Winchester Holidays from AU$1,071
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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.
Battery Wharf Hotel, Boston Waterfront
North End
Price was AU$1,452, price is now AU$1,071 per person
AU$1,071
per person
29 Dec - 1 Jan
found 2 hours ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
8.6/10 Excellent! (1,687 reviews)
Perfect location, modern and nice surroundings.
Reviewed on 17 Oct 2025
The Whitney Hotel
Beacon Hill
Price was AU$1,829, price is now AU$1,226 per person
AU$1,226
per person
29 Dec - 1 Jan
found 2 hours ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.
Reviewed on 13 Oct 2025
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was AU$1,997, price is now AU$1,346 per person
AU$1,346
per person
29 Dec - 1 Jan
found 2 hours ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.6/10 Exceptional! (1,008 reviews)
Great location with easy walking to other districts.
Fabulous old hotel full of history but that has been tastefully renovated and upgraded.
Lovely hotel and our stay was made even better with the wonderful staff - a big thank you to Jenna on the concierge desk who gave us some fabulous restaurant recommendations and to Saleem on reception.
Reviewed on 14 Oct 2025
The Newbury Boston
Back Bay
Price was AU$1,868, price is now AU$1,275 per person
AU$1,275
per person
29 Dec - 1 Jan
found 2 hours ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
Great location but they have no concierge , and for the price you will think they would. Rooms are small
Reviewed on 8 Oct 2025
XV Beacon
Beacon Hill
Price was AU$2,212, price is now AU$1,618 per person
AU$1,618
per person
29 Dec - 1 Jan
found 2 hours ago
Return direct flight included
Memphis (MEM) to Boston (BOS)
9.4/10 Exceptional! (377 reviews)
This is a classy boutique hotel, friendly staff who go the extra mile and keep the property looking sharp. The Moo restaurant is a real hotspot in the area, great food. The location is just where you wanna be in Boston.
Reviewed on 3 Oct 2025
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
The Revolution Hotel
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 9 Nov to 10 Nov
AU$225
9 Nov - 10 Nov
includes taxes & fees
8.8/10 Excellent! (2,172 reviews)
"Fast check in very convenient exactly what you need it for. Well decorated"
Reviewed on 12 Oct 2025
citizenM Boston North Station
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$321 per night from 16 Nov to 17 Nov
AU$321
16 Nov - 17 Nov
includes taxes & fees
9.2/10 Wonderful! (3,913 reviews)
"The staff was great, and the hotel is in a great location in the middle of a lot of things. Everything is walkable, and transportation is easy. The view is amazing. I will be coming back!"
Reviewed on 13 Oct 2025
The Dagny Boston
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$554 per night from 31 Oct to 1 Nov
AU$554
31 Oct - 1 Nov
includes taxes & fees
9.4/10 Exceptional! (6,597 reviews)
"The staff was responsive and got me everything I needed within minutes. The rooms were clean and looked great."
Reviewed on 13 Oct 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.
Discover the most popular places to visit in Winchester
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Boston Common
The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.
What to do in Winchester
Boston Harbor New England Aquarium Whale-Watching Cruise
AU$122
per adult
86% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
AU$128
per adult
76% 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.
