscott Woods. Then head to the top attractions such as Elizabeth A. Morton National Wildlife Refuge and Three Mile Harbour. With a good itinerary, you can keep busy with room for some me-time too. Want to venture beyond Sag Harbour? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Sag Harbour?
Whether you'd like to check out key attractions such as Bay Street Theatre and Mashashimuet Park on your Sag Harbour vacation, or coming for its great views, culture and history, there's something for everyone here. With so many things to do, you'll soon find out why so many families think Sag Harbour is a good vacation destination.
How to find the best Sag Harbour package deals?
Use Expedia's filters to help you find some great Sag Harbour package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Sag Harbour package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Sag Harbour vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a tailored Sag Harbour vacation by choosing your favourite accommodation type, airline and car class.
How to plan a trip to Sag Harbour?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Sag Harbour.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will likely be the biggest expense during your trip to Sag Harbour.
  3. Decide how long to go away for: Now that you're more familiar with Sag Harbour, you can work out the right length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Sag Harbour vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.