Winthrop Vacations from $756
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The Latest Winthrop Vacation Packages
- Smuggler's Cove Inn
Sep 16 - Sep 20Smuggler's Cove Inn + Flight
East Boothbay4 nights2.5 star property9.0/10 - Wonderful (502 reviews)"Staff were good during check in. Easy and informative. The room was clean and spacious with a large deck and ocean view. We had complimentary buffet breakfast, which was very good with lots of food choices. The grounds and buildings could use some maintenance, due to peeling paint and overgrown landscaping. Pool area was clean with a heated pool. Onsite restaurant was limited on food choices. Otherwise this was a very good place to stay as a resort in a quiet beautiful location."Reviewed July 30, 2026Roundtrip • Chicago (CHI) - Augusta (AUG)ORD - PWM • Nonstop PWM - ORD • 1 stop$858$756found 1 day agoper traveler - Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor
Oct 13 - Oct 17Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor + Flight
Ellsworth4 nights3.0 star property8.2/10 - Very Good (1,003 reviews)"Front desk and lobby was smelly need to renovation."Reviewed July 31, 2026Roundtrip • Philadelphia (PHL) - Augusta (AUG)PHL - BGR • Nonstop BGR - PHL • Nonstop$1,135$932found 1 day agoper traveler - Topside Inn
Oct 8 - Oct 12Topside Inn + Flight
Boothbay Harbor4 nights3.0 star property10/10 - Exceptional (134 reviews)Roundtrip • Chicago (ORD) - Augusta (AUG)ORD - BGR • Nonstop BGR - ORD • Nonstop$1,560$1,289found 12 hours agoper traveler - House near Acadia National Park
Oct 15 - Oct 18House near Acadia National Park + Flight
Ellsworth3 nights4.0 star property9.6/10 - Exceptional (25 reviews)"Nice clean place, but one of the rooms was not how it was pictured. Instead of a queen, it had bunk beds. Water pressure was great upstairs but low downstairs in the bathroom. Also, ice maker didn't work. Great location"Reviewed June 25, 2026Roundtrip • Chicago (CHI) - Augusta (AUG)ORD - BHB • 1 stop BHB - ORD • 2 stops$2,353$1,989found 13 hours agoper traveler - Bluebird Ocean Point Inn
Sep 16 - Sep 20Bluebird Ocean Point Inn + Flight
Ocean Point4 nights3.0 star property8.8/10 - Excellent (596 reviews)"Aaaas"Reviewed July 30, 2026Roundtrip • Chicago (CHI) - Augusta (AUG)ORD - PWM • Nonstop PWM - ORD • 1 stop$929$789found 1 day agoper traveler
Winthrop Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
Maine Evergreen Hotel, an Ascend Collection Hotel
Best Western Plus Augusta Civic Center Inn
Best Western Plus Augusta Civic Center Inn
Homewood Suites by Hilton Augusta
Homewood Suites by Hilton Augusta
Frequently Asked Questions
How much does a Winthrop vacation package cost?
Offering excellent value package deals from $756 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?
If you're hoping to snag a cheap Winthrop vacation package, consider planning a trip in October, November and December. You're likely to find lower rates on flights and hotels during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Winthrop?
With a well-planned schedule, you can easily tick off the top Winthrop sights in a few days. But if you want to discover hidden gems or take day trips, consider booking your Winthrop vacation 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 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.
Does Expedia offer Book Now, Pay Later Winthrop vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Winthrop vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.