Winchester Vacations from $382

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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.
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

3 out of 5
Spring Hill
Price was $617, price is now $382 per person
$382
per person
Feb 5 - Feb 10
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Not a ton around the hotel, but easily walkable to things. Very safe and quit area. The hot cocoa in the evening was a nice touch! We did have issues with the hot water running out, but managed. Overall a fabulous experience and stay.

Reviewed on Jan 4, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,352, price is now $454 per person
$454
per person
Feb 5 - Feb 10
found 21 hours 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

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $1,815, price is now $895 per person
$895
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Price was $637, price is now $399 per person
$399
per person
Feb 5 - Feb 10
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
Nice views, and I love that everything in the room can be controlled by the iPad.

Reviewed on Jan 3, 2026

The Atlas Hotel

The Atlas Hotel

3.5 out of 5
Allston
Price was $3,014, price is now $1,902 per person
$1,902
per person
Feb 5 - Feb 10
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
No reviews
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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
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
TD Garden

TD Garden

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden

What to do in Winchester

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
92% 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

$35
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Museum of Ice Cream Boston

Museum of Ice Cream Boston Admission Ticket

$41
per adult
Museum of Ice Cream Boston Admission Ticket
See all activities in Winchester

Winchester Hotel Deals

Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $167 total per night from Jan 18 to Jan 19
$167 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (1,252 reviews)
Staff were great.

Reviewed on Dec 28, 2025

Hilton Boston Back Bay
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 Jan 11 to Jan 12
$139 total
Jan 11 - Jan 12
Total with taxes and fees
9.2/10 Wonderful! (6,103 reviews)
Very nice boutique hotel nestled right in heart of both downtown and waterfront areas. Joia’s restaurant is wonderful and extremely enjoyable with both ambiance and food quality. Nice find and although it can be a bit pricey, it really is a nice find and very good experience I’d highly recommended ...

Reviewed on Jan 1, 2026

Harborside Inn Of 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
$174 nightly
The price is $203 total per night from Jan 5 to Jan 6
$203 total
Jan 5 - Jan 6
Total with taxes and fees
9/10 Wonderful! (4,363 reviews)
Close to shops and restaurants.

Reviewed on Dec 31, 2025

Omni Boston Hotel at the Seaport
See all 3,975 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 $382 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.