Winchester Holidays from £924
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Your Winchester Holiday
When a city stay is calling, answer it with a holiday package to Winchester. With all your travel needs organised before you leave, all you need to do here is focus on having a ball. If a sightseeing tour is on the to-do list during your trip to Winchester, look around leading attractions like Thomas Aquinas College, Pisgah State Park and Birch Point. Stop dreaming and start adventuring. Explore the broad range of options on Expedia today and put your Winchester holiday plans into motion!
Top Winchester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was £1,016, price is now £924 per person
£924
per person
25 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on 26 Jun 2025
The Shire Woodstock
Price was £1,324, price is now £1,137 per person
£1,137
per person
25 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (929 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants
Reviewed on 12 May 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was £1,086, price is now £959 per person
£959
per person
25 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
I’ve stayed here with my two daughters multiple times and it’s always incredible.
Reviewed on 17 May 2026
Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
Price was £1,224, price is now £1,093 per person
£1,093
per person
25 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know
Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.
Reviewed on 8 Oct 2025
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was £1,187, price is now £1,063 per person
£1,063
per person
25 Jun - 2 Jul
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on 1 Dec 2025
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 Cheshire Childrens Museum |
Top hotels in Winchester
The Colonial Hotel
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
The price is £127 per night from 1 Jun to 2 Jun
£127
1 Jun - 2 Jun
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"One suggestion would be to have coffee and tea available in the lobby. Other than that it was a nice stay."
Reviewed on 25 May 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is £104 per night from 14 Jun to 15 Jun
£104
14 Jun - 15 Jun
includes taxes & fees
8.2/10 Very Good! (983 reviews)
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Reviewed on 26 May 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is £103 per night from 28 May to 29 May
£103
28 May - 29 May
includes taxes & fees
8.6/10 Excellent! (885 reviews)
"The staff was great very helpful!!! Very understanding and had patience with me. Thanks Peace&patience JRC"
Reviewed on 25 May 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. Flight-inclusive packages are ATOL protected.
