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.

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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, 235 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.

Top guest favorite
The exterior of a newly renovated schoolhouse is depicted, showcasing a welcoming entrance with a red door. Surrounding greenery includes well-maintained lawns and established trees. A carriage house is visible on the left, complementing the charming architecture of the main house.
Home in Collinsville
4.96 out of 5 average rating, 116 reviews

Nature Lovers Retreat-Wine Vineyards Skiing nearby

Sleeps 6! 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 , canoeing kayak rentals

Guest favorite
A spacious living area is presented, featuring a comfortable gray sectional sofa, a wooden coffee table, and a decorative rug. Two green bar stools are positioned at a small counter, and a ceiling fan is mounted above, enhancing the cozy atmosphere of the penthouse apartment.
Home in West Hartford
4.89 out of 5 average rating, 123 reviews

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.

Top guest favorite
A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.
Home in Southington
4.94 out of 5 average rating, 127 reviews

Connecticut Chalet: Winter Nights by the Fire

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.

Guest favorite
The living room features refinished hardwood floors and a neutral colour palette. A spacious sofa and an armchair are arranged around a coffee table, facing a large flat-screen TV mounted above a decorative fireplace. Light streams in through large windows, enhancing the airy feel.
Home in Terryville
4.96 out of 5 average rating, 128 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.

Superhost
A bright living area features a teal sofa paired with a light gray armchair, accented by a round coffee table at the center. Natural light floods in through large windows, with soft curtains enhancing the serene atmosphere. Art pieces adorn the walls, complementing the hardwood floor.
Home in Bristol
4.84 out of 5 average rating, 107 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!

Top guest favorite
The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.
Home in Bristol
4.93 out of 5 average rating, 212 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.

Guest favorite
A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.
Home in Feeding Hills
4.89 out of 5 average rating, 1,021 reviews

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.

Top guest favorite
A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.
Home in Collinsville
4.99 out of 5 average rating, 128 reviews

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!

Top guest favorite
A view of a classic farmhouse, surrounded by green grass and trees. Hay is scattered across the foreground, and the house features a porch with visible outdoor seating. A quiet road is seen in the distance, offering a glimpse of the serene rural setting.
Home in Bethlehem
4.97 out of 5 average rating, 316 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.

Top guest favorite
The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.
Home in Otis
4.95 out of 5 average rating, 170 reviews

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

Guest favorite
A bright living room features a cozy arrangement with a gray sofa and two wooden chairs. A simple coffee table displays decorative items and a potted plant. Natural light streams through two windows, adorned with bamboo shades, creating a warm and inviting space.
Home in New Hartford
4.89 out of 5 average rating, 150 reviews

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

When is the best time to visit Simsbury?

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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.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 1,220 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • 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

  • 4.7 Average rating

    Simsbury stays receive an average rating of 4.7 out of 5 from guests