Winchester Holidays
Photo by Ana Lei
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Top Flight + Hotel Deals in Winchester
Price found within the past 48 hours. Click for updated prices.
The Newbury Boston
Back Bay
Price was €1,767, price is now €1,310 per person
€1,310
per person
25 Jan - 30 Jan
found 4 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Very friendly staff. Amazing location. The room was perfect. Didn’t go to Contessa, but we ran into the Chef in the elevator and he was super fun and courteous. The bar is cool, we ate there a couple nights. We had a very pleasant Thanksgiving week there. Festive and lively hotel. There’s Tatte around the corner and every store you can think of within walking distance. Looking forward to our next stay!
Reviewed on 4 Dec 2025
The Charles Hotel
West Cambridge
Price was €1,083, price is now €926 per person
€926
per person
20 Jan - 23 Jan
found 9 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
We love the Charles Hotel. From its helpful and friendly staff, spotless and well appointed rooms, and excellent on-site restaurants. It is the perfect place for a winter getaway.
Reviewed on 14 Dec 2025
Top hotels in Winchester
Harborside Inn Of Boston
185 State St Boston MA
The price is €106 per night from 21 Dec to 22 Dec
€106
21 Dec - 22 Dec
includes taxes & fees
9.2/10 Wonderful! (6,064 reviews)
The hotel has a very authentic and chic décor, with a great atmosphere. The staff was friendly, and the location is excellent — very convenient and within walking distance to most attractions. A couple of small issues (housekeeping and the TV) were resolved promptly after I reported them. I did not ...
Reviewed on 15 Dec 2025
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is €214 per night from 1 Jan to 2 Jan
€214
1 Jan - 2 Jan 2026
includes taxes & fees
9/10 Wonderful! (4,283 reviews)
.
Reviewed on 11 Dec 2025
Hilton Boston Back Bay
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is €166 per night from 21 Dec to 22 Dec
€166
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (1,242 reviews)
Yes to all of the above
Reviewed on 9 Dec 2025
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.
Popular places to visit
Fenway Park
4.5/5(61 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
4.5/5(102 reviews)
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
TD Garden
4.5/5(42 reviews)
Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.
What to do in Winchester
Boston CityPASS®: Admission to Top 4 Attractions
€68
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
€26
per adult
88% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
€72
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
