Winsted holiday lettings

We found 75 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Winsted that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Choose a holiday rental for your Winsted getaway

Learn about the unique charm of Winsted with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Winsted

Are you looking for attractions to see during your stay? Venture out of your holiday home and experience everything that makes Winsted a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Sundown (6.6 mi / 10.6 km)
  • Connecticut Valley Winery (6.9 mi / 11.1 km)
  • Flamig Farm (10.7 mi / 17.2 km)
  • Sunset Meadow Vineyards (11.8 mi / 18.9 km)
  • Lost Acres Vineyard (12.1 mi / 19.4 km)
  • Miranda Vineyard (12.5 mi / 20.2 km)

Exploring the natural features in Winsted

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winsted is a great place to get outside. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Highland Lake (2.2 mi / 3.5 km)
  • Satan's Kingdom State Recreation Area (6.8 mi / 11 km)
  • Enders State Forest (9.6 mi / 15.5 km)
  • Mill Pond Park (10 mi / 16.1 km)
  • Harwinton Conservation and Recreation Area (10.4 mi / 16.8 km)
  • Buckingham Road Recreation Area (11.9 mi / 19.2 km)

Transport to and around Winsted

The nearest airport is in Hartford, CT (BDL-Bradley Intl.), located 19.3 mi (31 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Westfield, MA (BAF-Barnes Municipal), which is 24.5 mi (39.4 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Winsted?
Houses are the most popular kind of holiday rental in Winsted, according to our data. Even if you've got a different idea in mind, Vrbo has properties in a variety of sizes and shapes. Look over our options to find your perfect match.
How much does it cost to rent a holiday rental in Winsted?
Length of stay, property type and season are some of the things that can determine the price of a holiday home. Simply click on your dates of travel to find your ideal match. From comfy cabins to sprawling luxury villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Winsted?
The average price for a holiday rental near the beach in Winsted depends on when you're travelling and the size and type of property you're searching for. Find prices quickly and easily on Vrbo by entering your destination and travel dates. Then use our handy filter tool to pick the number of bedrooms and amenities that you require, like WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday rentals in Winsted?
Yes, there are. You'll have a choice of eight holiday homes that roll out the welcome mat in Winsted on Vrbo. Our cuddly best friends also deserve a getaway, so simply use our search function for pet-friendly holiday rentals to book a perfect pad where your puppy can get in on the fun.
What are popular rental amenities in Winsted?
Some of the most popular rental amenities people search for in Winsted are a garden, a lake view and a barbecue grill. Whether you're on a trip with family, pals or even pets, Vrbo holiday homes feature the best amenities for starting a new adventure with the people you cherish the most.
Are there large group holiday rentals in Winsted?
Take your pick of six Vrbo properties in Winsted that can sleep five or more people. You'll get all the privacy and space you need to relax with your favourite people — and nobody else.
Are there holiday rentals in Winsted that welcome kids?
Gather your entire family for an epic adventure in Winsted at one of our eight family-friendly holiday homes. These stays offer conveniences that are ideal for trips with youngsters, including laundries, living rooms and pools. Just check the "Properties good for families" filter box and select your favourite.
What are the top attractions for families in Winsted?
Keeping the kids occupied during your holiday in Winsted is a snap with these fabulous family-friendly attractions:

  • Winchester Historical Society
  • Laurel Lanes
  • Highland Lake

Can I find two-bedroom holiday rentals in Winsted?
Winsted has three two-bedroom properties for you to pick from. Go for a holiday home with all the space and privacy you're looking for at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Winsted?
You'll have a choice of six holiday rentals with WiFi in Winsted. If you'd like to disconnect from daily life while on holiday, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Winsted?
Winsted has eight holiday rentals where you'll be able to kick back in air-conditioned comfort. To book a property on Vrbo featuring this perk, enter your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Winsted?
You'll need to check with the Winsted holiday property you're considering on Vrbo as the minimum age varies. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental in Winsted for?
It's up to the Winsted property. To view a list of options offering extended stays, just enter your travel dates and number of guests into Vrbo. Enjoy having the place to yourself, along with home comforts such as air conditioning, a kitchen and outdoor spaces to play in. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

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