Winchester Vacations from $317

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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 & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Save 100% on your flight
Price was $451, price is now $317 per person
$317
per person
Jan 5 - Jan 9
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (103 reviews)
Didnt know there wasnt continental breakfast, the water took 20 minutes to warm up, the air conditioning in the room was faulty, a wall strip on a corner was dangling off, and there was a weird diver in the floor next to the shower. We werent there much so it wasnt a super big deal but it felt like a new construction project that cut corners

Reviewed on Oct 22, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $988, price is now $469 per person
$469
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,528, price is now $921 per person
$921
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on Oct 13, 2025

Lakeside Inn

Lakeside Inn

2 out of 5
Save 100% on your flight
Price was $750, price is now $496 per person
$496
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
7.4/10 Good! (2,254 reviews)
This is an amazing piece place to stay and the good from their diner is amazing!

Reviewed on Oct 26, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
Jeffries Point
Price was $829, price is now $555 per person
$555
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (2,117 reviews)
Everthing was all nice

Reviewed on Oct 26, 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
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: Scenic Moonlight Harbor Cruise

Boston: Scenic Moonlight Harbor Cruise

$33
per adult
Boston: Scenic Moonlight Harbor Cruise
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$54
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
See all activities in Winchester

Winchester Hotel Deals

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Nov 23 to Nov 24
$108 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (2,186 reviews)
Shared bathrooms worked really well. Downstairs area was lovely

Reviewed on Oct 25, 2025

The Revolution Hotel
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
$182 nightly
The price is $212 total per night from Nov 24 to Nov 25
$212 total
Nov 24 - Nov 25
Total with taxes and fees
9/10 Wonderful! (4,178 reviews)
room is very clean ,good location , facilities are great .

Reviewed on Oct 22, 2025

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $225 total per night from Nov 23 to Nov 24
$225 total
Nov 23 - Nov 24
Total with taxes and fees
9.6/10 Exceptional! (3,598 reviews)
It was a really lovely hotel in a great area. I did feel the carpets in reception desperately needed a clean, which I felt let it down as the rest of the hotel and the rooms were spotless

Reviewed on Oct 25, 2025

Seaport Hotel Boston
See all 3,858 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 $317 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.