Winsted Vacations from $258
Book a Hotel + Flight or Car together to unlock savings
Your Winsted Vacation
The easiest way to experience this vibrant city is with a customized Winsted vacation package. Stay in the neighborhood of New Hartford, which is great for nature, history and skiing or choose someplace else — our package deals are all about you. If your trip to Winsted includes a little sightseeing, drop by major attractions such as Highland Lake, Jerram Winery and Laurel Lanes. Whoever you're going away with and whatever you plan to spend, your ultimate Winsted vacation is just clicks away with Expedia.
The Latest Winsted vacation packages
Price found within the past 48 hours. Click for updated prices.
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
Price was $417, price is now $375 per person
$375
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Clean and convienant for families . There are restaurants walking distance . Only thing was there were no microwaves in the room. Would still visit again enjoyed the pool and hot tub .
Reviewed on Jan 19, 2026
Discover the most popular places to visit in Winsted
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.
Winsted Hotel Deals
Extended Stay America Suites Hartford Farmington
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $92 total per night from Feb 8 to Feb 9
$92 total
Feb 8 - Feb 9
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
Clean although parking lot not cleaned well always enjoy staying at this facility convenient to everything in the area staff is friendly and accommodating
Reviewed on Jan 23, 2026
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 Feb 14 to Feb 15
$263 total
Feb 14 - Feb 15
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
I love this Wonderful Location and the breakfast is astounding!
Reviewed on Jan 28, 2026
Hampton Inn & Suites Hartford/Farmington
301 Colt Hwy Farmington CT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $141 total per night from Feb 7 to Feb 8
$141 total
Feb 7 - Feb 8
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
The room and common spaces/amenities were clean and modern, and the staff treated us very well!
Reviewed on Jan 24, 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 Winsted Vacation Packages
Winsted Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 7,700 |
Top Sights | Connecticut Valley Winery, Winchester Historical Society and Jerram Winery |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.