Apartment holiday rentals in Litchfield County

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Litchfield Hills Hideaway

Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full kitchen, living room, bedroom with queen bed, and full en suite bathroom. WiFi and cable TV included. All located less than 2 miles from historic Litchfield Center. Our property borders on the White Memorial Foundation nature preserve, with over 40 miles of hiking trails. Mohawk Mountain Ski area in Cornwall and Ski Sundown in New Hartford are only a short drive away.

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

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.

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

The Litchfield Nook - Cozy Uptown Apartment

Welcome to a cozy and peaceful nook in the hills! This well appointed apartment provides a home away from home feel. The unit is located on the first floor of a multi unit family house and sleeps 4 comfortably. You will be within walking distance to the iconic Litchfield Green and White Memorial Foundation. Everything that there is to see and do in Litchfield is within a short driving distance. Enjoy the beauty of Litchfield and come join us as our guest!

Cozy Apartment with Water View of Brook

Lower Level Beautiful Space: Well kept with an amazing view of a Beautiful Brook that Runs through the Backyard. It is a small cottage style home and you will have the best views of the Brook. You will also hear and see the Brook from the Bedroom, Kitchenette and Patio. Depending on the season it will Vary. If you have 2 Cars please make sure you let me know so I can accommodate.

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

The Village Apt

Bright apartment overlooking the historic Litchfield Green. Housed above the popular Village Restaurant in the center of town. Walking distances to fine restaurants, shopping, antique shops and jewelry stores. Close proximity to local vineyards, hiking trails, the famous White Flower Farm.