Vacation rentals in Lakeville

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

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

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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.

Stay in Downtown Canaan

This light-filled space with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. WELL BEHAVED dogs are welcome. Poop bags are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK to see what our area offers!!!

Charming 4b farmhouse group getaway - Hike, Relax

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

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.

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town , pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

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.

The Studio

Millerton, NY is a weekenders dream! Enjoy a peaceful stay at our newly renovated Studio fully furnished and with a Queen Bed. You’re just a short walk from everything the village of Millerton has to offer! Grab a bite to eat at the popular Oakhurst Diner or indulge in a coffee at Irving Farm Coffee Roasters. After that, make your way to Westerlind to do a little shopping, pop into Oblong Books or enjoy the charm of an old time film theater by checking out The Movie house.

Lakeville Studio, 1st floor Near Lake, Limerock,AT

Cozy convenience in the center of Lakeville! Short walk to convenience store, several restaurants, a nail salon, gym and package store. There is a laundromat nearby as well. 1/2 mile to Lake Wonoscopomuc, nearby park and tennis courts, and beautiful walks on rural roads. Very close to local boarding schools and Limerock Racetrack. There are 2 units in this building- this listing is the downstairs only, there is a shared entrance, but units are separate of each other.