Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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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

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.

ValueLocationAccess

4.99 out of 5 average rating, 250 reviews

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

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! 🦉

LocationFamilyComfort

4.95 out of 5 average rating, 129 reviews

Guest favorite

A modern tiny home is nestled among tall trees, featuring a sleek black exterior. A fenced patio area is visible in front, with greenery in the surrounding landscape. Natural light highlights the entrance, enhancing the inviting ambiance of the retreat.

Tiny home in New Hartford

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!

ValueLocationBackyard

4.9 out of 5 average rating, 99 reviews

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

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.

ValueFamilyKitchen

4.97 out of 5 average rating, 78 reviews

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

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!

LocationFamilyTV

4.95 out of 5 average rating, 39 reviews

Guest favorite

Home in Winchester

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.

FamilyValuePool

4.89 out of 5 average rating, 46 reviews

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

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.

ValueFamilyBackyard

4.97 out of 5 average rating, 232 reviews

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

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.

ValueLocationParking

5.0 out of 5 average rating, 123 reviews

Top guest favorite

An exterior view of the teahouse displays its rustic wooden structure nestled among lush greenery. A spacious wrap-around porch with wooden railings is visible, along with multiple windows allowing natural light. The surrounding foliage offers a natural ambiance.

Cottage in Falls Village

Retreat w 50 acre forest, waterfalls, tennis/bball

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (hike, sledding, 5 minutes from Mohawk Mtn Skiing). Hand built, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. Video: "Cornwall Hollow Teahouse" on YT or IG

LocationFamilyOutdoor spaces

4.99 out of 5 average rating, 133 reviews

Top guest favorite

A serene bedroom is presented with a spacious bed adorned with soft linens and a cozy throw. Two bedside tables hold elegant lamps, and natural light floods the room through large windows. A decorative wreath hangs above the headboard, enhancing the tranquil ambiance.

Home in Sheffield

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

FamilyLocationDecor

4.99 out of 5 average rating, 133 reviews

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

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!

FamilyLocationCheckout

4.91 out of 5 average rating, 67 reviews

Top guest favorite

A cozy living area features a brown leather sofa with white throw pillows, positioned beside a window that allows natural light. A wooden coffee table sits atop a blue and white woven rug, complemented by a comfortable armchair. Shelves display decorative items and fresh flowers add a welcoming touch.

Cabin in Litchfield County

Blackberry Cottage

Enjoy our peaceful (pet friendly) home, just a short drive to the center of Norfolk. Great for friends and/or family visits. Board games, puzzles and books inside for all; fire pit outside. Front & side decks, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. I think you’ll love it!

ValueFamilyAir conditioning

4.94 out of 5 average rating, 158 reviews