Winchester Vacations

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Find the Best Winchester Vacation Packages

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
The price is AED 878 per night from Mar 21 to Mar 22
AED 878
AED 1,041 total
includes taxes & fees
21 Mar - 22 Mar
9.4/10 Exceptional! (2,836 reviews)
"A terrific hotel, conveniently located within walking distance of several restaurants and places to visit in the seaport and surrounding Boston area."

Reviewed on 12 March 2025

Seaport Hotel Boston
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is AED 547 per night from Mar 13 to Mar 14
AED 547
AED 637 total
includes taxes & fees
13 Mar - 14 Mar
9/10 Wonderful! (4,873 reviews)
"Fantastic location, friendly and professional staff. The restaurant/bar, Joia, has amazing food and drinks. The bartenders and service staff are also very friendly and welcoming. I can’t wait to come back!! The room was clean and quiet. Very comfortable."

Reviewed on 10 March 2025

Harborside Inn Of Boston
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 AED 511 per night from Mar 23 to Mar 24
AED 511
AED 594 total
includes taxes & fees
23 Mar - 24 Mar
9.4/10 Exceptional! (822 reviews)
"Great stay, would recommend and will be staying again."

Reviewed on 9 March 2025

citizenM Boston Back Bay
See all 3,662 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 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.

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 an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 reviews)

Walk around the campus of Harvard University, a top college in Boston. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 reviews)

After visiting Boston Common, make a plan to see the other sights and activities in Boston. Discover the fascinating museums in this vibrant area, or seek out the local tours.

Boston Common