Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ana Lei

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 6.057.671 ₫ per night from 19 Jul to 20 Jul
6.057.671 ₫
8.122.112 ₫ total
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (3,626 reviews)
"We really enjoyed our stay at the Omni. They were accommodating with everything, even allowing us to check-in hours earlier than expected. It is a bit of a walk to get to the waterfront but we didn’t mind! The rooftop pool and hot tub area were really nice with a bar right beside. The artist rooms ..."

Reviewed on 1 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 4.552.536 ₫ per night from 6 Jul to 7 Jul
4.552.536 ₫
5.301.429 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,355 reviews)
Will Stay Here Again
"Fantastic staff and location. We will definitely be back."

Reviewed on 3 Jul 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is 6.104.833 ₫ per night from 13 Jul to 14 Jul
6.104.833 ₫
7.240.084 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9.6/10 Exceptional! (3,014 reviews)
"Highly recommend"

Reviewed on 3 Jul 2025

Seaport Hotel Boston
See all 3,740 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

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Harvard University
Copley Square

Copley Square

You can learn about the local history of Boston during your trip to a well-known site such as Copley Square. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Copley Square

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.