Winchester Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Save up to NT$5,067 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NT$6,947 per night from Aug 7 to Aug 8
NT$6,947
NT$9,273 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (3,651 reviews)
"We just had a wonderful stay at the Omni seaport ! It was July 4th weekend so it was. Busy but still the hotel was very attentive and organized . From valet to front desk , to the pool staff everyone was friendly and helpful and also had in room dining for breakfast from kestra ans it was amazing ..."

Reviewed on 2025/7/8

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NT$5,344 per night from Jul 20 to Jul 21
NT$5,344
NT$6,223 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,373 reviews)
"First time there. Wanted something walkable to Fenway Park. Definitely unique. I had a smaller room. It was fine for me, but didn’t like the bed totally against the wall. Wish it had makings for simple coffee in am instead of going downstairs. Would have liked a hot tub too. But I would go back"

Reviewed on 2025/7/6

citizenM Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NT$4,525 per night from Jul 20 to Jul 21
NT$4,525
NT$5,269 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (3,718 reviews)
"The Room was a decent size, and the staff was very kind and helpful."

Reviewed on 2025/7/7

Copley Square Hotel, a FOUND Hotel
See all 3,748 properties in Winchester
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.

Discover the most popular places to visit in Winchester

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices on Expedia for your Winchester break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
Plan your trip for the shoulder or low season and you're likely to find cheap Winchester vacation packages. Keep in mind that public holidays and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Winchester?
Usually, a handful of days is enough to check out the major attractions during your Winchester vacation. But if you'd like to have some time to rest or take day tours, think about extending your trip.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Winchester package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester adventure off to a flying start.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Winchester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Winchester?
Score incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Winchester getaway.
How to plan a trip to Winchester?

  1. Choose your travel dates: The things you'd like to do in Winchester and your favorite season will help you decide when to go.
  2. Set your budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Winchester. Then, pick a hotel that works with your budget, whether that's an affordable option or a more luxurious retreat.
  3. Decide how many days away: Start by listing all the attractions you want to experience in Winchester. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Winchester vacation package for you.

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