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.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
Price was CA $937, price is now CA $923 per person
CA $923
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New Haven (HVN)
8.2/10 Very Good! (622 reviews)
Everything was perfect!

Reviewed on Jul. 27, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was CA $1,103, price is now CA $1,029 per person
CA $1,029
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (423 reviews)
Everything was good

Reviewed on Jul. 25, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was CA $1,180, price is now CA $1,106 per person
CA $1,106
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,725 reviews)
It was good for the cheap price But needs updating bad and got woken up at 5 am by constant slamming doors

Reviewed on Aug. 20, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was CA $1,003, price is now CA $949 per person
CA $949
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,052 reviews)
Beds comfortable. Breakfast selection good.

Reviewed on Aug. 19, 2025

Ready to book your vacation to Winsted?

 

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Winsted Hotel Deals

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

2.5 out of 5
600 Spring St, Windsor Locks, CT
Fully refundable
The price is CA $153 per night from Sep 1 to Sep 2
CA $153
CA $175 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,117 reviews)
"Close to the airport"

Reviewed on Aug. 19, 2025

Holiday Inn Express & Suites Bradley Airport by IHG
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
16 Ella T. Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Aug 27 to Aug 28
CA $187
CA $216 total
Aug 27 - Aug 28
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Stayed here after my flight out of Hartford airport was significantly delayed. Very close tot he airport ($19 uber ride), riim rate was fair ($120 for the night, booked last minute), as were the in-room meal decries (roughly $25 with tax, tip each. Would recommend for practical traveler looking for ..."

Reviewed on Aug. 17, 2025

DoubleTree by Hilton Hartford - Bradley Airport
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd, Avon, CT
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 24 to Aug 25
CA $186
CA $244 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"very nice property. friendly and helpful staff."

Reviewed on Aug. 15, 2025

Avon Old Farms Hotel
See all 800 properties in Winsted
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Winsted vacation package cost?
Offering great value package deals from CA $923 on Expedia, you'll be pleasantly surprised at how much a vacation to Winsted costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winsted?
Travel in the off-season and you're likely to score cheap Winsted vacation packages. Bear in mind that public holidays and major festivals and events can impact prices, so do your research before you go.
How many days is enough for Winsted?
We recommend booking a Winsted vacation for at least 3 days. This will give you enough time to visit top sights such as Laurel Lanes and Platt Hill State Park, and check out neighbourhoods like Winchester and West Hill Lake. You could even slot in a day trip outside of Winsted.
Is it worth booking a vacation package to Winsted?
During your Winsted vacation, you can look forward to enjoying some top-notch nature and culture. Leave enough room in your itinerary to explore leading attractions like Highland Lake and Laurel Lanes.
How to find the best Winsted package deals?
Use Expedia's handy filters to help you find some terrific Winsted package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Winsted package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Winsted vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still have the freedom to create a tailored Winsted vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Winsted?
If you have your Winsted travel dates finalized, book as soon as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Winsted?

  1. Choose when to go: Check your schedule and get packing. Your favourite time of year and the available activities will also help you decide when to escape to Winsted.
  2. Plan your budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Winsted.
  3. Decide your trip length: Think about how much time you want to spend discovering Winsted. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Winsted vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.