
Holiday houses in Harwinton
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Top-rated holiday rentals in Harwinton
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Home in Litchfield County on a MAIN ROAD!
Conveniently located on a MAIN ROAD in the heart of Torrington, this cozy homestead makes for the perfect New England getaway - seasonal activities to endure such as: hiking, swimming, kayaking, apple/pumpkin picking, skiing/snowboarding, and breweries & wineries. Close to Torrington’s historic downtown district featuring the Warner Theater & Kidsplay Museum. Conveniently located between a convenience store and some of Torrington’s finest coffee right next door from the Batchy Brew coffee truck.
FamilyValueBackyard
4.86 out of 5 average rating, 133 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
FamilyLocationBreakfast
4.99 out of 5 average rating, 159 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.
FamilyLocationAmenities
4.99 out of 5 average rating, 120 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.
LocationFamilyWalkability
4.95 out of 5 average rating, 292 reviews
Charming 3BR Hill House *Remodeled* w/Arcade
The Lindan Hill House is a perfect AirBnb balance of luxury and value! Stay and play as you enjoy our 5 Star remodeled charming home in Terryville. This quaint and comfy home has everything you need to enjoy your stay including 3 BR with a King/Queen/2 Twin beds with premium bedding. The cozy remodeled basement is perfect for popcorn and movies, dinner and drinks at the bar, and has a game/arcade room with foosball, checkers/chess, and tons of board games! See below for a video tour.
FamilyLocationNearby
4.95 out of 5 average rating, 137 reviews
1800’s Farmhouse in the hills of Litchfield County
Welcome to our 1800s farmhouse on 2 acres in the hills of Litchfield County, surrounded by hiking trails, lakes, skiing, wineries, and the antique trail! This 4-bedroom home features a living room with wood-burning fireplace. Upstairs library/reading area with curated books. The dining room seats eight with pellet stove. Enjoy the outdoor dining area, grill, and fire pit. Very close to ski resorts, wineries, and lakes for kayaking/swimming, and many picturesque colonial towns!
LocationFamilyQuiet
5.0 out of 5 average rating, 33 reviews
Stylish & Luxurious 3 BDR home with Play Station
Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with a 2-car garage, ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!
ValueLocationLong stay
4.84 out of 5 average rating, 121 reviews
Storybook Cape...HOST & Co.
Step back in time in this classic 1930s Cape Cod home, nestled in the serene beauty of the Litchfield Hills. Just a five-minute drive from the charming Litchfield Green, you’ll find antique shops, cozy cafés, unique boutiques, and a picturesque town center perfect for unwinding. Outdoor lovers will appreciate the proximity to the trails and wildlife of White Memorial Foundation, the peaceful beauty of Topsmead State Forest, and winter adventures at Mohawk Mt. Ski Area.
ValueLocationAccuracy
4.98 out of 5 average rating, 258 reviews
Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes
This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area
ValueFamilySkiing
4.87 out of 5 average rating, 413 reviews
Cozy Family Home - Kid & Pet Friendly
3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.
FamilyValueParks
4.92 out of 5 average rating, 242 reviews
Litchfield County Farmhouse with a Modern Twist
Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.
ValueFamilyTV
4.98 out of 5 average rating, 336 reviews
Garden View Apartment on Main St. Walk to Downtown
A simple, comfortable stay in downtown Torrington, nestled in the Litchfield Hills. This private garden-view apartment in a quiet 3-family home offers fast WiFi and free off-street parking. Walk to restaurants, shops, grab ice cream, and catch a show at the Warner Theatre, or stay in and enjoy the garden with a koi pond. Close to hiking trails and scenic views. A relaxing midpoint ~2 hours from NYC and Boston.
FamilyLocationBathroom
4.99 out of 5 average rating, 245 reviewsPopular amenities for Harwinton holiday rentals
Other great holiday rentals in Harwinton

Clean & Quiet Home| Enclosed 3 Season Porch & Deck
FamilyValueGetting around
5.0 out of 5 average rating, 69 reviews
Spacious Country Comfort
LocationFamilyNearby
5.0 out of 5 average rating, 71 reviews
The Main Farmhouse at Gray Rock Farm
FamilyValueComfort
5.0 out of 5 average rating, 61 reviews
Cozy Farmhouse Style 3 Beds | Near Downtown
FamilyLocationKitchen
4.85 out of 5 average rating, 73 reviews
The Doctor’s 1781 House on the Litchfield Green
LocationFamilyWalkability
4.98 out of 5 average rating, 55 reviews
SerenityCT
FamilyLocationAmenities
5.0 out of 5 average rating, 52 reviews
Cozy barn apt in Litchfield
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 14 reviews
Highland Lakefront Retreat
FamilyLocationKitchen
4.9 out of 5 average rating, 49 reviewsDestinations to explore
- Yale University
- Six Flags New England
- Fairfield Beach
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Taconic State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Hammonasset Beach State Park
- Bousquet Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Sherwood Island State Park
- Ski Sundown
- Benmarl Winery
- Wesleyan University
- Naumkeag
- Poets' Walk Park





