
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
8.6/10 Excellent! (1,006 reviews)
"Beautiful property. There were a few things that could’ve been updated but overall we had a nice stay. It was very clean and quiet. The staff was wonderful."
Reviewed on 9 Jun. 2025

Comfort Inn & Suites Brattleboro I-91
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 3 July to 4 July
AU$221
3 July - 4 July
includes taxes & fees
8.6/10 Excellent! (639 reviews)
"Staff was very helpful and easy access to the interstate."
Reviewed on 9 Jun. 2025

Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
The price is AU$214 per night from 29 June to 30 June
AU$214
29 June - 30 June
includes taxes & fees
8/10 Very Good! (831 reviews)
"Our stay was good. Staff on the phone wasn’t the most friendly. We asked for an early check in since we were traveling with a baby and were told to keep calling to check for availability. We did so. However, by the time of our last call the staff member on the phone wasn’t kind and made us feel like ..."
Reviewed on 7 Jun. 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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.