Winchester Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Boston Harbor Hotel
The Langham, Boston
Raffles Boston
Encore Boston Harbor

Top hotels in Winchester

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 €216 per night from 16 Feb to 17 Feb
€216
includes taxes & fees
16 Feb - 17 Feb
9.6/10 Exceptional! (2,750 reviews)
"Night club and kids friendly"

Reviewed on 30 Jan 2025

Seaport Hotel Boston
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €164 per night from 23 Feb to 24 Feb
€164
includes taxes & fees
23 Feb - 24 Feb
8.2/10 Very Good! (3,289 reviews)
"Beautiful Lobby. Had an excellent Old Fashioned"

Reviewed on 27 Jan 2025

Hilton Boston Park Plaza
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is €122 per night from 2 Feb to 3 Feb
€122
includes taxes & fees
2 Feb - 3 Feb
9/10 Wonderful! (4,620 reviews)
"Wonderful service, welcoming, very cool hotel super conveniently located next to Faneuil Hall. Close to highways and parking garage conveniently around the corner."

Reviewed on 28 Jan 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 from €2,039 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.

Popular places to visit

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.