Winchester Vacation Packages

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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!

Top Winchester Vacation Deals

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
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
While the property was clean and the staff knowledgeable and kind, the marketing including representation of a pool and arcade. While a pool is on site, it’s run by a fitness club. The hours provided by the hotel are meaningless as the fitness club will close the pool to hotel guests allowing their members pool access. The pool restrictions are those of the fitness club. Our adult daughter could not swim with our 10 year old as their specifications of an adult are age 21. The arcade was not open during our two day stay. While a nice hotel, not recommended with children. They do offer a water park for $30/person per day. This is open Fri-Sun.

Reviewed on Jul. 25, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul. 23, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Oct 16 - Oct 19
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Lakeside Inn

Lakeside Inn

2 out of 5
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
7.4/10 Good! (2,188 reviews)
Pleasantly surprised. A little older but staff made up for that. staff was excellent very attentive.

Reviewed on Jul. 21, 2025

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.8/10 Excellent! (374 reviews)
Excellent stay, exceptional service, very close to Boston commons, Harbor, ChinaTown, Beacon Hill, etc. Rooms are roomy. Beds are comfortable, housekeeping staff very accommodating. The gym was excellent, top notch. Ate breakfast room service and at in house restaurant-great meals. Highly recommend.

Reviewed on Jul. 5, 2025

Ready to book your vacation to Winchester?

 

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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
The price is CA $251 per night from Aug 24 to Aug 25
CA $251
CA $348 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,716 reviews)
"This property is in a perfect location in the Seaport. We loved it!"

Reviewed on Jul. 24, 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 CA $259 per night from Aug 10 to Aug 11
CA $259
CA $302 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,487 reviews)
"Great place. Just be prepared that there is no curb drop off or hotel parking, so figure out how you are going to park and get your suitcases there ahead of time. Very modern, good restaurant/coffee bar and large hangout lobby, 10 min walk to Finway area. Highly recommend."

Reviewed on Jul. 23, 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $238 per night from Aug 24 to Aug 25
CA $238
CA $278 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,578 reviews)
"It was wicked awesome"

Reviewed on Jul. 24, 2025

citizenM Boston North Station
See all 3,762 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Discover the most popular places to visit in Winchester

Fenway Park featuring 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
Harvard University which includes a city and heritage architecture

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
Boston Common which includes flowers, a garden and landscape views

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

What to do in Winchester

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
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

CA $46
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from CA $387 on Expedia for your Winchester break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
The off-season is the best time to visit Winchester if you're trying to save. Another tip for scoring cheap Winchester vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Winchester?
With about 3 days, you'll have enough time to experience popular neighbourhoods like North Waltham and Assembly Square during your Winchester vacation. Be sure to also add Tufts University and Burlington Mall to your list of must-sees. Searching for more adventures? Consider exploring outside of Winchester on day trips and tours.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Winchester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your next Winchester getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winchester?
Secure amazing discounts by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchester vacation.
How to plan a trip to Winchester?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Winchester.
  2. Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Winchester.
  3. Set the duration of your trip: Start by compiling a list of the attractions you want to get to in Winchester. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right Winchester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.