Holiday rentals with beach access in Litchfield County

Cozy Cabin, Fireplace, Ski Nearby

Escape to Deer Ridge Cabin, a serene & cozy retreat designed to help you unwind. Relax by the warm glow of the fireplace or venture out to enjoy nearby skiing & tubing at Mohawk Mt. and Mt. Southington. Explore scenic hiking trails, indulge in local wineries, or visit Litchfield just 10 minutes away for fantastic dining & boutique shopping. Located only 2 hours from NYC, this peaceful cabin offers the perfect winter escape to nature while keeping you close to it all. Your perfect getaway awaits!

Rustic Pond Cabin: Nature, Stars & Serenity

Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom 1 bath private suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private deck. Moon or star gazing by night. We follow all Airbnb policies & State of CT cleaning guidelines. Please do not trespass on the property of private residences, across the street on the lake side. These are private residences. There are public beaches public access areas for your enjoyment.

Getaway for a weekend! Close to Ski Sundown.

Looking for a quaint and cozy little place to stay in the city of Winsted Ct.? Just relax and enjoy this one bedroom,one bath, air conditioned and fully equipped apartment. Visit surrounding breweries, State parks, West Hill and Highland Lake, fly fishing and tubing on the Farmington River, Gilson Cafe and Cinema ,Laurel Duckpin Bowling, just a few miles from Ski Sundown, close to private schools and so many great places to dine. ,if you are a smoker please don’t book the apartment.

Cozy Getaway | Pet Friendly | Amazing Location

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Retreat w 50 acre forest, waterfalls, tennis/bball

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (hike, sledding, 5 minutes from Mohawk Mtn Skiing). Hand built, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. Video: "Cornwall Hollow Teahouse" on YT or IG

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

The Ancram A - Luxury Mid-Century Modern Cabin

Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.