Winchester Vacations from $482

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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 $1,403, price is now $482 per person
$482
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,106, price is now $931 per person
$931
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Excellent hotel in all aspects. Comfortable and spacious rooms and attentive staff. Only exception is $70 valet parking which is way over priced (even for Boston) especially on a weekend evening.

Reviewed on Dec 7, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,929, price is now $1,093 per person
$1,093
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,231, price is now $761 per person
$761
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Everything was great

Reviewed on Dec 9, 2025

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $940, price is now $586 per person
$586
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
The rooms were clean, bathroom facilities were always clean and spotless. The gym and other amenities were great

Reviewed on Dec 10, 2025

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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

4.5/5(2,499 reviews)

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

Fenway Park
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 reviews)

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
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 reviews)

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

Harvard University

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
Museum of Ice Cream Boston

Museum of Ice Cream Boston Admission Ticket

$51
per adult
Museum of Ice Cream Boston Admission Ticket
Boston Bruins Ice Hockey Game at TD Garden

Boston Bruins Ice Hockey Game at TD Garden

$155
per adult
Boston Bruins Ice Hockey Game at TD Garden
See all activities in Winchester

Winchester Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $202 total per night from Dec 14 to Dec 15
$202 total
Dec 14 - Dec 15
Total with taxes and fees
9.6/10 Exceptional! (3,774 reviews)
Great stay! Staff was on point!

Reviewed on Dec 7, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $251 total per night from Jan 1 to Jan 2
$251 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9/10 Wonderful! (4,285 reviews)
Room was neat but too small. We did not liked that we ordered room service thinking they will bring the cart with the food in regular dishes and utensils, like in any hotel of this level, and instead they brought our food in a shopping bag on disposable containers/plastic utensils(???). There was ...

Reviewed on Dec 10, 2025

Omni Boston Hotel at the Seaport
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$119 nightly
The price is $139 total per night from Dec 15 to Dec 16
$139 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (6,039 reviews)
Clean, quiet room. Excellent location for the price. Would highly recommend!!

Reviewed on Dec 7, 2025

Harborside Inn Of Boston
See all 3,978 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.

Find the Best Winchester Vacation Packages

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 $482 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.

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