Winthrop Vacations from $540
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The Latest Winthrop Vacation Packages
- Bluebird Ocean Point Inn
Sep 24 - Sep 27Bluebird Ocean Point Inn + Flight
Ocean Point3 nights3.0 star property8.8/10 - Excellent (585 reviews)"The resort grounds were beautiful and located in a peaceful setting. We were pleasantly surprised by the restaurant and bar which were very convenient after being out all day exploring. The only issue we found was the King room was smaller than expected and if you’re put in one of the rooms in the house, the main door doesn’t have a damper on it so it would slam shut every time someone came and went which was very jarring."Reviewed July 21, 2026Roundtrip • Philadelphia (PHL) - Augusta (AUG)PHL - BOS • Nonstop BOS - TTN • 1 stop$661$540found 22 hours agoper traveler - Topside Inn
Sep 24 - Sep 27Topside Inn + Flight
Boothbay Harbor3 nights3.0 star property10/10 - Exceptional (128 reviews)Roundtrip • Philadelphia (PHL) - Augusta (AUG)PHL - BOS • Nonstop BOS - TTN • 1 stop - Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor
Sep 3 - Sep 7Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor + Flight
Ellsworth4 nights3.0 star property8.2/10 - Very Good (1,000 reviews)"We didn't have anything from the kitchen. The front desk person, Lauren was on duty when we actually checked in. We had to wait 20 minutes for her to answer the phone several times, then stay on another call to help someone plan a trip 2 weeks from now. I actually said "put her in hold" so 3 of us waiting in line could get into our pre-booked room. Obviously needs some training. Plus we asked for a certain room on the first floor at booking and it was not scheduled. We have back issues and had..."Reviewed July 21, 2026Roundtrip • Denver (DEN) - Augusta (AUG)DEN - BGR • 1 stop BGR - DEN • 1 stop$1,198$1,000found 1 day agoper traveler - Mid-Town Motel
Oct 2 - Oct 5Mid-Town Motel + Flight
Boothbay Harbor3 nights2.0 star property8.6/10 - Excellent (248 reviews)"Very clean room. Extremely pleasant and helpful staff. Very convenient to walk into town. Excellent air conditioning since we stayed in 80+ outside temperatures."Reviewed July 21, 2026Roundtrip • Minneapolis (MSP) - Augusta (AUG)MSP - BOS • 1 stop BOS - MSP • 1 stop$760$651found 5 hours agoper traveler - OneSixtyFive
Sep 3 - Sep 7OneSixtyFive + Flight
Brunswick4 nights3.0 star property9.4/10 - Exceptional (160 reviews)"This is a perfect and cozy getaway in the heart of Brunswick. Everything is within walking distance. Quiet and tucked away."Reviewed July 17, 2026Roundtrip • Denver (DEN) - Augusta (AUG)DEN - BGR • 1 stop BGR - DEN • 1 stop$1,416$1,215found 1 day agoper traveler
Winthrop Hotel Deals
Best Western Plus Augusta Civic Center Inn
Best Western Plus Augusta Civic Center Inn
Maine Evergreen Hotel, an Ascend Collection Hotel
Maine Evergreen Hotel, an Ascend Collection HotelFrequently Asked Questions
How much does a Winthrop vacation package cost?
Offering excellent value package deals from $540 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.