Winchester Holidays

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Your Winchester Holiday

Spend less time planning and more time having awesome adventures with a Winchester holiday package. The neighbourhood of Pleasant Valley, which is great for camping and nature, makes an excellent base for your city getaway. A trip to Winchester is an excellent opportunity to go sightseeing. Make sure you visit popular attractions like Highland Lake, Winchester Historical Society and Ames Plaza Shopping Centre. No matter your travel plans or the size of your budget, organising a tailored Winchester holiday is easy with Expedia.

Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Winchester Historical Society, Laurel Lanes and Platt Hill State Park

Our pick of the best Winchester Hotel Deals

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2/10 Wonderful! (37 reviews)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog ..."

Reviewed on 15 Jul. 2024

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Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Family House On Highland Lake with Dock
Family House On Highland Lake with Dock
Winsted
10/10 Exceptional! (23 reviews)
Weekend Stay
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard."

Reviewed on 3 Sep. 2024

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Family House On Highland Lake with Dock
The Farmington Inn & Suites
The Farmington Inn & Suites
3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
The price is AU$256 per night from 7 Dec to 8 Dec
AU$256
includes taxes & fees
7 Dec - 8 Dec
8.6/10 Excellent! (1,002 reviews)
"We had a lovely stay. The staff were very kind and attentive to all our needs. The room and accommodations were very nice."

Reviewed on 14 Nov. 2024

The Farmington Inn & Suites
See all 635 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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Winchester holiday package cost?
Live it up in Winchester from as low as . We offer a great selection of flights, hotels and rental cars to suit every budget. Land even better deals when you add some activities or tours to your holiday package.
How do I get a cheap travel package to Winchester?
Our Winchester holiday packages promise plenty of savings for the savvy traveller. For the best deals, simply bundle your flights, hotels and extras (such as activities) into a neat and tidy package. But impressive bargains are only the start of your next big adventure. Book with Expedia and and you’ll have over 550 airlines and 1 000 000 hotels across the globe to select from. Whatever your budget, there’s a holiday package with your name on it.
Where should I stay in Winchester?
With interesting attractions like Highland Lake and Winchester Historical Society in this neighbourhood, try to find a hotel situated near them. Laurel Lanes is another Winchester sight that travellers flock to.
How far in advance should I book my Winchester holiday?
To score cheap prices, book early. Airlines generally start selling tickets, along with some of the lowest fares, nearly a year ahead of time. Hotels, activities and car rental should also be booked early to avoid disappointment. If you’re in need of a last-minute getaway in Winchester, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia Winchester travel package include?
That mostly depends on you. You can pick from a variety of Winchester bundles, such as a rental car, hotel and flight. You can also book a hotel and a flight, or a flight with a rental car. Once you’ve made your booking, you can add the fun stuff like activities and experiences. Whatever your perfect Winchester getaway looks like, get set to save!
What should I know before booking a Winchester travel package?
A travel package can be customized for your budget and is a great way to make your money go further. How much you include is your call. Rental cars, hotels and flights — come up with a combination that suits your plans.
Can I choose my airline with a Winchester Expedia holiday package?
You can, and with over 550 airlines to select from globally, you’re not short on choice. Scroll through the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Winchester holiday package?
Your situation can change without warning, so yes. You may be able to amend or cancel your Winchester holiday package for free within 24 hours of booking. For older bookings, you can still make the necessary changes, but your airline, hotel or car rental company may impose a fee. Need more information? Check out our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.