Holiday houses in Winchester

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.

Value · Location · Decor

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 & no crazy rules! Surrounded by acres nature! Private-Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!🦉

Location · Family · Check-in

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.

Family · Location · Breakfast

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.

Value · Location · Getting around

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Family · Value · Getting around

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!

Family · Location · Hospitality

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.

Location · Value · Air conditioning

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.

Location · Value · Parks

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.

Family · Value · Condition

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

Family · Location · Barbecue

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!

Family · Location · Bathroom

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!

Location · Family · Accuracy