Winthrop Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Winthrop Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
Coolidge Corner
฿54,183
per person
4 Nov - 10 Nov
found 1 day ago
Return direct flight included
Bangkok (BKK) to Boston (BOS)
8.2/10 Very good! (4,438 reviews)
Absolutely amazing stay!
Perfect location.
Great friendly welcome at Check-in from Alberto.
Loved our room. Amazing view.
Breakfast was perfect - Ramona was so lovely and helpful.
Great to see happy smiley staff!
Would stay here again in a heartbeat!
Reviewed on 19 Sept 2026
Top hotels in Winthrop
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
฿10,564
฿13,658 total
20 Sept - 21 Sept
includes taxes & fees
9.2/10 Wonderful! (4,807 reviews)
"Great location! Room was ready early and quick uber to the game! Great bars. Beautiful view from the room."
Reviewed on 19 Sept 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
฿8,952
฿11,560 total
20 Sept - 21 Sept
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
฿4,768
฿5,553 total
20 Sept - 21 Sept
includes taxes & fees
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.
Stay near popular Winthrop attractions
Photo by The Curious Zephyr
Winthrop Beach
8.4/10 (26 reviews)
This tranquil stretch of shoreline offers panoramic views of Boston's skyline across the Atlantic. Stroll the promenade at sunrise when the soft sand and gentle waves create a perfect coastal escape.
Photo by The Curious Zephyr
Winthrop Shore Reservation
7.6/10 (5 reviews)
This Atlantic coastal retreat offers a mix of sandy and pebbly shores with stunning Boston skyline views. Enjoy morning walks along the promenade when the beach is serene and the sea breeze most refreshing.
Point Shirley Beach
8.0/10 (7 reviews)
Why not spend a lazy afternoon at Point Shirley Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.
Donovan Beach
7.6/10 (4 reviews)
This intimate sandy spot offers stunning Boston skyline views and a unique vantage point for watching planes from Logan Airport. Bring a picnic to enjoy while aircraft soar dramatically overhead.
What to do in Winthrop
Boston Old Town Trolley Hop-on Hop-Off City Tour
฿1,612
per adult
90% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
฿2,332
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
฿1,515
per adult
80% of travellers recommend
Frequently asked questions
How much does a Winthrop holiday package cost?
You can grab a holiday package to this top destination from ฿54,183 on Expedia. However, how much your holiday to Winthrop costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Winthrop?
To score cheap Winthrop holiday packages, organise your getaway outside of peak periods like public holidays and major events. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Winthrop?
Generally, a handful of days is great for a Winthrop holiday. With a well-organised schedule, you can see all the leading attractions including Winthrop Shore Reservation, as well as discover some hidden treasures along the way.
Is it worth booking a holiday package to Winthrop?
It's no wonder a Winthrop holiday is on the must-do list of many travellers. Top attractions like Winthrop Beach are just the start of things to keep you busy here.
How to find the best Winthrop package deals?
Start your search for a Winthrop package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winthrop package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winthrop escape off to a flying start.
Is it cheaper to book a Winthrop holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Winthrop escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Winthrop?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Winthrop getaway.
How to plan a trip to Winthrop?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Winthrop.
- Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodation will probably be the biggest expense during your trip to Winthrop.
- Decide your trip length: Consider how long you'd like to spend discovering Winthrop. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Combine your airfare and accommodation: After you've nailed down your trip dates and duration, book the ideal Winthrop holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
