Winthrop Holidays

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    Better together
    Save up to HK$1,282 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Winthrop

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Winthrop
Tranquil and beautiful waterfront spot
"Well kept with all the right amenities. Beautiful views."

Reviewed on 23 Jul 2024

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Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Escape to our cozy Winthrop cabin on Dexter Pond
Escape to our cozy Winthrop cabin on Dexter Pond
Winthrop
10/10 Exceptional! (12 reviews)
So relaxing!
"The cabin was so clean and welcoming. Our hosts were friendly and helpful. The views of the pond were wonderful. We were looking for a peaceful get away and it was just that! Will go back next year."

Reviewed on 30 Jun 2025

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Escape to our cozy Winthrop cabin on Dexter Pond
Located directly in central downtown and beach area, fish or kayak from backyard
Located directly in central downtown and beach area, fish or kayak from backyard
Winthrop
Lake Region Charmer
"We stayed at this home while in town for Maine 70.3. The location was great. Winthrop is a cute little town. Home was close to two beautiful lakes. The backyard was very peaceful, right next to a stream. The home was well appointed and had everything we needed. The communication with the host was ..."

Reviewed on 4 Aug 2024

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Located directly in central downtown and beach area, fish or kayak from backyard
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.

Frequently asked questions

How much does a Winthrop holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Winthrop costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Winthrop?
Travel in the off-season and you're likely to get cheap Winthrop holiday 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 many days is enough for Winthrop?
With a well-organised itinerary, you can easily hit the most popular Winthrop attractions in a handful of days. But if you want to discover lesser-known spots or go on day tours, consider booking your Winthrop holiday for longer.
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 holiday package well in advance.
Is it cheaper to book a Winthrop holiday as a package?
You can enjoy significant savings on your next Winthrop getaway by booking a customised holiday 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 holiday 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 holiday. 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 personalised Winthrop holiday package.

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