
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! (1,008 reviews)
"Nice place"
Reviewed on 9 Oct 2025

Econo Lodge Brattleboro
515 Canal St, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 13 Nov to 14 Nov
AU$115
13 Nov - 14 Nov
includes taxes & fees
5.4/10 (578 reviews)
Fine room, right next to I-91 exit.
"Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables ..."
Reviewed on 2 Sept 2025

Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 26 Oct to 27 Oct
AU$208
26 Oct - 27 Oct
includes taxes & fees
8.4/10 Very Good! (920 reviews)
"Staff was very cordial. Our 2 day stay was perfect!"
Reviewed on 12 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.
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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.