Name: The Dagny Boston
Price range: AU$724
Rating: 9.4

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.

The Beverly

AU$3,122

per person

27 Dec - 2 Jan

found 21 hours ago

Return direct flight included

Sydney (SYD) to Boston (BOS)

8.4/10 Very Good! (343 reviews)

Clean room Easy check in. Walkable to Salem Nice hotel overall. Will definitely stay again

Reviewed on 3 Oct 2025

Raffles Boston

Back Bay

AU$4,422

per person

27 Dec - 2 Jan

found 23 hours ago

Return flight included

Sydney (SYD) to Boston (BOS)

9.8/10 Exceptional! (160 reviews)

Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!

Reviewed on 15 Sept 2025

Boston Harbor Hotel

North End

AU$4,572

per person

27 Dec - 2 Jan

found 23 hours ago

Return flight included

Sydney (SYD) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Easy access to mass transit and to all the downtown areas of interest.

Reviewed on 4 Oct 2025

Lakeside Inn

AU$3,232

per person

27 Dec - 2 Jan

found 21 hours ago

Return direct flight included

Sydney (SYD) to Boston (BOS)

7.4/10 Good! (2,176 reviews)

My only complaint is my bathroom door would not latch and you have to use you entire body to open the door to enter.

Reviewed on 4 Oct 2025

The Wylie Inn and Conference Center at Endicott College

AU$3,163

per person

27 Dec - 2 Jan

found 21 hours ago

Return direct flight included

Sydney (SYD) to Boston (BOS)

9.2/10 Wonderful! (1,092 reviews)

Did not use computer

Reviewed on 5 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

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Fully refundableReserve now, pay when you stay

AU$483

30 Oct - 31 Oct

includes taxes & fees

9/10 Wonderful! (4,091 reviews)

"Great experience"

Reviewed on 3 Oct 2025

citizenM Boston North Station

70 Causeway Street, Boston, MA

Fully refundableReserve now, pay when you stay

AU$465

2 Nov - 3 Nov

includes taxes & fees

9.2/10 Wonderful! (3,848 reviews)

"We loved our stay at CitizenM."

Reviewed on 1 Oct 2025

The Dagny Boston

89 Broad Street, Boston, MA

AU$724

12 Oct - 13 Oct

includes taxes & fees

9.4/10 Exceptional! (6,521 reviews)

"Amazing hotel and location"

Reviewed on 30 Sept 2025

See all 3,769 properties in Winchester

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.