Winchester Holidays
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Top Flight + Hotel Deals in Winchester
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Boston/Cambridge
MIT
Price was €1,114, price is now €1,114 per person
€1,114
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,370 reviews)
Good hotel , amenities and onsite restaurant is good. A 20 walk from central Cambridge , but shuttle bus available
Safe area and MIT campuses located close by.
Ideal for people looking for a peaceful location in a good quality hotel , and easy reach of central Cambridge / Boston and Harvard
Reviewed on 25 Jun 2026
Mandarin Oriental, Boston
Back Bay
Price was €3,793, price is now €2,439 per person
€2,439
per person
29 Jul - 4 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (428 reviews)
The valet was fast and professional, the room was clean, the staff are very helpful. I would definitely stay again!
Reviewed on 25 May 2026
The Godfrey Hotel Boston
Downtown Boston
Price was €1,849, price is now €1,324 per person
€1,324
per person
29 Jul - 4 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (5,092 reviews)
The hotel and staff were very friendly and clean. The best part was the location, just a short walk from Boston Common, the Freedom Trail, and more. The two restaurants at the hotel were very good. A breakfast place with amazing coffee and a Peruvian restaurant that was completely enjoyable!.
We have added the Godfrey to future visits to Boston.
Reviewed on 25 Jun 2026
Top hotels in Winchester
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is €147 per night from 30 Jun to 1 Jul
€147
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (2,699 reviews)
"Interesting , unique hotel in a nice neighborhood"
Reviewed on 26 Jun 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is €189 per night from 2 Jul to 3 Jul
€189
2 Jul - 3 Jul
includes taxes & fees
9/10 Wonderful! (2,388 reviews)
"Staff was amazing! View from our balcony was amazing!!"
Reviewed on 25 Jun 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is €224 per night from 5 Jul to 6 Jul
€224
5 Jul - 6 Jul
includes taxes & fees
9.6/10 Exceptional! (4,473 reviews)
"Conveniently located, excellent service"
Reviewed on 26 Jun 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.
Stay near popular Winchester attractions
What to do in Winchester
Boston Old Town Trolley Hop-on Hop-Off City Tour
€45
per adult
90% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
€39
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
€31
per adult
98% of travellers recommend
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