A wooden signpost with 'WINTHROP' written on it, surrounded by greenery and trees.

Winthrop Vacations from $283

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Your Winthrop Vacation

With all the details organized before you head off, our Winthrop vacation packages mean you can focus more on having a great time. Whether you're staying in the neighborhood of Readfield, which is good for culture, or someplace else in town, this city offers a wealth of discoveries. Fill your days with tours of Cobbosseecontee Lake, Augusta Country Club and Maranacook Lake, some of the top attractions you really should see during your trip to Winthrop. A couple of quick clicks is all it takes to create a tailored Winthrop vacation on Expedia.

The Latest Winthrop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A room with a large window, a sofa with patterned cushions, a small table with a vase of flowers, and a radiator.
    Dec 11 - Dec 13

    Evergreen Valley Inn by Coolvacay + Flight

    Stoneham
    2 nights
    3.0 star property
    8.0/10 - Very good (211 reviews)
    Roundtrip • Orlando (MCO) - Augusta (AUG)
    MCO - BOS • 1 stop PSM - MCO • 1 stop
    $339
    $283
    per traveler
    found 1 day ago
    Evergreen Valley Inn by Coolvacay
  • Balcony view
    Dec 11 - Dec 13

    Admirals Quarters Inn + Flight

    Boothbay Harbor
    2 nights
    2.0 star property
    9.4/10 - Exceptional (46 reviews)
    Roundtrip • Orlando (MCO) - Augusta (AUG)
    MCO - BOS • Nonstop PSM - MCO • 1 stop
    $433
    $403
    per traveler
    found 1 day ago
    Admirals Quarters Inn
  • An outdoor patio with seating, a fire feature, and string lights.
    Dec 18 - Dec 21

    The Brunswick Hotel + Flight

    Brunswick
    3 nights
    3.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    Roundtrip • Atlanta (ATL) - Augusta (AUG)
    ATL - BOS • Nonstop BOS - ATL • 1 stop
    $505
    $473
    per traveler
    found 8 hours ago
    The Brunswick Hotel
  • A wooden cabin with a circular entrance, a bench, and a small table.
    Dec 11 - Dec 13

    Wolf Cove Inn + Flight

    Poland
    2 nights
    4.0 star property
    10/10 - Exceptional (2 reviews)
    "Beautiful setting. Corner room with lake sunset views. Nice property for strolling and lounging in Adirondack chairs overlooking the water. Nice breakfast and restaurant with a well equipped bar."
    Reviewed October 19, 2026
    Roundtrip • Orlando (MCO) - Augusta (AUG)
    MCO - BOS • 1 stop PSM - MCO • 1 stop
    $455
    $429
    per traveler
    found 1 day ago
    Wolf Cove Inn
  • A porch with white rocking chairs, a hanging flower basket, and a sign reading 'One Sixty Five.'
    Dec 11 - Dec 13

    OneSixtyFive + Flight

    Brunswick
    2 nights
    3.0 star property
    9.4/10 - Exceptional (176 reviews)
    Roundtrip • Orlando (MCO) - Augusta (AUG)
    MCO - BOS • 1 stop PSM - MCO • 1 stop
    $366
    $349
    per traveler
    found 1 day ago
    OneSixtyFive

Where to stay near Winthrop

Discover the charm of Winthrop, Maine, where outdoor adventures and scenic beauty await. Explore the best of Winthrop’s districts and local hotspots, ideal for romance and family fun. Use an online map to uncover hidden gems in this picturesque New England town.
A historic building with a dome and scaffolding, surrounded by autumn trees.

Augusta

Discover Augusta, a charming city perfect for travelers seeking culture and outdoor adventures. With attractions like the historic Maine State House, the Augusta Civic Center for events, and nearby scenic lakes and beaches, there's something for everyone. Whether you're interested in family-friendly activities or a romantic getaway, Augusta offers a diverse experience year-round. Located about 10 miles by car from Winthrop, it's an ideal choice for your stay, ensuring you enjoy the best of Maine's capital.

North Monmouth

Experience the charm of North Monmouth, an excellent hub for family-oriented travelers eager to explore the natural beauty of Maine. With its stunning Cobbosseecontee Lake, historic lighthouse, and recreational parks, North Monmouth offers a delightful escape for those seeking outdoor adventures and scenic views. Located about 3 miles by car from Winthrop, this quaint city is a smart choice for your stay, providing easy access to nearby attractions while maintaining a cozy, budget-friendly atmosphere.

Monmouth

Make your vacation planning effortless by staying in Monmouth, a haven for nature lovers and families due to its stunning landscapes and outdoor activities. Enjoy the beauty of Cobbosseecontee Lake, explore the scenic Maple Ridge Island, or take in a show at the local theater. Just about 5 miles by car from Winthrop, Monmouth offers a peaceful retreat, making it an ideal choice for a memorable getaway.

A calm lake surrounded by rocky shores and dense forest.

Wayne

Ideally situated for adventure seekers and families, Wayne offers a perfect escape into nature, just about 5 miles by car from Winthrop. Visitors can enjoy the scenic beauty of Androscoggin Lake, unwind at the Town Beach, or explore the nearby national state park. With its peak season from June to August, Wayne provides a refreshing retreat for those looking to immerse themselves in outdoor activities and picturesque landscapes. Choosing Wayne for your stay ensures a unique experience in a charming setting.

A person wakeboarding on a wave.

Manchester

Travelers seeking a weekend getaway will find Manchester, Maine, to be the ideal base for their vacation, featuring stunning scenery and outdoor activities. With nearby attractions like the Augusta Civic Center and the historic Maine State House, visitors can enjoy cultural experiences alongside family-friendly options such as local lakes and beaches. Located about 6 miles by car from Winthrop, Manchester offers easy access to golf courses and ski fields, making it a smart choice for your stay.

Discover the most popular places to visit in Winthrop

Little Cobbossee Lake

Commune with nature and explore the great outdoors at Little Cobbossee Lake during your travels in Winthrop.
See properties

Winthrop Hotel Deals

A hotel room with a bed, a desk, a television, a painting, and a lamp.

Days Inn by Wyndham Augusta

Days Inn by Wyndham Augusta
2.0 star property
8 mi from Winthrop
6.2 out of 10, (1,000 reviews)
$89 nightly
The price is $97
Nov 8 - Nov 9
Total with taxes and fees
Days Inn by Wyndham Augusta
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.
See all properties in Winthrop

Frequently Asked Questions

How much does a Winthrop vacation package cost?

Offering excellent value package deals from $283 on Expedia, you'll be surprised at how little a vacation to Winthrop costs! Our packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Winthrop?

If you're hoping to snag a cheap Winthrop vacation package, consider planning a trip in October, November and December. You're likely to find lower rates on flights and hotels during these quieter months — perfect for budget-conscious travelers.

How many days is enough for Winthrop?

With a well-planned schedule, you can easily tick off the top Winthrop sights in a few days. But if you want to discover hidden gems or take day trips, consider booking your Winthrop vacation for longer.

How to find the best Winthrop package deals?

Use Expedia's handy filters to help you find some unbeatable Winthrop package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Winthrop package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.

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

You can enjoy significant savings on your next Winthrop getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Winthrop?

If you're considering a spontaneous Winthrop adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.

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

If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Winthrop vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure 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.