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.
Atlantic Coast Inn

Atlantic Coast Inn

2 out of 5
per person
Oct 3 - Oct 6
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Augusta (AUG)
8.2/10 Very Good! (878 reviews)
Terrible daily housekeeping service, had problem with TV. Sink drain backed up. Holes in sheets. Hole in bath towel. Generally poor upkeep

Reviewed on Aug. 2, 2025

House near Acadia National Park

House near Acadia National Park

4 out of 5
per person
Oct 3 - Oct 6
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Augusta (AUG)
9.8/10 Exceptional! (18 reviews)
This house was perfect for my girls trip. Close to bar harbor and Acadia national park. The home was clean and full of everything we need for our stay. Highly recommend this house! When I return to Bar Harbor I will be staying here again!

Reviewed on Jun. 30, 2025

Stone Park

Stone Park

4 out of 5
per person
Oct 3 - Oct 6
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Augusta (AUG)
9/10 Wonderful! (97 reviews)
Very nice place to stay. Beautiful

Reviewed on Aug. 1, 2025

Hampton Inn Ellsworth/Bar Harbor

Hampton Inn Ellsworth/Bar Harbor

2.5 out of 5
per person
Oct 4 - Oct 11
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Augusta (AUG)
9.2/10 Wonderful! (1,005 reviews)
Nice hotel within drivable distance of Acadia. Plenty of shops and restaurants close by.

Reviewed on Jul. 30, 2025

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
per person
Oct 3 - Oct 6
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Augusta (AUG)
8.2/10 Very Good! (1,008 reviews)
Not enough hot breakfast choices.

Reviewed on Aug. 2, 2025

Ready to book your vacation to Winthrop?

 

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Winthrop Hotel Deals

Escape to our cozy Winthrop cabin on Dexter Pond

Escape to our cozy Winthrop cabin on Dexter Pond

Winthrop
10/10 Exceptional! (17 reviews)
"Awesome cabin on Dexter Pond! Rick and LouAnne were terrific hosts! We loved drinking coffee on porch overlooking the pond, watching sunset and kayaking. Saw family of loons and bald eagle on the large pond. Classic Maine cabin! Not big but comfortable. Hosts were very responsive if we had any questions. ..."

Reviewed on Jul. 30, 2025

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Escape to our cozy Winthrop cabin on Dexter Pond
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Winthrop
9.4/10 Exceptional! (13 reviews)
Tranquil and beautiful waterfront spot
"Well kept with all the right amenities. Beautiful views."

Reviewed on Jul. 23, 2024

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Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Aug 17 to Aug 18
CA $236
CA $257 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"The hotel is convenient to get to, and on site amenities were excellent."

Reviewed on Jul. 30, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
See all 492 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winthrop vacation package cost?
Offering excellent value package deals from CA $1,521 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.

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