Winchester Holidays

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    Better together

    Save up to S$134 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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    Plan, book, and manage your trip all in one place

Top hotels in Winchester

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 S$226 per night from 27 Aug to 28 Aug
S$226
27 Aug - 28 Aug
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"We were recently at this hotel with a large group. We had a wonderful time. The room had beautiful high ceilings and it had a lot of charm. I loved that the bathroom had its own sink and then there was another sink located outside of the actual bathroom. We also really love the large refrigerator, ..."

Reviewed on 18 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 S$370 per night from 3 Sept to 4 Sept
S$370
3 Sept - 4 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 S$215 per night from 27 Aug to 28 Aug
S$215
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Beautiful property and stafg"

Reviewed on 17 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.