Winchester Holidays
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Your Winchester Holiday
When a getaway to the city is calling your name, answer it with a holiday package to Winchester. With all your travel needs organised before you go, all you have to do here is concentrate on having fun. If taking in sights is part of the programme during your trip to Winchester, look around popular attractions like Thomas Aquinas College, Pisgah State Park and Birch Point. Whoever you're escaping with and whatever the size of your budget, your dream Winchester holiday is just a few clicks away with Expedia.
Winchester Holiday
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,750 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Colonial Theatre, Historical Society of Cheshire County and Rhododendron State Park |
Our pick of the best Winchester Hotel Deals
The Colonial Hotel
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,013 reviews)
Clean room pool was cold.
Reviewed on 29 Nov 2025
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
Fully refundableReserve now, pay when you stay
The price is AU$310 per night from 10 Dec to 11 Dec
AU$310
10 Dec - 11 Dec
includes taxes & fees
8.6/10 Excellent! (875 reviews)
Staff was friendly, room was very nice and really appreciate the breakfast.
Reviewed on 25 Nov 2025
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AU$239 per night from 11 Dec to 12 Dec
AU$239
11 Dec - 12 Dec
includes taxes & fees
8.2/10 Very Good! (923 reviews)
Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n ...
Reviewed on 20 Nov 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.
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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.
