Winchester Holidays
Photo by Ana Lei
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Winchester
Price found within the past 48 hours. Click for updated prices.
XV Beacon
Beacon Hill
Price was €1,437, price is now €1,095 per person
€1,095
per person
11 Nov - 15 Nov
found 8 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (377 reviews)
The hotel is a beautiful boutique hotel with everything a person needs in a city! The rooms are spacious and nicely appointed, the staff is great and the food amazing. What more could you want. Oh...there is a car to drive you to dinner or somewhere in the city if you need a ride!
Reviewed on 16 Jun 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was €1,869, price is now €1,428 per person
€1,428
per person
11 Nov - 15 Nov
found 8 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,028 reviews)
Great location. Reliable accommodation.
Reviewed on 4 Sep 2025
Top hotels in Winchester
Seaport Hotel Boston
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €276 per night from 6 Sept to 7 Sept
€276
6 Sept - 7 Sept
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €274 per night from 6 Sept to 7 Sept
€274
6 Sept - 7 Sept
includes taxes & fees
citizenM Boston North Station
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €209 per night from 21 Sept to 22 Sept
€209
21 Sept - 22 Sept
includes taxes & fees
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.
New England Aquarium
4.5/5(57 reviews)
From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.
What to do in Winchester
Boston CityPASS®: Admission to Top 4 Attractions
€68
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
€29
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
