Discover a selection of 401 vacation rentals in Litchfield County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $226 per night, and houses and cabins are popular options for a stay in Litchfield County. Either way, you'll find a rental for everyone's needs.
Destination guide

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.

Things to 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.

Natural features

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.

How many vacation rentals are available around Litchfield County, US?

Our 2021 property listings offer a large selection of 401 vacation rentals around Litchfield County. From 309 house rentals to 47 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Litchfield County?

There are many lovely places to stay for a holiday trip or just for a weekend in Litchfield County. From Vrbo travelers, the top most popular destinations to visit are:

  • New Milford: 167 vacation rentals
  • Sharon: 126 vacation rentals
  • Salisbury: 185 vacation rentals
  • Morris: 111 vacation rentals
  • Litchfield: 140 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Litchfield County! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Litchfield County?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Litchfield County:

  • New Milford: 167 rentals
  • Sharon: 126 rentals
  • Salisbury: 185 rentals
  • Morris: 111 rentals
  • Litchfield: 140 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Litchfield County?

Vrbo offers a large selection of rentals near lovely places in Litchfield County. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Mohawk Mountain Ski Area: 220 rentals
  • Litchfield Town Green: 218 rentals
  • Lime Rock Park: 335 rentals
  • Farmington River Tubing: 140 rentals
  • Tapping Reeve House and Law School: 217 rentals

But there are many other points of interest around Litchfield County listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Litchfield County

New Milford
167 vacation rentals
126 vacation rentals
185 vacation rentals
111 vacation rentals
140 vacation rentals
100 vacation rentals
Cornwall Bridge
151 vacation rentals
154 vacation rentals
112 vacation rentals
136 vacation rentals
147 vacation rentals
99 vacation rentals
New Preston
132 vacation rentals
Falls Village
110 vacation rentals
East Canaan
72 vacation rentals
80 vacation rentals
South Kent
122 vacation rentals
Washington Depot
128 vacation rentals
109 vacation rentals
80 vacation rentals