Winchester Holidays
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Top Flight + Hotel Deals in Winchester
Price found within the past 48 hours. Click for updated prices.
The Whitney Hotel
Beacon Hill
Price was €1,984, price is now €1,483 per person
€1,483
per person
22 Mar - 27 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Clean room that satisfied all needs. Great location in a quaint neighborhood
Reviewed on 30 Jan 2026
Hilton Boston Back Bay
Fenway–Kenmore
Price was €1,461, price is now €1,181 per person
€1,181
per person
5 Apr - 10 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (1,229 reviews)
Room is amazing
I love how room service even fold our pajama. Impeccable into details. They sent a microwave to our room as per request.
I hope they have Hot Water ready in lobby 24/7. Access to that is very limited
Reviewed on 20 Jan 2026
Top hotels in Winchester
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is €187 per night from 5 Feb to 6 Feb
€187
5 Feb - 6 Feb
includes taxes & fees
9.6/10 Exceptional! (3,937 reviews)
Wonderful staff and great experience!
Reviewed on 28 Jan 2026
Harborside Inn Of Boston
185 State St Boston MA
The price is €114 per night from 3 Feb to 4 Feb
€114
3 Feb - 4 Feb
includes taxes & fees
9.2/10 Wonderful! (6,189 reviews)
Clean, comfortable bed
Reviewed on 26 Jan 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is €77 per night from 2 Feb to 3 Feb
€77
2 Feb - 3 Feb
includes taxes & fees
9/10 Wonderful! (2,423 reviews)
The front desk lady was friendly and helpful. The room and bathrooms were extremely clean. The hotel had a great vibe. At the price, it exceeded my expectations.
Reviewed on 27 Jan 2026
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
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
TD Garden
Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.
Harvard University
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
Boston CityPASS®: Admission to Top 4 Attractions
€67
per adult
92% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
€72
per adult
80% of travellers recommend
View Boston Observation Deck Admission Tickets
€29
per adult
88% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
