Winchester Holidays

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Winchester Holiday

Our pick of the best 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 NZ$483 per night from 10 Aug to 11 Aug
NZ$483
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (3,695 reviews)
"Room was spacious and clean. The restaurants in the hotel were great, a little costly but delicious food."

Reviewed on 16 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 NZ$341 per night from 27 July to 28 July
NZ$341
27 July - 28 July
includes taxes & fees
9.2/10 Wonderful! (1,438 reviews)
"loved staying here. there is plenty of space to relax and make time pass by while you explore boston. the rooms were clean and chic. would recommend to a friend :)"

Reviewed on 16 Jul. 2025

citizenM Boston Back Bay
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
9/10 Wonderful! (5,339 reviews)
"Would highly recommend. The staff was very friendly and helpful. The location was great. The room was very clean, comfortable, and quiet. Will definitely stay here again."

Reviewed on 17 Jul. 2025

Get rates
Harborside Inn Of Boston
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.

Discover the most popular places to visit in Winchester

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

Fenway Park

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.

Harvard University
Gillette Stadium

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's great live music and acclaimed theatre scene.

Gillette Stadium

What to do in Winchester

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$132
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

NZ$91
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

NZ$57
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.