Winchester Vacations from $405
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Your Winchester Vacation
The best way to experience this unique city is with a tailor-made Winchester vacation package. Base yourself in the neighborhood 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, organizing your ultimate tailored Winchester vacation is easy with Expedia.
The Latest Winchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Price was $505, price is now $405 per person
$405
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
17.6/10 Exceptional! (1,004 reviews)
Spotless rooms, everywhere was clean. Staff was great.
Reviewed on Nov 17, 2025
Residence Inn by Marriott Southington
Price was $735, price is now $548 per person
$548
per person
Dec 26 - Dec 31
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to New Haven (HVN)
17.2/10 Exceptional! (581 reviews)
A awesome place to stay whether just traveling through or staying in the area. Easy on and off the Interstate with lots of parking. A great staff from front desk to breakfast servers. Everyone made us feel at home. The rooms are spacious and feels like you are home not a hotel/motel/suite. Will definitely stay here again in the near future and recommend anyone traveling through to stop in and stay the night.
Reviewed on Nov 17, 2025
Springhill Suites by Marriott Mystic Waterford
Price was $586, price is now $450 per person
$450
per person
Jan 31 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
17.2/10 Exceptional! (915 reviews)
The staff was incredible! Especially the front desk team! They were so friendly and kind!
Reviewed on Oct 29, 2025
Holiday Inn Express Southington by IHG
Price was $658, price is now $520 per person
$520
per person
Dec 26 - Dec 31
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to New Haven (HVN)
17.2/10 Exceptional! (1,149 reviews)
The rooms are nice and the staff is accommodating. The fitness center could use an upgrade
Reviewed on Nov 22, 2025
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Price was $1,012, price is now $831 per person
$831
per person
Dec 31 - Jan 4
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to New Haven (HVN)
17.6/10 Exceptional! (1,827 reviews)
Friendly staff, spotless’s room and very conveniently located up the street from Mohegan Sun. Very good value.
Reviewed on Nov 23, 2025
Discover the most popular places to visit in Winchester
Winchester Historical Society
You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.
Winchester Hotel Deals
Extended Stay America Suites Hartford Farmington
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from Dec 5 to Dec 6
$109 total
Dec 5 - Dec 6
Total with taxes and fees
7.8/10 Good! (999 reviews)
Staff was very courteous. Room was very clean. Loved it. Will definitely be back.
Reviewed on Nov 15, 2025
Sheraton Hartford Hotel at Bradley Airport
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $286 total per night from Dec 1 to Dec 2
$286 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
Ordered room service and it came very quickly. Hotel is under renovation and is very nice. Will say that walls are not well insulated because you can hear a lot of what’s going on in other rooms.
Reviewed on Nov 19, 2025
Avon Old Farms Hotel
279 Avon Mountain Rd Avon CT
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $150 total per night from Dec 1 to Dec 2
$150 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
This is a beautiful classic hotel with impeccable service. The grounds are so gorgeous!
Reviewed on Nov 6, 2025
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.
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Top Sights | Winchester Historical Society, Laurel Lanes and Platt Hill State Park |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
