Winchester Holidays

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Your Winchester Holiday

Lock in a Winchester holiday package that has everything you need and no unnecessary extras. Great for nightlife, shopping and bars and pubs, consider staying in the neighbourhood of Downtown Boston. You'll want to sightsee during your trip to Winchester. Drop by leading attractions such as Harvard Square, Harvard University and Bentley College. Expedia is here to help you escape your daily routine. Tailor your holiday to Winchester to match your travel style, whatever that may be.

Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
21,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Museum of Science

Our pick of the best Winchester Hotel Deals

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 AU$266 per night from 30 Mar to 31 Mar
AU$266
includes taxes & fees
30 Mar - 31 Mar
9.4/10 Exceptional! (898 reviews)
"Property is super convenient to lots of great activities. Local eateries nearby. Transportation a breeze. And the best part of my stay: the friendly helpful staff and the refreshing spring aroma of a spotless room upon arrival."

Reviewed on 26 Mar. 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is AU$533 per night from 29 Mar to 30 Mar
AU$533
includes taxes & fees
29 Mar - 30 Mar
9.4/10 Exceptional! (2,858 reviews)
"A convenient and affordable option in the Seaport, friendly and helpful staff."

Reviewed on 24 Mar. 2025

Seaport Hotel Boston
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is AU$275 per night from 30 Mar to 31 Mar
AU$275
includes taxes & fees
30 Mar - 31 Mar
9/10 Wonderful! (4,739 reviews)
"The hotel is in the perfect location. Close to so many activities as well as food/bars. It's also close to the harbor in the event you want to take a ferry to another town. We loved it!"

Reviewed on 25 Mar. 2025

Harborside Inn Of Boston
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.

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.

Discover the most popular places to visit in Winchester

What to do in Winchester

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