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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

CA $1,067
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Great stay!

Reviewed on Aug 28, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $2,762
per person
Oct 7 - Oct 11
found 2 days ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Seven Beach Lane

Seven Beach Lane

CA $1,571
per person
Oct 4 - Oct 10
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (33 reviews)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
CA $5,482
per person
Nov 1 - Nov 8
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (695 reviews)
Lovable

Reviewed on Aug 26, 2026

Eurostars Wall Street

Eurostars Wall Street

Manhattan
CA $1,296
per person
Oct 5 - Oct 9
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,014 reviews)
Everything was fine, the Breakfast was great.

Reviewed on Aug 25, 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.

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Sag Harbor Hotel Deals

Faraway Sag Harbor

Faraway Sag Harbor

31 West Water Street Sag Harbor NY
CA $926
CA $1,164 total
Sep 10 - Sep 11
includes taxes & fees
Faraway Sag Harbor
Sag Harbor Inn

Sag Harbor Inn

45 West Water Street Sag Harbor NY
CA $492
CA $562 total
Sep 20 - Sep 21
includes taxes & fees
9.4/10 Exceptional! (662 reviews)
"Location and scenery"

Reviewed on Aug 28, 2026

Sag Harbor Inn
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundable
CA $126
CA $145 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,002 reviews)
"My room smelled like urine and the lobby smelled like a wet dog. Bathroom was dim and dingy, ironing board stained, A/C vents were full of dust and didn’t work well. TV didn’t work either. How they can charge $150 for a room here is appalling. The front sign is the only thing nice about the property- ..."

Reviewed on Aug 28, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,635 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.
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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.
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A bird perched on a hand holding seeds.
Photo by M L

Elizabeth A. Morton National Wildlife Refuge

7.4/10 (6 reviews)
Explore the great outdoors at Elizabeth A. Morton National Wildlife Refuge, a lovely green space in Noyack. While you're in the area, stroll along the beautiful beaches.
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Noyac Golf Club

6.4/10 (5 reviews)
Enjoy a round of golf in Noyack at Noyac Golf Club. While you're in the area, stroll along the beautiful beaches.
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Havens Beach

8.4/10 (14 reviews)
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.
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Bay Street Theatre

8.4/10 (15 reviews)
You can get tickets for a performance at Bay Street Theatre during your trip to Sag Harbor. While you're in the area, stroll along the beautiful beaches.
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Sag Harbor Whaling and Historical Museum

6.0/10 (3 reviews)
You can spend time studying the exhibits at Sag Harbor Whaling and Historical Museum in Sag Harbor. While you're in the area, stroll along the beautiful beaches.
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Mashashimuet Park

Mashashimuet 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.
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Off the Rocker

10.0/10 (1 review)
Enjoy an outing to Off the Rocker during your stay in Sag Harbor. While you're in the area, stroll along the beautiful beaches.
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What to do in Sag Harbor

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

CA $242
per adult
Sunday Brunch Sail in Greenport
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
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,797
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 $1,067 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.

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