Holiday houses in Lakeville

Peace at Last

Vacation or work remotely at this unique & tranquil property. Charming & cozy historic late 1800's post & beam 2 1/2 bedroom home with rustic and vintage elements; claw foot tub, private master bedroom. Enjoy garden: flower herb & fruits, sounds of nature & brook Only 2 hrs from NYC & Boston Ski, Hike, Swim, Bike, Horseback ride, Zipline, Tour private schools, historical & music sites, Tanglewood, Limerock Race Track, Appalachian Trail, Ski Jump Fest! 2-3 mainly outdoor & easy cats to feed

Family · Value · Wi-Fi

Lakeville studio, 2nd floor Near Lake, Limerock AT

Spacious second floor studio. Close to local private schools, Catamount and Butternut ski areas, Limerock park, nearby Berkshires attractions, ski jumps! Short walk to convenience store, several restaurants, a nail salon, gym and package store. There is a laundromat nearby. 1/2 mile to Lake Wonoscopomuc, nearby park and tennis courts, and beautiful walks on rural roads. There are 2 units in this building- this listing is the upstairs, shared entrance but units are separate of each other. Edit

Value · Family · Air conditioning

Lakeville Lodge with Private Pool

Welcome to Lakeville Lodge – a rare-find Connecticut retreat for families & couples conveniently nestled in the foothills of the Berkshires. Lounge by the private pool, unwind by the fire, or walk down the street for an action-packed day at Lakeville Lake. With the rail trail at your door and favorites like Fern and the White Hart Inn just a short walk away, our lodge is the perfect place to call home. 5min to Hotchkiss 7min to Salisbury 25min to Berkshire School 30min to Great Barrington

Family · Location · Accuracy

Under Mountain House

Our home is designed to be your home away from home! It has been newly renovated with comfort in mind so you can enjoy your stay in the Berkshires. Whether you are here to hike parts of the Appalachian Trail, stroll into town for a leisurely meal, enjoy Lime Rock Race Track or explore the many surrounding New England towns you can be assured you will always have a comfortable home to come back to!! My home is located just a 3 minute walk to the center of town and the historic White Hart.

Location · Family · Indoor spaces

Charming and relaxing 4b farmhouse group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining

Location · Family · Layout

Woodland A-Frame

Our A-frame home stands out for the way it invites the outdoors in. With skylights and soaring windows, you can experience the natural beauty of the forest from every room—whether you're sipping coffee while watching deer or wild turkeys wander through the yard, enjoying the gentle drift of autumn leaves, or cozying up during a summer storm. Even on chilly days, the house feels connected to nature in a peaceful, grounding way. Guests have access to our local swimming hole, Mudge Pond.

Location · Family · Hiking

Close to Lake/Skiing/Hiking with Picturesque Views

Classic New England Cottage on 3 acres in the Connecticut countryside on a rambling street just minutes from Lakeville, Salisbury and Millerton town centers. Only 2 hours from Boston or NYC. So many reasons to visit: ski Butternut or Catamount, hike the Appalachian Trail, swim at the Grove, bike the rail trail. Tour private schools. Take in Tanglewood, or spend time at Limerock Race Track. You are minutes away from the annual Ski Jump Festival. Pond and ridge line views.

Value · Family · Beach

The Cottage at Great Falls Luxury Getaway.

Spectacular artisan designed cottage on the banks of the beautiful Housatonic river. Located on a quiet residential cul de sac , no through traffic. Interior features plaster throughout, stone veneer and mosaic flooring and original artwork. Fully equipped kitchen, elegant dining room. Oversized soaking tub in master bath. 2 bedrooms, sleeps 4. Fabulous water and mountain views . Large outdoor deck overlooking the water, second small stone dining deck. wonderful gardens.

Location · Value · Wi-Fi

The Studio

Millerton, NY is a weekender's dream! Enjoy a peaceful stay in our newly renovated studio, fully furnished with a queen bed and private entrance. You're just a short walk from everything the village has to offer—from breakfast at Oakhurst Diner and coffee at Irving Farm to shopping at Westerlind, browsing Oblong Books, or catching a film at The Moviehouse. We also offer simple, transparent pricing with no cleaning fee. Perfect for a relaxing Hudson Valley getaway.

Family · Value · Outdoor spaces

Bright & Airy Guest Suite

Relax and unwind in this bright, stylish guest suite surrounded by mature oaks in picturesque Salisbury, CT. Located steps from the popular Undermountain trailhead and about an hour's hike to the Appalachian Trail. Short drive to Hotchkiss, Salisbury School, Berkshire School, Lime Rock, fine dining & events venues in Salisbury and Lakeville, and the chic downtowns of Great Barrington, MA, and Millerton, NY.

Family · Location · Cleanliness

The House in a Beautiful Small Upstate Town

This is a house to enjoy with the family with a lot of space and many activities, in a small town but with a lot of tourism. You can visit the town which it has a small cinema, and Rail trail for walking or biking, and it has many restaurants nearby. This house includes a living room, kitchen, 4 bedrooms, 3 full bathrooms, deck, and a big backyard. You can also do BBQ s outside.

Value · Location · Indoor spaces

“Magical” Brookside Cottage

Enjoy the serenity of our peaceful and centrally-located "Brookside Cottage". Surrounded by nature and the sounds of water, yet conveniently located less than 1 mile from everything Salisbury/Lakeville have to offer. A 25 minute drive puts you in Great Barrington, the heart of the Berkshires. Nature, music, shopping and great food await those who visit.

Family · Location · Hiking