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.
2 bedroom luxury Empire State VIEW
Manhattan
Price was CA $5,507, price is now CA $2,421 per person
CA $2,421
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was CA $2,142, price is now CA $1,272 per person
CA $1,272
per person
Aug 13 - Aug 16
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,593 reviews)
Great location, comfortable bed, and a nice-sized room. Overall, the stay was enjoyable. I booked a Felix room but received a regular-sized room, which was a little disappointing.
The check-in lines were very long, and the elevators were often crowded due to the number of guests. The bed was large and comfortable, but there weren’t enough pillows provided for the size of the bed.
A good hotel with a convenient location, but a few areas could use improvement
Reviewed on Jun 19, 2026
Hotel Riu Plaza New York Times Square
Manhattan
Price was CA $1,909, price is now CA $1,188 per person
CA $1,188
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,063 reviews)
Good location, big breakfast buffet that was decent, loved happy hour at the bar. The hall way to the room seemed a little dirty or musty to us and the room was pretty decent but the shower drain seemed clogged as it drained slowly and it was kinda awkward taking a shower because the toilet and shower is surrounded by frosted glass and when your showering everyone in the room gets a shadow show of you showering. I guess that’s ok for couples but if you are there with a family or friends then it is different level. lol but all in all we enjoyed it and we would stay again
Reviewed on Jun 17, 2026
1 Hotel Brooklyn Bridge
Price was CA $4,662, price is now CA $2,901 per person
CA $2,901
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.
Reviewed on Jun 6, 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.
Sag Harbor Hotel Deals
Sag Harbor Inn
45 West Water Street Sag Harbor NY
The price is CA $663 per night from Jul 19 to Jul 20
CA $663
CA $757 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (630 reviews)
"The hotel is great. Very well located and the room is very spacious and comfortable."
Reviewed on Jun 17, 2026
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is CA $1,363 per night from Jul 1 to Jul 2
CA $1,363
CA $1,868 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (802 reviews)
"Our room was not what we thought we reserved. I was told that because we reserved online, there was a mix up and that next time we should call the resort directly. The on the beach cottage was what we wanted. The room we got was located high above the beach and in order to access the beach we had ..."
Reviewed on Jun 17, 2026
Offshore Montauk
71 S Emerson Ave Montauk NY
The price is CA $871 per night from Jul 5 to Jul 6
CA $871
CA $1,157 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (140 reviews)
"Positives, Great location and a nice hotel, nice pool, steps to the beach with beach chairs and umbrella service right on the beach.with very helpful and friendly staff. Nice bathroom with a great shower, fluffy towels and good toiletries. On the downside, the room itself was tiny, no room to move ..."
Reviewed on Jun 18, 2026
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.
Discover the most popular places to visit in Sag Harbor
Havens Beach
If a restful vacation is part of your travel plans, Havens Beach might be the perfect place to seek out during your trip to Sag Harbor. While you're in the area, stroll along the waterfront.
What to do in Sag Harbor
Full Day Private Long Island Wine Tours from New York City
CA $262
per adult
Hamptons Private Day Trip from New York City
CA $1,798
per traveller
The Hamptons and Long Island Wineries Private Tour
CA $1,798
per traveller
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- Flights to Hamptons
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- Bedell Cellars
- Visit Bridgehampton
- Castello di Borghese / Hargrave Vineyard
- Cooper's Beach
- East Hampton Main Beach
- East Hampton Vacations
- First United Methodist Church
- Georgica Beach
- Hampton Bays Vacations
- Hamptons Vacations
- Visit Hamptons
- Havens Beach
- Hither Hills State Park
- Hither Woods Preserve
- Kontokosta Winery
- Longhouse Reserve
- Martha Clara Vineyards
- Montauk Vacations
- Napeague State Park
- Visit North Haven
- North Main Street Historic District
- Old Hook Mill
- Orient Vacations
- Parrish Art Museum
- Pindar Vineyards
- Pollock-Krasner House and Study Center
- Ponquogue Beach
- Visit Bay Point
- Shadmoor State Park
- Shelter Island Heights Vacations
- Shinnecock Nation Cultural Center and Museum
- Southampton Arts Center
- Southampton Vacations
- Visit Wainscott Woods
- Wolffer Estates Vineyard
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
