Winchester Holidays from £783

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Your Winchester Holiday

The best way to experience this unique city is with a tailor-made Winchester holiday package. Base yourself in the neighbourhood of New Hartford, which is good for nature, history and skiing or choose someplace else — our package deals are all about you. Make your trip to Winchester even more enjoyable by going sightseeing. Highland Lake, Laurel Lanes and Winchester Historical Society are some of the leading attractions you'll want to explore. Whatever your travel plans or budget, organising your ultimate tailored Winchester holiday is easy with Expedia.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
29 Sept - 6 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
8.2/10 Very Good! (622 reviews)
Everything was perfect!

Reviewed on 27 Jul 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
29 Sept - 6 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Pillows are horrible.

Reviewed on 9 Aug 2025

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
per person
29 Sept - 6 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Always enjoy staying at this property as it close to the freeway and have in close proximity to restaurants.

Reviewed on 5 Aug 2025

Comfort Inn & Suites East Hartford - Hartford

Comfort Inn & Suites East Hartford - Hartford

2.5 out of 5
per person
29 Sept - 6 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
7.6/10 Good! (1,001 reviews)
The property was decent. There was a dirty tub with a ring around it. Good thing my girlfriend and I brought cleaning products. There are no microwaves In the rooms. The beds are super soft which and be a plus or a minus for some people. They have good standard hotel breakfast.

Reviewed on 6 Aug 2025

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
29 Sept - 6 Oct
found 1 day ago
Return direct flight included
London (LHR) to New Haven (HVN)
9/10 Wonderful! (1,003 reviews)
Spacious and clean. Staff was kind.

Reviewed on 3 Aug 2025

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

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 £111 per night from 14 Aug to 15 Aug
£111
14 Aug - 15 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"C"

Reviewed on 9 Aug 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 £146 per night from 12 Aug to 13 Aug
£146
12 Aug - 13 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"This is a large property with comfortable amenities at a good price. The free breakfast is standard fare, scrambled egg, bacon, sausage, and potatoes with the choice of breads for toast. They also offer some breakfast cereals and Chobani yogurt. The outdoor pool was wonderful, situated next to a ..."

Reviewed on 4 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 £214 per night from 1 Sept to 2 Sept
£214
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Access to the airport"

Reviewed on 5 Aug 2025

Sheraton Hartford Hotel at Bradley Airport
See all 672 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?
Customize your Winchester package from just £783. Choose from any combination of hotels, flights and rental cars to put together the escape you've been dreaming of. Don't forget to add on one or two experiences!
If I'm not able to travel, can I cancel my Winchester travel package?
If your holiday plans in Winchester have changed, it's comforting to know that it's possible to cancel or amend your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Winchester?
Crafting your own Winchester travel package with Expedia is one of the easiest ways to save. We have more than 550 air carriers and 1,000,000 hotel options across the globe. With such an extensive range to select from, you'll have no worries pulling together your perfect escape.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If paying bite-sized amounts each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in Winchester?
A trip to Winchester isn't complete without paying a visit to Winchester Historical Society, Laurel Lanes and Highland Lake. Stay close to these sights and make sightseeing easy.
What are the top hotels in Winchester?
Rock Hall Luxe Lodging and Enjoy A Restful Stay With Fast Internet are a couple of the most sought-after hotels in Winchester. Why not look up the facilities and rates at each and then make a decision?
How far in advance should I book my Winchester holiday?
Your safest bet is to book early. Air carriers typically release flights up to 12 months ahead of departure, and this is when you can pick up some of the cheapest prices. Boss just told you to use up your holiday time in a few weeks? Don't fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Winchester travel package include?
Rental cars, hotels and flights, or any combination of the three — it's your pick! Whether you're visiting Winchester with the kids or travelling by yourself, there's a bundle to suit every budget and style. Once you've made your booking, why not add on a couple of tours or activities?
What should I know before booking a Winchester travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and pick up fantastic discounts. Hotels aren't your only choice, though. Book with us and take your pick of island villas, chalets in the middle of mountains and even houseboats and castles!
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 worldwide. Our travel packages give you the flexibility 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.