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.

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

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd, Avon, CT
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 2 Sept to 3 Sept
AU$207
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Did feel safe on our end room arriving late at night."

Reviewed on 23 Aug. 2025

Avon Old Farms Hotel
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
The price is AU$458 per night from 1 Sept to 2 Sept
AU$458
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"My only complaint is your parking garage. It is terrifyingly dark. Had I been alone? I'd never have parked there!!!"

Reviewed on 21 Aug. 2025

Sheraton Hartford Hotel at Bradley Airport
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$248 per night from 28 Aug to 29 Aug
AU$248
28 Aug - 29 Aug
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Very nice area, friendly Service, best Eagles for breakfast"

Reviewed on 25 Aug. 2025

The Farmington Inn & Suites
See all 675 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?
You'll find cheap prices on Expedia for your Winchester escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
Plan your getaway for the shoulder or low season and you're likely to score cheap Winchester holiday packages. Bear in mind that school holiday periods and major events and festivals can impact prices, so do your research before booking.
How many days is enough for Winchester?
The ideal duration for your Winchester holiday depends on what you'd like to see and do. Typically, a few days to a week will give you time to check out all the main sights and explore some hidden gems along the way.
How to find the best Winchester package deals?
Use Expedia's filters to help you find some great Winchester package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Winchester package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Winchester holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a customised Winchester holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Winchester?
If you've got your Winchester travel dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Winchester?

  1. Pick your dates: The things you want to do in Winchester and your favourite season can help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Winchester.
  3. Work out your trip length: Think about how much time you want to spend exploring Winchester. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodation: Once you've settled on your trip dates and duration, lock in the right Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.