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! (1,002 reviews)
Well-kept hotel with a great restaurant.
Reviewed on 13 Jan 2026
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 29 Jan to 30 Jan
AU$220
29 Jan - 30 Jan
includes taxes & fees
8.4/10 Very Good! (758 reviews)
Great staff
Reviewed on 5 Jan 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AU$242 per night from 26 Jan to 27 Jan
AU$242
26 Jan - 27 Jan
includes taxes & fees
8.2/10 Very Good! (935 reviews)
Fantastic experience! Great staff! Very comfortable room. Thanks .
Reviewed on 10 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.
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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.
