
House vacation rentals in Simsbury
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Top-rated house rentals in Simsbury
Guests agree: these houses 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.

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.

WeHa Penthouse w/ Private Deck
Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Connecticut Chalet: Experience Fall in New England
Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Nature Lovers Retreat-Wine Vineyards Skiing nearby
Newly renovated 1910 schoolhouse. You'll love 2-3 bdr, clean, bright well appointed home. Volume ceilings, and a well stocked kitchen for long stays. Walk to nearby historic downtown Collinsville, where you'll find antique stores, restaurants and beautiful New England scenery. The CT wine trail and Brignole Vinyards nearby, where you will find food trucks and live music. Walk or cycle the Farmington River Trail. You will also find hiking, fishing, skiing, SUP rentals, canoeing/ kayaking.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

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.

Farm Fresh Feeding Hills
Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Modern Farmhouse
This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.
Popular amenities for Simsbury house rentals
House rentals with a pool

Hilltop House w/POOL/SPA- HOST & Co.

Stunning luxury home with pool

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

Country retreat on 4 private acres

Lakeview Expanse

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Litchfield Hills Lakefront Getaway! Amazing Views
Weekly house rentals

Woodland Sanctuary-hot tub|fireplace|hikes|fishing

The Silhouette in Hartford

Lake Escape: Lake Cottage Charm, Lake Front, AC

Stylish & Luxurious 3 BDR home with Play Station

The Hangar

Prime West Hartford Center Location: Historic Gem

Riverside Farm

Private Woodland Sanctuary—3 mins to a lake beach!
Private house rentals

Wishing well Home away

Nest&Rest Escape

Island Vibes

Peaceful, Modern Cottage, 20 min to BDL, 2BR/1BA

Walking on Sunshine

The little house that could!

Cozy Waterfront Lake House

Guest Suite in Southington
Quick stats about house rentals in Simsbury
 - Total vacation rentals- Explore 20 vacation rentals in Simsbury 
 - Nightly prices starting at- Simsbury vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees 
 - Verified guest reviews- Over 1,170 verified reviews to help you choose 
 - Family-friendly vacation rentals- 10 properties offer extra space & kid-friendly amenities 
 - Pet-friendly vacation rentals- Find 10 rentals that welcome pets 
 - Rentals with dedicated workspaces- 10 properties have a dedicated workspace 
 - Wi-Fi availability- 20 of Simsbury vacation rentals include wi-fi access 
 - Popular amenities for guests- Guests love Kitchen, Wifi, and Pool across Simsbury rentals 
 - 4.6 Average rating- Simsbury stays receive an average rating of 4.6 out of 5 from guests 
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- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Walnut Public Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Wildemere Beach
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Clinton Beach
- Giants Neck Beach
- Bayview Beach
- Grove Beach
- Harveys Beach
- Bushnell Park
- Brimfield State Forest
- Fort Trumbull Beach
- Hammonasset Beach State Park
- Chapman Beach
- Norman Rockwell Museum
- Bigelow Hollow State Park
