Winchester Vacations from $542

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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.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8/10 Very Good! (2,056 reviews)
Was actually too nice for us

Reviewed on Jul 1, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.6/10 Excellent! (1,999 reviews)
Beautiful hotel! Slow, unfriendly service in restaurant. Missed the free breakfast as we had to leave at 6 for the airport. Would be nice if there were options for early flyers since the hotel caters to airport. Waited an hour at the airport for shuttle to pick us up. 3 calls, first one said 15-20 minutes, second one said 10 minutes out. Third one said any minute.

Reviewed on Jul 6, 2025

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 21
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
10/10 Exceptional! (8 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Beautiful hotel. Perfectly located

Reviewed on Jul 4, 2025

Ocean Air Suites

Ocean Air Suites

2.5 out of 5
Hampton Beach
Save 100% on your flight
per person
Sep 5 - Sep 8
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (32 reviews)
location was awesome. able to see fireworks right from deck in the back. It’s definitely family friendly would definitely be coming back again next year :)

Reviewed on Sep 3, 2024

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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
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
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

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
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$70
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$25
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
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
$276 nightly
The price is $321 total per night from Jul 19 to Jul 20
$321 total
Jul 19 - Jul 20
Total includes taxes and fees
9/10 Wonderful! (3,633 reviews)
"Pool was nice"

Reviewed on Jul 6, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Jul 13 to Jul 14
$214 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (1,354 reviews)
"You can’t beat the location and functionality of this hotel. The layout is a little funky with having to take 2 elevators to get to your room but the large common area you get to from the first elevator, great bar/breakfast, rooftop patio and gym make up for any odd elevator situation. The room is ..."

Reviewed on Jul 3, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
$229 nightly
The price is $267 total per night from Jul 13 to Jul 14
$267 total
Jul 13 - Jul 14
Total includes taxes and fees
9/10 Wonderful! (5,277 reviews)
Location, location, location!
"One block from the harbor, two from the independence trail. Comfortable, spacious room. Would have liked a better selection at the adjoining restaurant but would definitely stay here again,"

Reviewed on Jul 5, 2025

Harborside Inn Of Boston
See all 3,744 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 $542 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.