Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

4.99 out of 5 average rating, 249 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

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Top guest favorite

Apartment in Torrington

4.99 out of 5 average rating, 158 reviews

“The Clemons!” Central AC - 3 Beds - Main Level

Originally Built by the Hotchkiss Lumber company (one of Torrington’s first industrial manufacturing factories) for their daughter - the Clemons’ Family, this home offers lots of room to stretch out in this 3 bedroom, living/kitchen/ & 1.5 baths in this first floor unit. All beds feature soft organic blend sheets, soft/firm pillows with protectors , Brand new Central Air Conditioning in summer and hot air heating, fans and an air purifier. 2 Roku TVs. Close to ski areas, IDEAL for wedding guest

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Guest favorite

A serene pond reflects the surrounding greenery, with kayaks resting on the shore. A cozy cabin is visible in the background, framed by trees. The tranquil setting invites outdoor activities such as swimming or fishing, creating a peaceful natural atmosphere.

Cabin in Colebrook

4.95 out of 5 average rating, 129 reviews

Rustic Pond Cabin: Nature, Stars & Serenity

🦉Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. All natural pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay n walk the trail around the pond, have campfires outside in firepit! Clean and no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires! 🦉

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Guest favorite

The cottage, elevated on a stone base, features a large front deck and large windows inviting plenty of natural light. Surrounded by trees, a grassy area leads to the lakefront, showcasing a serene atmosphere. A dock extends into the water, providing access to the lake.

Cottage in Winchester

4.97 out of 5 average rating, 78 reviews

Winsted/Highland Lake/Direct Waterfront/Immaculate

"Lone Pine Cottage" - High-quality direct lakefront on Highland Lake in Winsted. It is a 2016 total rebuild in charming Lake-Cottage style, nostalgic while utterly modern. Beautiful 2 bed 2 bath, large deck and dock slip in front cottage. Best of locations on Highland Lake. !) East side of the lake with preferred sun exposure. 2) Great, usable swimming area, (shallow for smaller kids, gradually deepening for adults). 3) Not impacted by heavier boat traffic. Central air. WIFI.

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Top guest favorite

The image captures a serene view of a lake at dusk, reflecting soft hues of pink and blue in the sky. Gentle ripples are seen across the water's surface, creating a tranquil atmosphere, with trees and houses lining the distant shore.

Home in Winsted

4.95 out of 5 average rating, 39 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!

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Top guest favorite

Home in Winchester

4.93 out of 5 average rating, 45 reviews

Highland Lakefront Retreat

Welcome to your private escape on Highland Lake — a beautifully renovated lakefront home offering stunning views, direct water access, and year-round serenity. Enjoy morning coffee on the deck overlooking the water, spend afternoons kayaking or swimming from your private dock, and wind down with sunset views by the fire pit. Whether you're planning a family vacation, couples’ retreat, or remote work escape, this lake house offers the perfect blend of comfort, charm, and natural beauty.

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Top guest favorite

A cozy living area features a light-colored sofa alongside a woven chair and a circular patterned ottoman. Large windows provide natural light, while a decorative fish hangs from the ceiling. A small plant and a lamp add subtle touches to the inviting space.

Cottage in Winsted

4.93 out of 5 average rating, 58 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.

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Top guest favorite

A two-story chalet-style house is framed by lush greenery and colorful landscaping. A gravel driveway leads up to the home, which features a welcoming porch with a decorative American flag. The first floor is supported by a lower level that includes outdoor amenities.

Guest suite in Winchester

4.97 out of 5 average rating, 232 reviews

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom 1 bath private suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private deck. Moon or star gazing by night. We follow all Airbnb policies & State of CT 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.

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Top guest favorite

The living area features a comfortable sofa and two armchairs, accented with a patterned rug. A dining area with wooden stools is positioned adjacent to a kitchen equipped with modern appliances. Natural light enters through large windows, enhancing the warm and inviting space.

Apartment in Torrington

5.0 out of 5 average rating, 123 reviews

Pristine Downtown 2BR Cozy Fireplace & Parking

Stay in a professionally cleaned, cozy, 1st floor, 2BR apartment designed for comfortable short stays, weekend visits, work trips, and longer stays alike. Located just minutes from downtown Torrington, you’ll be within minutes of restaurants, coffee shops, the Warner Theatre, Nutmeg Ballet, and local events while still enjoying a relaxing place to unwind after a busy day. Our goal is simple: A spotless, comfortable, and stress-free stay that feels easy from check-in to checkout.

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Guest favorite

An aerial view captures the Inn at Highland Lake, nestled by the waterfront. A grassy yard bordered by trees features a picnic table, while a dock extends into the lake, providing access to water activities. The surrounding area shows additional greenery and boats.

Apartment in Winsted

4.91 out of 5 average rating, 67 reviews

2nd Floor The Inn at Highland Lake

Welcome to the Inn at Highland Lake. This second floor unit of the lakehouse offers a fully furnished 3-Bedroom 1-Bathroom with a spacious sunroom overlooking Highland Lake. This space includes a full kitchen, two common areas, one with a pull-out sofa bed and a shared washer/dryer. There is a waterfront yard across the street with a dock. During your stay, get a 25% discount off all the boat and watercraft rentals at the Marina at Highland Lake right next door!

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Guest favorite

Barn in Canaan

5.0 out of 5 average rating, 5 reviews

The Cobble Barn | Fireplace • A/C • Screened Porch

Welcome to The Cobble Barn, a thoughtfully converted timber barn at the base of Cobble Mountain in Connecticut's Northwest Corner. Soaring beams, a wood-burning fireplace, screened porch and modern comforts create an inviting place to slow down. Walk to coffee, breakfast and essentials, then return to mountain views, quiet evenings and the character of a home unlike any other.

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Apartment in Winsted

4.87 out of 5 average rating, 183 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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