Winsted Vacation Packages
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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.
Top Winsted Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $1,383, price is now CA $957 per person
CA $957
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean.
Reviewed on May 17, 2026
Head of Pond House
Price was CA $3,985, price is now CA $3,270 per person
CA $3,270
per person
Jun 18 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (5 reviews)
Very special property. One of my favorites. Beautiful, exceptionally clean and in a gorgeous location. Host was exceptional and communication excellent.
Reviewed on May 9, 2026
The Scranton Seahorse Inn
Madison Center
Price was CA $2,011, price is now CA $1,785 per person
CA $1,785
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9/10 Wonderful! (242 reviews)
We had a wonderful stay. Perfect location, great staff, and check-in process, and our room was delightful.
Reviewed on Apr 22, 2026
Saybrook Point Resort & Marina
Old Saybrook Center
Price was CA $2,861, price is now CA $2,550 per person
CA $2,550
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (1,001 reviews)
We ended up getting an upgrade into one of the two bedroom two bathroom pillows due to the renovation on the main hotel. We were pleasantly surprised we felt like we were home. It was so nice so relaxing. Everything was amazing and we could literally walk right across the street to get something to eat at fresh salt or at the choo-choo lounge views of the water at home field by having a full kitchen and laundry felt like a great little mini vacation we’ve been there before and we will be back again. Bravo.
Reviewed on May 17, 2026
Winsted Hotel Deals
The Farmington Inn & Suites
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from May 20 to May 21
CA $191
CA $243 total
May 20 - May 21
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"I really enjoyed my stay at the hotel. I especially liked the large spacious room. It was a pleasant surprise."
Reviewed on May 18, 2026
Sheraton Hartford Hotel at Bradley Airport
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
The price is CA $361 per night from May 24 to May 25
CA $361
CA $416 total
May 24 - May 25
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Very convenient to airport when you have an early flight to catch. Parking safe and easy as well."
Reviewed on May 18, 2026
Hampton Inn & Suites Hartford/Farmington
301 Colt Hwy Farmington CT
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Jun 2 to Jun 3
CA $186
CA $214 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Our stay was lovely. The room was very clean. The staff was very accommodating. My only question is why the handicap parking is so far away from the entrance."
Reviewed on May 18, 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.
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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.
