Winsted Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Winsted

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 S$174 per night from 25 Aug to 26 Aug
S$174
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (1,105 reviews)
Basketball HOF
"Because of the rain cable was in and out and telephone didn’t work in the room."

Reviewed on 3 Aug, 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 S$199 per night from 16 Aug to 17 Aug
S$199
16 Aug - 17 Aug
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Great customer service!"

Reviewed on 2 Aug, 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 S$186 per night from 17 Aug to 18 Aug
S$186
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Great place stayed there 6 days in July."

Reviewed on 5 Aug, 2025

The Farmington Inn & Suites
See all 805 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 holiday package cost?
You can snap up a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday 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 holiday, we recommend staying for 3 days. Divide your time between discovering Winchester Historical Society, Highland Lake and other top attractions, in addition to exploring neighbourhoods like Winchester and West Hill Lake. If you've got some spare time, add a day trip or tour to your Winsted holiday itinerary.
Is it worth booking a holiday package to Winsted?
During your Winsted holiday, 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 holiday package well in advance.
Is it cheaper to book a Winsted holiday as a package?
Expedia holiday 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 personalised Winsted holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.