Winthrop Vacation Packages

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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.

Top Winthrop Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Topside Inn

Topside Inn

3 out of 5
Price was CA $2,006, price is now CA $1,557 per person
CA $1,557
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
10/10 Exceptional! (113 reviews)
First, the location. What a beautiful view. Next, the room was so nicely renovated. The modern amenities with old world charm. The bathroom was so liluxorious. Next the breakfast was superb. And the extra touches like unlimited drinks and water, freshly baked cookies. Definitely coming back next year.

Reviewed on Jul 12, 2026

House near Acadia National Park

House near Acadia National Park

4 out of 5
Price was CA $5,025, price is now CA $4,038 per person
CA $4,038
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
9.6/10 Exceptional! (25 reviews)
Nice clean place, but one of the rooms was not how it was pictured. Instead of a queen, it had bunk beds. Water pressure was great upstairs but low downstairs in the bathroom. Also, ice maker didn't work. Great location

Reviewed on Jun 25, 2026

Spruce Point Inn

Spruce Point Inn

3.5 out of 5
Price was CA $1,982, price is now CA $1,660 per person
CA $1,660
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (411 reviews)
Great

Reviewed on Jul 13, 2026

Newly Renovated Acadia Apartment Maple Street

Newly Renovated Acadia Apartment Maple Street

3 out of 5
Price was CA $3,213, price is now CA $2,764 per person
CA $2,764
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
10/10 Exceptional! (3 reviews)
Entry door was confusing.

Reviewed on Jul 1, 2026

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Winthrop Hotel Deals

Enjoy Sunset views on tranquil Dexter Pond

Enjoy Sunset views on tranquil Dexter Pond

Winthrop ME
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Enjoy Sunset views on tranquil Dexter Pond
Escape to our cozy Winthrop cabin on Dexter Pond

Escape to our cozy Winthrop cabin on Dexter Pond

Winthrop ME
10/10 Exceptional! (28 reviews)
"Randy and I were looking for a peaceful getaway on the water, and Dexter Pond was exactly what we were hoping for.The cabin was spacious, clean, and comfortable, with beautiful views of the pond from the front porch. We really enjoyed relaxing there and taking in the scenery.Randy had a great time ..."

Reviewed on Jun 25, 2026

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Escape to our cozy Winthrop cabin on Dexter Pond
Discover your retreat - 3-bedroom cottage in Winthrop

Discover your retreat - 3-bedroom cottage in Winthrop

Winthrop ME
10/10 Exceptional! (185 reviews)
"this cabin is great, big yard, plenty of parking, and a great dock for mooring a boat.The cabin is extremely clean, check in is a breeze and there is a Hannafords, large hardware store and gas 10 minutes away. I will be back for sure."

Reviewed on Jun 18, 2026

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Discover your retreat - 3-bedroom cottage in Winthrop
See all 533 properties in Winthrop
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
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Stay near popular Winthrop attractions

Little Cobbossee Lake

Commune with nature and explore the great outdoors at Little Cobbossee Lake during your travels in Winthrop.
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Frequently asked questions

How much does a Winthrop vacation package cost?
Offering excellent value package deals from CA $1,557 on Expedia, you'll be thrilled with how little a vacation to Winthrop costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winthrop?
To pick up cheap Winthrop vacation packages, organize your getaway outside of busy periods such as public holidays. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Winthrop?
You can easily explore all the top attractions in Winthrop in a few days, including the popular Annabessacook Lake. If you're after a longer Winthrop vacation, look at what kind of day trips and activities are available close by.
How to find the best Winthrop package deals?
Use Expedia's filter tool to help you find some unbeatable Winthrop package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winthrop package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Winthrop vacation as a package?
You can enjoy significant savings on your next Winthrop getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winthrop?
Land amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Winthrop getaway.
How to plan a trip to Winthrop?

  1. Pick your travel dates: What you plan to do in Winthrop and your favourite season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to airfares and activities. Your hotel will likely be the largest expense during your trip to Winthrop.
  3. Work out your trip length: Think about how long you want to spend exploring Winthrop. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Winthrop 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.