Litchfield County vacation rentals

We found 755 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
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Select from 266 homes, 65 cottages, and other vacation rentals in Litchfield County to find one that's perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll have the amenities you expect and more, which might include air conditioning and a pool. You're sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Litchfield County: a posh getaway if you need to escape Manhattan

It's a common notion that Manhattanites drive up to the Hamptons for the weekend. After all, that's what pop culture has been feeding us all this time, right? But apparently, there's an alternative getaway for when city folk feel like the Hamptons are too buzzy for a quiet weekend. Instead, they drive up to their nests in Litchfield County, a lush pocket of rolling hills in the northwestern corner of Connecticut. Staying at Litchfield County vacation rentals lets you escape the city in the way that urban types do.

Fall in love with picture-perfect Lake Waramaug

Litchfield County has no lack of Instagram-worthy sights, but few can ever compare to the serenity of Lake Waramaug. With the mirror-like sheen of its waters, the lush greenery on its shores, and the lack of real estate development surrounding it, Lake Waramaug makes an awesome background for a selfie, but try to take pics of just the views too. The lake is the focal point of Lake Waramaug State Park, where you can swim, fish, go canoeing, or enjoy a picnic. The state park is the only public access to the lake.

Time slows down in Litchfield County

Perhaps one of the reasons why urbanites make the drive up to Litchfield County on weekends is time seems to move much more slowly there, compared to the frenetic way it seems to flow in the city. In Litchfield County, you can breathe deeply and savor each breath as you meditate your stress away in the comfort of your Litchfield County vacation rental. You can reconnect with nature by hiking the 5-mile segment of the Appalachian Trail that cuts through the county. Or you can shop for unique goods, handicrafts, or gorgeous antiques.

Litchfield County is glorious in fall

Litchfield County experiences 4 seasons, and each season has its own character. Winter draws in cross-country skiers and vacation merrymakers, while spring is for whitewater canoeing. Summer brings in the long-distance hikers who want to pit themselves against the rigors of the Appalachian Trail. Fall, however, is when Litchfield County becomes truly breathtaking, when the green of the countryside turns into different shades of burning orange and red. Fall is also one of the busiest times for Litchfield County vacation rentals, so make sure you book yours way ahead.

The hills are alive and teeming with charm

With a total area of 945 square miles, Litchfield County is the largest county in Connecticut. Yet with a population of only 183,000 souls, it's Connecticut's least dense area. Though generally flat with few points of elevation, Litchfield County has a hilly side aptly known as Litchfield Hills, an area occupied mostly by picturesque farms that have been run by the same families for generations, some dating back to the late 1700s. Litchfield contains a portion of the Appalachian Trail, considered to be one of the most challenging long-distance hiking trails in the world.

Frequently asked questions

What is the best area to stay in Litchfield County when booking a vacation rental?

New Milford is among the most in-demand areas to select a vacation property in Litchfield County. Looking for some cool things to do here? Be sure to check out Elephants Trunk Flea Market and Lovers Leap State Park.

What is the most popular type of vacation rental accommodation in Litchfield County?

Houses are the most popular kind of vacation rental in Litchfield County, according to our data. Even if you have something else in mind, Vrbo has properties in many shapes and sizes. Look through our options to find your ideal fit.

How much does it cost to rent a vacation rental in Litchfield County?

The average price for a vacation home in Litchfield County is determined by a number of factors, such as season, property type and length of stay. Whether you prefer a sprawling house with room for friends and family or a cozy cottage just for the two of you, just add your dates of travel to see some great-value stays.

How much does it cost to rent a beach house in Litchfield County?

When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Litchfield County travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the features and amenities you want.

What are popular rental amenities in Litchfield County?

Off-street parking options, a fridge and a microwave oven head the list of most popular rental amenities in Litchfield County. Whether you're taking to the road alone, with your spouse or as a family, Vrbo will help you find a vacation rental that matches your style with all the features you're looking for.

Are there large group vacation rentals in Litchfield County?

There are 53 properties in Litchfield County that can sleep 10 or more people. Whether you're planning time away with the family or an event like a birthday party, there's ample room to get your loved ones together under the same roof.

What are the top attractions for families in Litchfield County?

Keep the kids occupied at these fun family-friendly attractions in Litchfield County:

  • Satans Kingdom State Recreation Area
  • Lake Waramaug State Park
  • Elephants Trunk Flea Market

Can I find two-bedroom vacation rentals in Litchfield County?

You can select from 52 two-bedroom rentals in Litchfield County. Settle the kids into the second room or maybe fill it with a couple of your best friends. There's space for whoever's fortunate enough to be joining your journey.

Are there vacation rentals with WiFi in Litchfield County?

Whether you want to keep up to date with the news, reply to emails or surf social media, there are 126 vacation homes with WiFi in Litchfield County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

How old do you have to be to rent a vacation rental in Litchfield County?

The minimum age requirements can vary across properties on Vrbo, so look at the rules of the vacation rental in Litchfield County you want. But usually, it's 16, 18 or 21.

How long can I rent a vacation rental in Litchfield County for?

It's really down to the Litchfield County property. To view a list of options offering extended stays, just enter your dates and guest number into Vrbo's search page. Enjoy having the entire place to yourself, along with home comforts such as a kitchen, air conditioning and a backyard where the kids can burn off energy. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

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