Winchester Trips (flight + hotel)

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Top hotels in Winchester

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
The price is P13,076 per night from Jul 19 to Jul 20
P13,076
P17,532 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,598 reviews)
"Great hotel!"

Reviewed on Jun 26, 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
The price is P7,872 per night from Jul 6 to Jul 7
P7,872
P9,167 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,316 reviews)
"Friendly and helpful staffs, excellent team!"

Reviewed on Jun 27, 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is P13,404 per night from Jul 1 to Jul 2
P13,404
P15,892 total
Jul 1 - Jul 2
includes taxes & fees
9.6/10 Exceptional! (2,990 reviews)
"We enjoy the Seaport Area of Boston and found this hotel very comfortable and convenient. We greatly appreciated that they do not add a daily “resort” fee like some nearby hotels."

Reviewed on Jun 25, 2025

Seaport Hotel Boston
See all 3,743 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.

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices 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?
Plan your trip for the shoulder or low season and you're likely to find cheap Winchester vacation packages. Keep in mind that public holidays and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Winchester?
Usually, a handful of days is enough to check out the major attractions during your Winchester vacation. But if you'd like to have some time to rest or take day tours, think about extending your trip.
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.
How to plan a trip to Winchester?

  1. Choose your travel dates: The things you'd like to do in Winchester and your favorite season will help you decide when to go.
  2. Set your budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Winchester. Then, pick a hotel that works with your budget, whether that's an affordable option or a more luxurious retreat.
  3. Decide how many days away: Start by listing all the attractions you want to experience in Winchester. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Winchester vacation package for you.

Popular places to visit

Harvard University which includes heritage architecture and a city

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
New England Aquarium

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium
Massachusetts showing outdoor eating, a house and cafe lifestyle

Newbury Street

Stretching between Massachusetts Avenue and Boston Public Gardens, this upscale street is one of Boston’s most popular shopping and dining destinations.

Newbury Street

What to do in Winchester

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

P4,438
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

P3,942
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

P1,898
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Winchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.