Winchester Holidays

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Top hotels in Winchester

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 Rp2.105.280 per night from 31 Jul to 1 Aug
Rp2.105.280
Rp2.702.592 total
31 Jul - 1 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Nice !
"Comfortable stay , nice staff , plenty of parking , nice walkable neighborhood, nice breakfast spread , gym on sight , clean and if you want to go swimming in a awesome indoor pool with in ground jacuzzi they have a sister hotel named Simsbury Inn about 25 minutes away where you can attend free up ..."

Reviewed on 26 Jul 2025

The Farmington Inn & Suites
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 Rp2.482.272 per night from 29 Jul to 30 Jul
Rp2.482.272
Rp3.211.205 total
29 Jul - 30 Jul
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Staff was very friendly and professional. Room in old building on second floor had severely cracked concrete walkway outside with exposed rebar. Metal outdoor stairs to second floor were very rusty and needed painting. Changed to larger room in upper building. Both rooms very musty. Need fan in bathroom ..."

Reviewed on 27 Jul 2025

Avon Old Farms Hotel
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd, Farmington, CT
Fully refundableReserve now, pay when you stay
The price is Rp1.821.149 per night from 3 Aug to 4 Aug
Rp1.821.149
Rp2.094.346 total
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (962 reviews)
"I enjoyed my stay. It was a little home away from home."

Reviewed on 9 Jul 2025

Extended Stay America Suites Hartford Farmington
See all 671 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.