A sunset over a coastal landscape with grasses and a distant shoreline.

Sagaponack Vacations from $289

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Your Sagaponack Vacation

Say goodbye to the stress of planning and hello to a Sagaponack vacation package. With the finer details organized before you leave, you can focus on discovering this city, starting with Village of Southampton, which is great for history, coastal beaches and culture. Make your trip to Sagaponack even more fun by going sightseeing. Wolffer Estates Vineyard, Sag Harbor Marine Park and Parrish Art Museum are among the major attractions worth exploring. A couple of quick clicks is all it takes to create a customized Sagaponack vacation on Expedia.

The Latest Sagaponack Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 11 - Dec 13

    Pier Blue Inn Old Saybrook - Essex + Flight

    Saybrook Manor
    2 nights
    2.0 star property
    8.0/10 - Very good (1,008 reviews)
    Roundtrip • San Juan (SJU) - New Haven (HVN)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $346
    $289
    per traveler
    found 1 day ago
    Pier Blue Inn Old Saybrook - Essex
  • Jan 17 - Jan 19

    Beechmont - Perfect for Family Retreat! + Flight

    North End
    2 nights
    5.0 star property
    Roundtrip • Tampa (TPA) - New Haven (HVN)
    TPA - LGA • Nonstop LGA - TPA • Nonstop
    Save 100% on your flight
    $1,568
    $868
    per traveler
    found 1 day ago
    Beechmont - Perfect for Family Retreat!
  • Dec 18 - Dec 21

    Landing Apartments New Haven Near Dixwell + Flight

    Newhallville
    3 nights
    3.0 star property
    2.0/10 - (1 review)
    "The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host."
    Reviewed May 25, 2026
    Roundtrip • Raleigh (RDU) - New Haven (HVN)
    RDU - HVN • Nonstop HVN - RDU • Nonstop
    $668
    $554
    per traveler
    found 10 hours ago
    Landing Apartments New Haven Near Dixwell
  • Dec 18 - Dec 21

    Landing Apartments Downtown New Haven + Flight

    Downtown New Haven
    3 nights
    3.0 star property
    Roundtrip • Raleigh (RDU) - New Haven (HVN)
    RDU - HVN • Nonstop HVN - RDU • Nonstop
    $633
    $530
    per traveler
    found 10 hours ago
    Landing Apartments Downtown New Haven
  • Dec 18 - Dec 21

    Luxury Residences Downtown New Haven + Flight

    The Hill
    3 nights
    4.0 star property
    9.2/10 - Wonderful (36 reviews)
    "Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again."
    Reviewed October 25, 2026
    Roundtrip • Raleigh (RDU) - New Haven (HVN)
    RDU - HVN • Nonstop HVN - RDU • Nonstop
    $760
    $656
    per traveler
    found 10 hours ago
    Luxury Residences Downtown New Haven

Discover the most popular places to visit in Sagaponack

What to do in Sagaponack

Sagaponack Hotel Deals

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.

Frequently Asked Questions

How much does a Sagaponack vacation package cost?

You can pick up a vacation package to this top destination from $289 on Expedia. However, how much your vacation to Sagaponack costs will depend on the season, hotel choice and length of stay.

What are the cheapest months to go to Sagaponack?

You can usually find lower rates and greater availability in January, October and December. Take a look at our cheap Sagaponack vacation packages and you could land some great off-season deals.

How many days is enough for Sagaponack?

With a well-organized travel plan, you can easily tick off the main Sagaponack attractions in a few days. But if you'd like to discover hidden gems or take day trips, consider booking your Sagaponack vacation for longer.

How to find the best Sagaponack package deals?

Finding a cheap Sagaponack package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Sagaponack package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.

Is it cheaper to book a Sagaponack vacation as a package?

You can enjoy significant savings on your Sagaponack retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Sagaponack?

If you're considering a spontaneous Sagaponack adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.

How to plan a trip to Sagaponack?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Sagaponack.
  2. Set a budget: Factor in costs such as flights, meals and transportation when working out how much to put aside for your trip to Sagaponack. Then, pick a hotel that fits your budget, whether that's a low-cost option or a more luxurious getaway.
  3. Explore Sagaponack using our trip planning tool: Gain insights into the top attractions and best properties for your trip to Sagaponack. You can also save your favorite places, collaborate with your group and manage your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Sagaponack, you can figure out the ideal length of your vacation. Put together a draft itinerary and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Sagaponack vacation package.
  6. Add on experiences and excursions: Take a look at our travel guide to find some awesome things to do in Sagaponack. Book tickets or make reservations before you go to save time and avoid the stress of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Sagaponack vacation packages?

If you're anything like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Sagaponack break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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