Winchester Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Save up to ฿4,531 when you book a flight and hotel together*
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Top hotels in Winchester

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 ฿6,807 per night from 10 Aug to 11 Aug
฿6,807
฿9,240 total
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (3,687 reviews)
"We really loved our stay. The hotel was great including the restaurants and the location can’t be beat. Seaport is an awesome area."

Reviewed on 21 Jul 2025

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 ฿5,608 per night from 27 Jul to 28 Jul
฿5,608
฿6,530 total
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (1,455 reviews)
"Very small."

Reviewed on 19 Jul 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,608 per night from 27 Jul to 28 Jul
฿5,608
฿6,531 total
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (3,565 reviews)
"Fun for 2 people who like unique things"

Reviewed on 21 Jul 2025

citizenM Boston North Station
See all 3,763 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.

Popular places to visit

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

Fenway Park

4.5/5(61 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(102 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 which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(204 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

What to do in Winchester

Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

฿1,766
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

฿1,103
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
BEST New York City Day Tour from Boston

New York City Day Tour from Boston

฿5,677
per traveller
100% of travellers recommend
New York City Day Tour from Boston
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday 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 holiday 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 holiday 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 holiday. 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 holiday as a package?
Expedia holiday 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 personalised Winchester holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 favourite 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 accommodation: After you've nailed down your travel dates and duration, lock in the right Winchester 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.