Winchester Holidays from AU$2,719
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Your Winchester Holiday
Lock in a Winchester holiday package that has everything you need and no unnecessary extras. Great for nightlife, shopping and bars and pubs, consider staying in the neighbourhood of Downtown Boston. You'll want to sightsee during your trip to Winchester. Drop by leading attractions such as Harvard Square, Harvard University and Bentley College. Expedia is here to help you escape your daily routine. Tailor your holiday to Winchester to match your travel style, whatever that may be.
The Latest Winchester Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Boston/Cambridge
MIT
Price was AU$3,495, price is now AU$2,719 per person
AU$2,719
per person
9 Apr - 16 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9/10 Wonderful! (2,215 reviews)
Convenient and clean. Love the glass atrium and the views of the Charles River.
Reviewed on 16 Jan 2026
Fairmont Copley Plaza, Boston
Back Bay
Price was AU$4,974, price is now AU$3,745 per person
AU$3,745
per person
9 Apr - 16 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Location was perfect, staff was wonderful and the foyer and lobby and the bar/ restaurant was amazing! The guest rooms were good, bed was comfortable and room was immaculate! My only complaint would be the water pressure in the shower was weak! Other than that a very good experience!
Reviewed on 13 Jan 2026
The Verb Hotel
Fenway–Kenmore
Price was AU$4,669, price is now AU$3,559 per person
AU$3,559
per person
9 Apr - 16 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (1,928 reviews)
It was a beautiful room with friendly staff, a comfy bed, and nitro brewed coffee on demand
Reviewed on 18 Jan 2026
Eurostars The Boxer
West End
Price was AU$3,580, price is now AU$2,754 per person
AU$2,754
per person
9 Apr - 16 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Amazing hotel and staff that made my partner and I’s trip amazing!
Reviewed on 18 Jan 2026
Winchester Holiday
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Logan Intl. Airport (BOS) |
Population | 21,400 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | New England Aquarium, Boston Museum of Fine Arts and Museum of Science |
Our pick of the best Winchester Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 25 Jan to 26 Jan
AU$233
25 Jan - 26 Jan
includes taxes & fees
9.6/10 Exceptional! (3,898 reviews)
The rooms nice. Towels not so good
Reviewed on 15 Jan 2026
Harborside Inn Of Boston
185 State St Boston MA
The price is AU$187 per night from 25 Jan to 26 Jan
AU$187
25 Jan - 26 Jan
includes taxes & fees
9.2/10 Wonderful! (6,161 reviews)
Nice bed and homely facilities. Great staff
Reviewed on 13 Jan 2026
The Langham, Boston
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$653 per night from 23 Jan to 24 Jan
AU$653
23 Jan - 24 Jan
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
Amazing service and staff
Reviewed on 15 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.
Discover the most popular places to visit in Winchester
Fenway Park
4.5/5(9 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Boston Common
4.5/5(32 reviews)
The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.
TD Garden
4.5/5(6 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
Go City: Boston All-Inclusive Pass with 45+ Attractions
AU$125
per adult
80% of travellers recommend
The Full Revolutionary Story Epic Small Group Boston Walking Tour
AU$82
per adult
100% of travellers recommend
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions
AU$81
per adult
98% 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.
