Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite

The exterior of a country home is displayed, featuring a light-colored facade with black shutters. A pathway leads to the porch, which overlooks a grassy area and open fields. A small table and chairs are visible in the yard, surrounded by lush greenery.

Home in Torrington

4.99 out of 5 average rating, 103 reviews

Country living at it's finest

Cozy country home. Quiet and serene; a great place for a get away in Litchfield County Connecticut. An ideal location ,Torrington is about 2 1/2 hours from Boston and NYC and convenient to the Berkshires. Within driving distance to various outdoor activities and attractions including hiking trails, breweries, distillery, wineries, skiing, golf antique shopping, restaurants and variety of entertainment . The hosts are accessible for directions, assistance, or a fun history lesson of the area.

Top guest favorite

Guest suite in Winsted

4.96 out of 5 average rating, 149 reviews

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom private bath suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. We follow all Airbnb policies & State of CT COVID 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.

Guest favorite

Tiny home in New Hartford

4.91 out of 5 average rating, 53 reviews

West Hill Outpost

Follow us | @westhillcabin Escape the hustle and bustle of the city and unwind at the Outpost, a tiny home nestled on an acre of serene landscape just off West Hill Lake. A few hours’ drive from NYC & Boston, the home offers the perfect retreat for a relaxing getaway with a friend or family. Offering a cozy wood stove for chilly evenings, or central AC in the summer for comfort. The well-equipped kitchen is efficient. The space features a streaming-ready TV, fast Wifi, and a Murphy Wall Bed!

Guest favorite

The interior space features wooden walls and a warm wooden floor, creating a cozy atmosphere. A large dining table is surrounded by black chairs, while a spiral staircase ascends to the upper level. Natural light floods the room through a skylight and a window.

Home in Winsted

4.96 out of 5 average rating, 27 reviews

Newly renovated lakefront home!

Welcome to this newly renovated, freshly decorated, cozy waterfront retreat with breathtaking views of the lake! Nestled in the desirable 2nd Bay on West Wakefield Blvd you’ll find this beautifully remodeled 900 square foot lakefront home with 4 bedrooms and 2 full bathrooms. You will enjoy beautiful views from both indoor and outdoor living spaces featuring 50 feet of direct waterfront access for fishing, boating, and swimming, and ample off-street parking. Comfortably sleeps 8-9 guests!

Guest favorite

A cottage is nestled among lush greenery, showcasing a blend of wildflowers and dense foliage. The light-colored exterior features large windows offering a view of the surroundings. An artistic representation of a heron stands among the garden, contributing to the tranquil setting.

Cottage in Winsted

4.9 out of 5 average rating, 41 reviews

Cottage Ease.

Take it easy at this unique and tranquil getaway. Welcome to Highland lake. Enjoy the serenity of the mountains and the lake. Surrounded by trails for biking and hiking. Highland lake offers a Marina you can rent a boat or kayak for the day. Close to Litchfield center for unique shopping and eating. Or you can shut it all off and just watch the Eagles and the Heron fly over the lake. Come and enjoy the uniqeness of this cottage nestled into the side of a rock formation with beautiful views.

Top guest favorite

A winter scene is depicted with a red building contrasting against a vibrant sunset sky, filled with shades of orange and pink. Snow covers the ground and rooftops. Dark trees frame the image, contributing to the serene atmosphere.

Apartment in Canaan

4.99 out of 5 average rating, 144 reviews

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 brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Guest favorite

An open living area showcases high wooden ceilings with skylights, allowing natural light to fill the space. A simple seating arrangement includes a dark sofa and stylish chairs, while a light rug anchors a coffee table. Modern decor complements the neutral color palette.

Vacation home in Torrington

4.95 out of 5 average rating, 213 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Top guest favorite

A serene garden area is visible, featuring large trees providing shade. A stone bench is positioned near a Koi pond surrounded by lush greenery and blooming flowers. Additional seating can be seen in the background, offering a peaceful spot for relaxation.

Apartment in Torrington

4.98 out of 5 average rating, 167 reviews

Apartment on Main St.

Hidden gem. Large combined living room/bedroom apt with separate kitchen and balcony. Private entrance. This is 1 unit in a 3 family house. 10 to 15 minutes walking distance to downtown shops, restaurants, Warner Theatre and Nutmeg Ballet. Shared huge garden, with Koi pond and pergola. Parking in the driveway for 1 car (possibly more, message for details). WiFi and Smart TV with some local channels (no cable). 45 minutes to Bradley Airport, 2 hours to NYC, 20 minutes to ski slopes.

Top guest favorite

A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.

Treehouse in Wallkill

4.99 out of 5 average rating, 315 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Guest favorite

The entrance features a welcoming front porch with a wooden railing and a mat that reads 'HOME.' A white door is highlighted by a decorative light, and greenery is visible in the background, creating a fresh and inviting atmosphere.

Apartment in Winsted

4.93 out of 5 average rating, 91 reviews

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. ,

Top guest favorite

The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.

Guesthouse in Granby

4.99 out of 5 average rating, 823 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Guest favorite

Cottage in Granby

4.89 out of 5 average rating, 199 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.