Winthrop Vacations from ￥332,136

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winthrop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cambridge Common House

Cambridge Common House

4 out of 5
West Cambridge
Price was ￥419,702, price is now ￥332,136 per person
￥332,136
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
10/10 Exceptional! (17 reviews)
What an absolutely beautiful hotel, filled with lovely, tasteful touches, and an incredibly kind and attentive staff. I can’t wait to go back and stay again!

Reviewed on Jul 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥717,511, price is now ￥475,932 per person
￥475,932
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Great location and very helpful staff

Reviewed on Jul 16, 2026

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was ￥446,540, price is now ￥343,348 per person
￥343,348
per person
Sep 5 - Sep 10
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,011 reviews)
The Charles Hotel exceeded expectations on every front. The rooms and common areas were spotless, and the amenities felt genuinely upscale. Staff were accommodating and allowed us extra time to check out, which made the end of our stay stress-free. On-site parking was a huge plus, and the location couldn’t be better — just steps from Harvard Square, with great restaurants and shops within easy walking distance. Highly recommend for anyone visiting the area.

Reviewed on Jul 17, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was ￥516,161, price is now ￥401,416 per person
￥401,416
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,273 reviews)
Fantastic stay. Beautiful property and location. Lots of amazing places to eat nearby

Reviewed on Jul 19, 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Price was ￥486,332, price is now ￥384,246 per person
￥384,246
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (5,113 reviews)
Small room with a broken TV. Clean but not a great value.

Reviewed on Jul 19, 2026

Find the Best Winthrop Vacation Packages

Winthrop Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is ￥38,846 per night from Jul 31 to Aug 1
￥38,846
￥51,855 total
Jul 31 - Aug 1
includes taxes & fees
Omni Boston Hotel at the Seaport
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is ￥26,164 per night from Aug 16 to Aug 17
￥26,164
￥35,191 total
Aug 16 - Aug 17
includes taxes & fees
Hyatt Regency Boston/Cambridge
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥23,269 per night from Aug 16 to Aug 17
￥23,269
￥27,097 total
Aug 16 - Aug 17
includes taxes & fees
The Revolution Hotel
See all 4,224 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.

Stay near popular Winthrop attractions

A lighthouse with a red, white, and blue top, a beach, and a town with houses.
Photo by The Curious Zephyr
Open 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.
See properties

What to do in Winthrop

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,526
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

￥7,680
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥13,653
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities in Winthrop

Frequently asked questions

How much does a Winthrop vacation package cost?
You can grab a vacation package to this top destination from ￥332,136 on Expedia. However, how much your vacation 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 vacation packages, organize 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 vacation. With a well-organized 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 vacation package to Winthrop?
It's no wonder a Winthrop vacation is on the must-do list of many travelers. 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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize 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 vacation 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?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Winthrop.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Winthrop.
  3. 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.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Winthrop vacation package for you.

Explore a world of travel with Expedia

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