Winchester Holidays from £1,106
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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.
Latchis Hotel
Price was £2,409, price is now £1,106 per person
£1,106
per person
25 May - 30 May
just found
Return direct flight included
London (LHR) to Springfield (VSF)
8.6/10 Excellent! (860 reviews)
If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful!
This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back!
Reviewed on 30 Mar 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was £2,577, price is now £1,328 per person
£1,328
per person
25 May - 30 May
just found
Return direct flight included
London (LHR) to Springfield (VSF)
8.8/10 Excellent! (1,000 reviews)
Very pleasant stay! Room was clean staff friendly and breakfast hearty.
Reviewed on 3 Apr 2026
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 £120 per night from 27 Apr to 28 Apr
£120
27 Apr - 28 Apr
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Bathroom should have a safety grab bar in the shower as well as hooks for towels.
Reviewed on 5 Apr 2026
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is £75 per night from 12 Apr to 13 Apr
£75
12 Apr - 13 Apr
includes taxes & fees
6.8/10 (1,001 reviews)
Eletric was out without. Found a note on door at check.in to call and they said no information if reopening. Man was pleasant not his fault he is employee. had to find another place that night. Expedia helped.
Reviewed on 10 Apr 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is £97 per night from 22 Apr to 23 Apr
£97
22 Apr - 23 Apr
includes taxes & fees
8.2/10 Very Good! (956 reviews)
Nice
Reviewed on 29 Mar 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.
