Litchfield County Vacation Rentals
Explore Red Cottage’s collection of Litchfield County vacation rental homes and cottages, an easy drive from New York City in Connecticut’s scenic northwest corner. With rolling hills, quiet backroads, and classic New England charm, Litchfield is a destination made for stepping away from the noise and settling into a slower, more restorative pace.
From waterfall walks and lake days to small towns like Kent, Washington Depot, and New Preston for cafes, shops, and easy dinners, Litchfield County offers a simple mix of nature and discovery. Plan fall weekends around foliage drives and crisp hikes, spend summer afternoons on the water, or lean into winter with cozy stays, snowy trails, and a day of skiing nearby before coming home to relaxed evenings back at your Red Cottage stay.
What Our Guests Are Saying About Their Litchfield County Stay
“An absolutely wonderful stay. The house was beautiful, well equipped and very conveniently located close to Mohawk Mountain! We would love to return again soon!”
“Beautiful area, amazing home! Great for kids. Would love to come back here! Hosts were very helpful!”
“We had such a lovely stay. The house is beautiful and was perfect for a winter ski weekend for our family. The host thought of everything we could possibly need; including lots of firewood and board games. It was super convenient to Mohawk and we will definitely be back!”
“Extremely convenient for skiing at Mohawk, excellent for kids, a lovely house altogether!”
“Our stay felt like we were at home. For the first time in 8 years, we were able to celebrated Thanksgiving with our beloved daughter and her partner and her family. This was the place both families met and created lasting bonds. We created memories that will last forever.”
“We spent Thanksgiving weekend at this Cornwall home and absolutely loved it. The kitchen was equipped beyond our expectations, and there were plenty of extra linens and pillows in the closets. The whole place was so cozyโwe felt right at home all weekend. Highly recommend! We would love to be back :)”
Experience Litchfield County
Tucked into the northwest corner of Connecticut, Litchfield County is the kind of New England escape that feels a world away without the long travel day. Think winding backroads, historic villages, lakes and waterfalls, and cozy places to linger over a great meal before heading back to your Red Cottage rental for a quiet night in.

Start with Kent Falls State Park, one of the region’s most scenic waterfall stops and a favorite any season, especially in spring and during peak fall color. For lake views, Lake Waramaug is a classic with calm water, scenic shoreline, and that instant getaway feeling.

Litchfield County’s cultural scene feels intimate and curated, with experiences that are easy to build into a weekend. Catch a live show at Infinity Music Hall for a relaxed night out. In summer, the Norfolk Chamber Music Festival is a signature experience that pairs beautifully with a countryside stay. For something unique and memorable, the American Mural Project in Winsted is worth planning around.

Let your itinerary stay flexible, and town hop at your own pace. Litchfield has a classic village feel with historic charm and an easy rhythm for strolling. Kent is a go-to for cafes, small shops, and quick access to trails. Washington Depot is ideal for browsing and a relaxed afternoon, and New Preston is perfect for a wander, a snack, and a scenic drive in between.

When you want the full outdoors reset, explore the Connecticut stretch of the Appalachian Trail, with scenic sections near Kent and Salisbury. For a peak-bagging moment, Bear Mountain is the tallest point in Connecticut and rewards you with wide, satisfying views that feel like a true escape.

A Litchfield County weekend is also easy to build around what you want to sip. Spend an afternoon at Kent Falls Brewing Company for a laid-back tasting in a countryside setting. For spirits, book a tour and tasting at Litchfield Distillery and turn it into an easy, scenic outing. If wine is the plan, Hopkins Vineyard pairs vineyard views with the Lake Waramaug area, and Sunset Meadow Vineyards in Goshen is another great stop for a relaxed tasting room afternoon.

When the temperatures drop, this region shines in a quieter, cozier way. Think snowy walks, warm drinks, and early nights in. For skiing and riding, Mohawk Mountain is the classic local option for a day on the slopes followed by a calm evening back at your Red Cottage stay.

Meals here feel like part of the trip. For a special night out, Arethusa al tavolo in Bantam is a destination worthy reservation. For a polished dinner with a great bar program, Community Table is a favorite in the Washington Depot and New Preston area. For a classic pub atmosphere with real local character, The White Horse in New Preston is an iconic stop.
Litchfield County, Season by Season
Litchfield County offers something special in every season, and the best time to visit depends on your plans. Use the guide below to compare typical weather, crowd levels, and nightly rates by month so you can choose the ideal time for hiking, small town exploring, lake days, cozy fall weekends, and winter ski getaways.
| Month | Typical Weather | Avg Temp (F) | Crowd Level | Nightly Rates | Best For… |
|---|---|---|---|---|---|
| January | Cold, snowy stretches, cozy winter weekends | 17-33 | Medium-High | $$-$$$ | Skiing at Mohawk Mountain, snowshoe walks, fireside nights |
| February | Cold, peak winter feel | 18-35 | Medium-High | $$-$$$ | Winter hikes, after ski dinners, quiet lake views |
| March | Chilly, late winter mix, early thaw | 27-45 | Medium | $$ | Shoulder-season value, early spring trail walks, cozy town days |
| April | Cool, bright spring, waterfalls pick up | 36-58 | Low | $ | Kent Falls, uncrowded hikes, scenic drives, reset weekends |
| May | Mild, fresh green season | 46-69 | Medium | $$ | Lake Waramaug days, farms and gardens |
| June | Warm, early summer | 55-78 | Medium-High | $$$ | Lake time, longer hikes, brewery and vineyard afternoons |
| July | Warm, peak summer weekends | 60-83 | High | $$$$ | Full summer getaways, swimming and boating, family trips |
| August | Warm, late summer, long evenings | 58-81 | High | $$$$ | Outdoor adventures, town hopping, relaxed lake days |
| September | Pleasant, cooler nights | 51-74 | Medium-High | $$$ | Prime hiking weather, early foliage hints, farm stands |
| October | Crisp, peak fall color season | 40-62 | Very High | $$$$ | Foliage drives, cozy weekend stays |
| November | Cool, quiet off-season | 31-50 | Low | $ | Slow weekends, fireside cooking nights |
| December | Cold, early snow possible, holiday feel | 22-38 | Medium-High | $$-$$$ | Holiday escapes, winter reset weekends, festive small towns |
Frequently Asked Questions
Litchfield County is an easy drive from New York City. Popular bases include Litchfield at about 2 hours from Manhattan.
Minimum stays vary by home & season. Most properties have a two night minimum, with longer minimums during peak dates and holidays.
Yes. Many Red Cottage homes are close to Litchfield County’s best spots, so it’s easy to mix a waterfall hike like Kent Falls, a lake day at Waramaug, and a cozy town stop in Kent, Washington Depot, New Preston, or Litchfield.
Keep it simple and let the area set the pace. Choose one outdoor highlight like Kent Falls, Lake Waramaug, or a scenic Appalachian Trail section near Kent or Salisbury, then pair it with one town to explore such as Kent, Washington Depot, New Preston, or Litchfield for cafes, browsing, and an easy dinner. Build in time for a backroad drive and a relaxed evening at your Red Cottage home, since Litchfield is best enjoyed when it feels unhurried.
It depends on what you want to do. Fall is peak for foliage, scenic drives, and crisp hiking weather. Summer is ideal for lake days and outdoor dining. Winter is perfect for ski weekends and cozy nights in. Spring is quieter, with fresh green trails and easier reservations.