Winthrop Vacations

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Find the Best Winthrop Vacation Packages

Winthrop Hotel Deals

Dog Friendly Cabin Right On The Water!!!
Dog Friendly Cabin Right On The Water!!!
Winthrop
2/10 (1 review)
Be warned !
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so ..."

Reviewed on 7 July 2023

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Dog Friendly Cabin Right On The Water!!!
Escape to our cozy Winthrop cabin on Dexter Pond
Escape to our cozy Winthrop cabin on Dexter Pond
Winthrop
10/10 Exceptional! (11 reviews)
Amazing!
"Cute little cabin overlooking a beautiful view of the lake. The owners were extremely kind and easy to work with. Overall amazing experience and would stay again in a heartbeat."

Reviewed on 21 October 2024

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Escape to our cozy Winthrop cabin on Dexter Pond
Cottage on Cobbosseecontee Lake. Dates available.
Cottage on Cobbosseecontee Lake. Dates available.
Winthrop
9.8/10 Exceptional! (153 reviews)
Another great stay!!
"Second time at this location, this time to ice fish. Amazing location... cant get any closer to the lake!! All amenities are great, furniture super comfy. To incude the bed and pillows!! Will be back again this summer!!"

Reviewed on 18 March 2025

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Cottage on Cobbosseecontee Lake. Dates available.
See all 462 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.

Frequently asked questions

How much does a Winthrop vacation package cost?
Offering excellent value package deals 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?
Travel in the off-season and you’re likely to get cheap Winthrop vacation packages. Bear in mind that public holidays and major festivals and events can have an impact on prices, so do your research before booking.
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.
How to plan a trip to Winthrop?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Winthrop.
  2. Set your budget: Consider expenses like flights, food and transportation when working out how much to put aside for your trip to Winthrop. Then, choose a hotel that matches your budget, whether that’s a low-cost stay or a more upscale retreat.
  3. Decide how long to go away for: Now that you’re more familiar with Winthrop, you can figure out the ideal length of your vacation. Create a draft itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Winthrop vacation package.

Discover the most popular places to visit in Winthrop

Mt Pisgah Conservation Area Trailhead

You can take time to visit Mt Pisgah Conservation Area Trailhead during your travels to Winthrop.

Mt Pisgah Conservation Area Trailhead