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

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $824, price is now $327 per person
$327
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,244, price is now $737 per person
$737
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
Excellent restaurant options within walking distance

Reviewed on Oct 5, 2025

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

3 out of 5
Save 100% on your flight
Price was $720, price is now $452 per person
$452
per person
Dec 7 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,449 reviews)
The water was off when we checked in at midnight. The room was dusty and the bathroom walls had water damage the wallpaper was bubbled with water!

Reviewed on Oct 4, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,116, price is now $709 per person
$709
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (246 reviews)
Lean room, nice staff but the elevator broke and it took a while to fix it

Reviewed on Oct 1, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,353, price is now $867 per person
$867
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Easy access to mass transit and to all the downtown areas of interest.

Reviewed on Oct 4, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winchester
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Discover the most popular places to visit in Winchester

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

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Winchester

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

$49
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

$28
per adult
LEGO Discovery Center Boston Admission Ticket
See all activities in Winchester

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
See all 3,769 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.

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.