Winsted Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winsted Vacation Packages

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 ￥17,372 per night from Aug 18 to Aug 19
￥17,372
￥19,978 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,106 reviews)
Basketball HOF
"Because of the rain cable was in and out and telephone didn’t work in the room."

Reviewed on Aug 3, 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 ￥19,897 per night from Aug 15 to Aug 16
￥19,897
￥22,881 total
Aug 15 - Aug 16
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Great customer service!"

Reviewed on Aug 2, 2025

DoubleTree by Hilton Hartford - Bradley Airport
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
The price is ￥15,574 per night from Aug 17 to Aug 18
￥15,574
￥20,450 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"all was excellent"

Reviewed on Aug 6, 2025

The Farmington Inn & Suites
See all 803 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.

Frequently asked questions

How much does a Winsted vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Winsted costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Winsted?
The off-season is the best time to travel to Winsted if you're on a budget. Another tip for getting cheap Winsted vacation packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Winsted?
To get the most out of a Winsted vacation, we recommend staying for 3 days. Divide your time between discovering Winchester Historical Society, Highland Lake and other top attractions, in addition to exploring neighborhoods like Winchester and West Hill Lake. If you've got some spare time, add a day trip or tour to your Winsted vacation itinerary.
Is it worth booking a vacation package to Winsted?
During your Winsted vacation, you can count on experiencing some top-notch nature and culture. Leave enough time in your itinerary to discover 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 fabulous 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're looking to save, plan your escape for midweek, or search for Winsted package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Winsted vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Winsted vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winsted?
If you have your Winsted travel dates confirmed, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Winsted?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to escape to Winsted.
  2. Set a budget: Consider costs like flights, meals and transportation when working out how much to set aside for your trip to Winsted. Then, select a hotel that works with your budget, whether that's an affordable option or a high-end getaway.
  3. Set the duration of your trip: Start by making a list of all the attractions you'd like to experience in Winsted. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose 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.