Winthrop Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Mid-Town Motel
CA $836
per person
Oct 9 - Oct 12
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.6/10 Excellent! (268 reviews)
The staff was great! Very convient location. The room did the job. It was very small & twin size beds (which we knew going into it). There was some wear and tear in the room and didn’t necessarily FEEL clean. Bathroom was small. Would stay here again for convenience and right price
Reviewed on Aug 28, 2026
Spruce Point Inn
CA $1,444
per person
Oct 9 - Oct 12
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.8/10 Excellent! (431 reviews)
Spruce Point offers a classic olde Maine Down East experience. Somewhat dated facilities, but charming, well-maintained and clean. Quiet. Spectacular views of Booth Bay. Lovely well-maintained mature plantings and gardens. The ocean-side pool and hot tub areas are special! The service staff were all are polite, personable and pleasantly professional.
Reviewed on Aug 28, 2026
Comfort Inn Ellsworth - Bar Harbor
CA $1,448
per person
Oct 16 - Oct 19
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
9.2/10 Wonderful! (1,047 reviews)
The room was comfortable and clean. I was not able to get into the breakfast area most mornings. There were children running all over and touching the food.
Reviewed on Aug 28, 2026
Greenleaf Inn
CA $1,542
per person
Oct 9 - Oct 12
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
9.6/10 Exceptional! (32 reviews)
We can’t say enough about host “Jersey” and the community he has created at this lovely spot. Rooms, amenities and views are fantastic, but he goes beyond with custom tour itineraries, property tours and nightly campfires with s’mores and music. His welcoming and humorous charisma makes you feel like you are staying with an old friend!
Reviewed on Aug 25, 2026
Ready to book your vacation to Winthrop?
Winthrop Hotel Deals
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Winthrop ME
Discover your retreat - 3-bedroom cottage in Winthrop
Winthrop ME
10/10 Exceptional! (190 reviews)
"always a great place to stay."
Reviewed on Aug 24, 2026
Escape to our cozy Winthrop cabin on Dexter Pond
Winthrop ME
10/10 Exceptional! (36 reviews)
"Overall it was a fantastic stay! The hosts were great and very responsive to anything I needed. The access to the lake is a little challenging but it is also very doable for the little ones. Plenty of frogs and fish were caught. And an added bonus is, you get to sit on the porch and watch the busy ..."
Reviewed on Aug 23, 2026
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.
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.
Mt Pisgah Conservation Area Trailhead
You can take time to visit Mt Pisgah Conservation Area Trailhead during your travels to Winthrop.
Frequently asked questions
How much does a Winthrop vacation package cost?
Offering excellent value package deals from CA $836 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?
- Pick your travel dates: What you plan to do in Winthrop and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
