Winthrop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, 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.

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 Jul. 7, 2023

Get rates
Dog Friendly Cabin Right On The Water!!!
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! (12 reviews)
Autumnal Joy
"I just wrote an extensive review to VACASA. Please see that!!"

Reviewed on Oct. 9, 2023

Get rates
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Cottage on Cobbosseecontee Lake. Dates available.
Cottage on Cobbosseecontee Lake. Dates available.
Winthrop
9.8/10 Exceptional! (143 reviews)
Lake life on Cobossee
"Had an awesome time staying at Kara’s house on Lake Cobbosseecontee in Winthrop. She was an excellent host and the property is amazing. Absolutely are looking forward to going back next year. Thanks again"

Reviewed on Jun. 16, 2024

Get rates
Cottage on Cobbosseecontee Lake. Dates available.
See all 449 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?
Less than you might think — from only , in fact! By bundling flights, hotels and car rentals into your own custom-built vacation package, your trip to Winthrop is just a few clicks away.
How do I get a cheap travel package to Winthrop?
Combine your flights and hotels, toss in extras such as a rental car or activities, and save with a Winthrop vacation package. You won’t just score impressive discounts on your getaway — you’ll have loads of choice too. When you book through Expedia, you’ll have your pick of over 550 air carriers and 1,000,000 properties around the globe. Your dream vacation begins right here, right now!
Where should I stay in Winthrop?
Stay close to the action. Many people like to book hotels around top attractions, like Maranacook Lake, Annabessacook Lake and Mt Pisgah Conservation Area Trailhead.
What are the top hotels in Winthrop?
If this will be your first visit to Winthrop, book a room at Walk To Townbeach Or Kayak From Backyard To Lake Annabessacook. Walk Downtown or Life On The Lake With Private Dock And Fire Pit. Both offer comfortable beds and are top options with lots of travelers.
How far in advance should I book my Winthrop vacation?
It can be hard to know when is the ideal time to book your Winthrop trip. But typically the earlier you book, the better the prices. Sometimes, you can book your flights and hotels up to 12 months prior to departure. If you’re eager to escape on a last-minute getaway, no need to worry! There are incredible bargains popping up on Expedia every single day.
What does an Expedia Winthrop travel package include?
Hotels, rental cars and flights — you’ll find them all here. With Expedia, you can shape your Winthrop package the way you like it. All you have to do is work out just what you need. Once you’ve made your booking, you can add extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Winthrop travel package?
Bundling your bookings into a Winthrop vacation package is the easiest way to organize your trip. Not only that, you’ll save just for combining your hotels, flights and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Winthrop Expedia vacation package?
Yes, and with over 550 airlines to choose from throughout the world, you have loads of choice. Have a look through the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Winthrop vacation package?
You can. We understand that life doesn’t always go to plan, so we’re happy to help if you have to make changes to your Winthrop vacation package. It may be possible to cancel or amend your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Winthrop

Image for Mt Pisgah Conservation Area Trailhead

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