Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

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!

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

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,001 reviews)
Pleasantly surprised! Lovely place!
"The Colonial Hotel is absolutely breathtaking! Really well kept and the staff was so friendly! Comfortable beds and pillows! Nice sauna, hot tub and small gym. We dined at the restaurant and had a great experience and service there as well!"

Reviewed on 9 Aug 2025

Get rates
The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is £114 per night from 12 Aug to 13 Aug
£114
12 Aug - 13 Aug
includes taxes & fees
6.6/10 (1,002 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on 28 Jul 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is £99 per night from 4 Sept to 5 Sept
£99
4 Sept - 5 Sept
includes taxes & fees
8/10 Very Good! (862 reviews)
"Didn’t like the fact that I was suppose to be charge when I checked in but they charged my card before I arrived."

Reviewed on 9 Aug 2025

Hampton Inn Brattleboro
See all 414 properties in Winchester
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Winchester travel package cost?
Handcraft your Winchester package from just . Choose from any combination of rental cars, flights and hotels to create the trip you've been dreaming about for ages. Remember to add on some tours and experiences!
If I'm not able to travel, can I cancel my Winchester travel package?
Yes, you can cancel your Winchester booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Winchester?
Track down flights that fit your schedule, add a hotel room to your booking and watch the savings grow with a Winchester travel package. It's as simple as that! From flights and hotels to rental cars and tours, Expedia is your gateway to cheap travel. And with more than 550 partner airlines and 1,000,000 hotels all over the world to choose from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Expedia has joined forces with online lender Klarna to make booking your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next adventure, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that fit all budgets, so you can book that well-earned holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip in multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is much easier with this option. Put down a small deposit on your booking and then start working on your travel itinerary.

What are the top hotels in Winchester?
Get your escape off to an excellent start by reserving a room at Green Granite Inn. It's one of most popular hotels in Winchester. Another cosy option is Hampton Inn & Suites Portsmouth Downtown.
How far in advance should I book my Winchester holiday?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't fret. Cheap prices occasionally appear within a few weeks of departure dates.
What does an Expedia Winchester travel package include?
With Expedia, you can select any combination of flights, car rentals and hotels to create your perfect Winchester package. Once you've made your booking, you can add on the fun things like tours and experiences. Remember, the more you bundle, the bigger the savings!
What should I know before booking a Winchester travel package?
A travel package can be easier on the hip pocket than separately booking everything you need for your trip. For example, combine your flights, hotels and rental cars and save a tidy sum. Whatever sort of holiday you're planning, you'll find a package to suit your budget.
Can I choose my airline with a Winchester Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.

* 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.