Winchester Vacations from $338
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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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was $391, price is now $338 per person
$338
per person
Apr 10 - Apr 12
found 18 hours ago
Roundtrip flight included
Houston (IAH) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question.
Reviewed on Feb 22, 2026
Luxury Apartments by Hyatus at Pierpont
The Hill
Save 100% on your flight
Price was $1,880, price is now $1,419 per person
$1,419
per person
May 17 - May 19
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The place could have been a little cleaner I found hair in the bed and crumbs and dirt in the couch and under it as well the walls were stained and the carpet was stained in the bedroom it definitely was a big difference from the first time I stayed there
Reviewed on Feb 16, 2026
Best Western Executive Hotel Of New Haven - West Haven
Price was $494, price is now $406 per person
$406
per person
May 17 - May 19
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
everything in the hotel was amazing until the night staff arrived i went down to ask for another roll of toilet paper and he said he couldn’t go get any and told us we could use the downstairs lobby bathroom if we needed to use it
Reviewed on Feb 24, 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Save 100% on your flight
Price was $2,047, price is now $1,778 per person
$1,778
per person
May 17 - May 19
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (60 reviews)
Everything here has been excellent. I am a travel nurse and they have really helped to make my trip here the best.
Reviewed on Feb 27, 2026
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
Sheraton Hartford Hotel at Bradley Airport
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $263 total per night from Mar 14 to Mar 15
$263 total
Mar 14 - Mar 15
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Recently the restaurant was renovated, great job and the food was good. Nice upgrade!
Reviewed on Feb 26, 2026
Extended Stay America Suites Hartford Farmington
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $101 total per night from Mar 26 to Mar 27
$101 total
Mar 26 - Mar 27
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
Clean, better than expected, nice staff, quiet room and comfortable bed. Great deal for the price
Reviewed on Feb 27, 2026
Hampton Inn & Suites Hartford/Farmington
301 Colt Hwy Farmington CT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $143 total per night from Mar 21 to Mar 22
$143 total
Mar 21 - Mar 22
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Staff was very friendly. Room was spacious and clean. We had a great stay.
Reviewed on Feb 28, 2026
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.
