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.
Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

2.5 out of 5
Price was CA $915, price is now CA $764 per person
CA $764
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
7.8/10 Good! (1,000 reviews)
We booked a mobility handicapped room. The room was very small and my husband could not use a scooter in the room very well. The facility had an overall outdated feel but the staff tried to help the best that they could.

Reviewed on Jul 8, 2026

Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was CA $987, price is now CA $813 per person
CA $813
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.4/10 Very good! (381 reviews)
Loved the pool and natural surroundings. Staff was friendly. Our room was very dated and in need of update. Patio door difficult to operate. Television did not work, no signal. Maintenance tried to fix but I don’t think there was a fix to it. Did not like the Murphy bed setup. No headboard to sit up in bed to read, watch tv. No end tables by the bed. We just felt this was a strange setup. Overall though we enjoyed our stay.

Reviewed on Jul 5, 2026

Jordan Hotel

Jordan Hotel

3 out of 5
Price was CA $975, price is now CA $804 per person
CA $804
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (540 reviews)
Best experoence so far. We will be back again

Reviewed on Jul 6, 2026

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
Ocean Point
Price was CA $1,291, price is now CA $1,084 per person
CA $1,084
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (568 reviews)
The ocean views were perfect

Reviewed on Jul 8, 2026

Senator Inn & Spa

Senator Inn & Spa

3 out of 5
Price was CA $957, price is now CA $841 per person
CA $841
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8/10 Very good! (1,003 reviews)
The king room was huge, had a separated living room, desk & bar area. Had a TV in the bathroom for the jacuzzi tub, bathrobes in the closet, bed was very comfortable. We would have used the fireplace but we were there in June. Easy to find and a Target and a few food places in walking distance. We ordered from the restaurant for dinner and it was delicious. And reasonably priced.

Reviewed on Jul 9, 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
All Inclusive Vacations
Beach Vacations
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Family Vacations
Family Vacations

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 $764 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.