Winchester Vacations from $327

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Your Winchester Vacation

Book a Winchester vacation package that includes everything you need and nothing you don't. Great for nightlife, shopping and bars and pubs, consider staying in the neighborhood of Downtown Boston. A trip to Winchester is a terrific opportunity to see the sights. Be sure to look around renowned attractions like Harvard Square, Harvard University and Bentley College. Stop dreaming and start traveling. Browse the broad range of options on Expedia today and finally put your Winchester vacation plans into gear!

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
The Charles Hotel
Hyatt Place Boston/Medford
Beacon Hill Hotel
Boston Harbor Hotel
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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
$274 nightly
The price is $319 total per night from Oct 30 to Oct 31
$319 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (4,093 reviews)
"Everything was immaculate"

Reviewed on Oct 4, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$264 nightly
The price is $307 total per night from Nov 2 to Nov 3
$307 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (3,858 reviews)
"Hotel was amazing"

Reviewed on Oct 2, 2025

citizenM Boston North Station
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
$279 nightly
The price is $325 total per night from Oct 31 to Nov 1
$325 total
Oct 31 - Nov 1
Total with taxes and fees
9.4/10 Exceptional! (6,529 reviews)
"Hip and happening hotel. Financial district is a nice place. Coffee bar and restaurant in the lobby are great."

Reviewed on Oct 2, 2025

The Dagny 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.

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
21,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $327 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 vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're looking to snag a cheap Winchester vacation package, consider planning a trip in November, December and January. You'll usually find lower prices on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Winchester?
With a well-organized itinerary, you can easily tick off the main Winchester attractions in a handful of days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Winchester vacation for longer.
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 vacation as a package?
Expedia vacation 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 personalized Winchester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Winchester break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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