- 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.
Fairmont Copley Plaza, Boston
Back Bay
per person
23 Mar - 27 Mar
found 1 day ago
Return direct flight included
Cork (ORK) to Boston (BOS)
8.8/10 Excellent! (1,014 reviews)
A little outdated despite the gorgeous architecture.
Also got placed in a king suite with a connecting door to another guest’s room and we could hear EVERYTHING. Some front desk staff were really nice and welcoming whereas others weren’t so kind.
Reviewed on 29 Jan 2025
Boston Harbor Hotel
North End
per person
23 Mar - 27 Mar
found 1 day ago
Return direct flight included
Cork (ORK) to Boston (BOS)
9.6/10 Exceptional! (1,006 reviews)
The views to the harbor were beautiful! The large windows are amazing to enjoy the view in the room. The service was excellent! Great attention to small details!! Just need to improve their menu for better food options for vegetarians/vegans. Other than that, I look forward to returning!
Reviewed on 28 Jan 2025
Raffles Boston
Back Bay
per person
23 Mar - 27 Mar
found 1 day ago
Return direct flight included
Cork (ORK) to Boston (BOS)
9.6/10 Exceptional! (93 reviews)
It’s my second time staying at a Raffles and it maintains the same level of hospitality and luxury comfort in Boston. Thank you.
Reviewed on 21 Jan 2025
Top hotels in Winchester
Seaport Hotel Boston
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €216 per night from 16 Feb to 17 Feb
€216
includes taxes & fees
16 Feb - 17 Feb
9.6/10 Exceptional! (2,750 reviews)
"Night club and kids friendly"
Reviewed on 30 Jan 2025
Hilton Boston Park Plaza
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €164 per night from 23 Feb to 24 Feb
€164
includes taxes & fees
23 Feb - 24 Feb
8.2/10 Very Good! (3,289 reviews)
"Beautiful Lobby. Had an excellent Old Fashioned"
Reviewed on 27 Jan 2025
Harborside Inn Of Boston
185 State St, Boston, MA
The price is €122 per night from 2 Feb to 3 Feb
€122
includes taxes & fees
2 Feb - 3 Feb
9/10 Wonderful! (4,620 reviews)
"Wonderful service, welcoming, very cool hotel super conveniently located next to Faneuil Hall. Close to highways and parking garage conveniently around the corner."
Reviewed on 28 Jan 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.
Frequently asked questions
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.
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.
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.
What to do in Winchester
View Boston Observation Deck Admission Tickets
€24
per adult
78% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
€71
per adult
90% of travellers recommend
New York City Day Tour from Boston
€164
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.