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.

Can I find a vacation rental around Litchfield County?

Yes, our 2019 property listings offer a large selection of 433 vacation rentals near Litchfield County. From 285 Houses to 66 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Litchfield County for a holiday or a weekend are on HomeAway.

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 HomeAway travelers, the most popular destinations to visit are:

  • Litchfield: 169 vacation rentals
  • New Milford: 184 vacation rentals
  • Lakeville: 23 vacation rentals
  • Bantam Lake: 112 vacation rentals
  • Kent: 179 vacation rentals

And HomeAway 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:

  • Litchfield: 169 rentals
  • New Milford: 184 rentals
  • Kent: 179 rentals
  • Sharon: 151 rentals
  • Washington: 174 rentals

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

Can I find easy-access vacation rentals when traveling by plane to Litchfield County?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Litchfield County are:

  • Hudson, NY (HCC-Columbia County): 529 vacation rentals
  • Bradley International Airport (BDL): 81 vacation rentals
  • Great Barrington, MA (GBR-Walter J. Koladza): 698 vacation rentals

For other airports, 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?

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

  • Lake Waramaug State Park: 289 rentals
  • Mohawk Mountain Ski Area: 264 rentals
  • Holley-Williams House Museum: 455 rentals
  • Litchfield Town Green: 224 rentals
  • Connecticut Valley Winery: 177 rentals

But there are many other points of interest around Litchfield County listed on HomeAway 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

169 vacation rentals
New Milford
184 vacation rentals
179 vacation rentals
151 vacation rentals
174 vacation rentals
244 vacation rentals
136 vacation rentals
New Preston
160 vacation rentals
125 vacation rentals
93 vacation rentals
173 vacation rentals
148 vacation rentals
57 vacation rentals
29 vacation rentals
110 vacation rentals
84 vacation rentals
154 vacation rentals
Falls Village
146 vacation rentals
New Hartford
63 vacation rentals
West Hill Lake
28 vacation rentals