Holiday houses in Winsted, Winchester

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Top-rated holiday rentals in Winsted, Winchester

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Top Guest favourite

Home in Torrington

4.99 out of 5 average rating, 102 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 favourite

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 favourite

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 favourite

Cottage in Winsted

4.9 out of 5 average rating, 40 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.

Guest favourite

Holiday home in Torrington

4.95 out of 5 average rating, 212 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.

Guest favourite

Home in Barkhamsted

4.94 out of 5 average rating, 35 reviews

2BR Family friendly home in Riverton paradise

Relax and play at this family-friendly home. In Historic Riverton Village: A 4-minute stroll to The Riverton General Store and everything else our charming village has to offer. In the heart of Outdoor Mecca: Sitting on the Farmington River and nestled between two state forests with immediate access to world-class fly fishing, cycling heaven, hiking, paddling, skiing, snowshoeing, and more. Family friendly: outfitted and baby proofed for infants and toddlers (big kids welcome too!).

Top Guest favourite

Apartment in Torrington

4.98 out of 5 average rating, 166 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.

Guest favourite

Apartment in Winsted

4.93 out of 5 average rating, 90 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 favourite

Apartment in New Britain

4.95 out of 5 average rating, 193 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top Guest favourite

Guesthouse in Granby

4.99 out of 5 average rating, 821 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 favourite

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.

Superhost

Apartment in Winsted

4.88 out of 5 average rating, 104 reviews

Haven at Highland lake

Kick back and relax in this calm, stylish space. This studio apartment offers fast internet, TV , a comfortable couch , a stylish new bathroom, a lovely kitchenette, as well as black out curtains in the bedroom. And a cozy warm fireplace. This apartment comfortably sleeps 1 adult or a couple. The couch folds out into a bed and there is bedding in a tote stored Under the bed.

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Other great holiday rentals in Winsted, Winchester

Guest favourite

Home in Barkhamsted

5 out of 5 average rating, 8 reviews

Woodland Sanctuary-hot tub|fireplace|hikes|fishing

JananiRating, 5 stars2 weeks ago

Had a great and relaxing weekend! The pups loved it. My favorite thing about this house was that the host was incredibly kind and responded super quick! The house was really clean and basically had all essential items you could need for a quick getaway. :D

Guest suite in Litchfield

5 out of 5 average rating, 5 reviews

Hemlock Hill Suite

JulieRating, 5 starstoday

A beautifully designed space, spotless, serene, quiet, relaxing. I didn't get to hang out on the back patio, unfortunately, but the grounds are lovely and I hope to return when I have more time for hanging out. Highly recommend staying here.

Top Guest favourite

Loft in Torrington

5 out of 5 average rating, 6 reviews

Modern loft in converted factory

DavidRating, 5 stars6 months ago

Exceeded expectations and the listing description. Soooooo beautiful and convenient, appointed with everything you could need and such gracious hosts. Never wanted to leave!!!

Guest favourite

Cabin in Litchfield County

4.75 out of 5 average rating, 12 reviews

Blackberry Cottage

SandyRating, 5 stars1 day ago

We had such a wonderful stay! The home was spotless, cozy, and had everything we needed for a relaxing getaway. We especially loved spending time on the porch — such a peaceful spot to unwind, with the soothing sounds of the river in the background. Our dog was in absolute heaven, running around the yard and lounging on the porch right along with us! Everything about the experience was seamless, from check-in to communication with the host. We’d absolutely stay again — thank you for sharing your beautiful space with us!

Apartment in Winsted

4.79 out of 5 average rating, 43 reviews

Peaceful country getaway from the hectic city life

JeffreyRating, 5 stars8 months ago

Nice clean and comfortable space just like the pictures and description showed. The host resolved a small issue in a prompt and effective manner. Thank you!

Apartment in Collinsville

5 out of 5 average rating, 3 reviews

Collinsville Overlook at LaSalle

DottieRating, 5 stars1 week ago

Our stay here was wonderful. The apartment was spotless, tastefully decorated and well equipped. Check in was very easy and William was quick to respond and very accommodating. I would definitely stay here again and would highly recommend to anyone who loves to check out the many nearby walking trails or is into kayaking as the rentals are basically across the street. Also, the LaSalle Grille is a bonus being right downstairs and very good and convenient.

Home in Winsted

5 out of 5 average rating, 4 reviews

Enjoy Summer in the Berkshires

TabithaRating, 5 stars10 months ago

What . an . absolute . delight! This place was fantasic and the hosts were amazing! *WELL-STOCKED* kitchen! Didn’t need to bring a thing! We had a small group of us who were up for a board game weekend and this was the perfect setup! Plenty of tables, with comfortable rooms and seating! Beautiful scenery (definitely worth a walk/look around the area and the property - the hosts even provide maps for hiking purposes)! The hosts were phenomenal! They were incredibly proactive, responsive, and simply lovely to work with! Our group even had a few hiccups during travel and the hosts were so accommodating with checking in and out! The expectations for the property were crystal clear and they provided so much information for local activities as well! They even had a little welcome gift and card, which was so sweet and personal! ☺️ If the scenery doesn’t captivate you then the artwork certainly will! Just a fun, if not, delightful place to be! We’re already planning our next stay here!

Top Guest favourite