Winchester Vacations from $494
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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.
La Quinta Inn & Suites by Wyndham New Haven
Long Wharf
Save 100% on your flight
Price was $650, price is now $494 per person
$494
per person
Oct 1 - Oct 5
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
6/10 (1,308 reviews)
Great place, close to everything, check in wasn’t great, felt like I was bothering checking in.
Reviewed on Jul 27, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
Save 100% on your flight
Price was $1,076, price is now $785 per person
$785
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Hyatus Luxury Residences City Crossing
The Hill
Save 100% on your flight
Price was $945, price is now $729 per person
$729
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (32 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!
Reviewed on Jul 24, 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Save 100% on your flight
Price was $927, price is now $731 per person
$731
per person
Oct 1 - Oct 5
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (85 reviews)
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived.
The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!
Reviewed on Jul 6, 2026
Stay near popular Winchester attractions
Winchester Hotel Deals
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR
Winchester CT
Sheraton Hartford Hotel at Bradley Airport
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $273 total per night from Aug 15 to Aug 16
$273 total
Aug 15 - Aug 16
Total with taxes and fees
Avon Old Farms Hotel
279 Avon Mountain Rd Avon CT
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $242 total per night from Aug 16 to Aug 17
$242 total
Aug 16 - Aug 17
Total with taxes and fees
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.