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Vacation rentals in Simsbury

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Top-rated vacation rentals in Simsbury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Bethlehem

4.99 out of 5 average rating, 212 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Guesthouse in Glastonbury

4.96 out of 5 average rating, 134 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Apartment in Windsor Locks

4.85 out of 5 average rating, 110 reviews

Apt near Bradley airport Six Flags with parking

Enjoy your stay at a stylish and cozy apt. No shared or common areas other then the parking space. Renting out the whole upstairs apartment. There is no longer a dog on the property. Direct access into the apartment through the back, up the outdoor staircase. It's a short drive to the Bradley International Airport. (10 min) Bedroom has a Queen bed with fresh linens. Fully stocked kitchen: stove, oven, fridge, complimentary tea and coffee. Pots, pans, baking dishes, utensils, salt pepper.

Vacation home in Torrington

4.95 out of 5 average rating, 141 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.

Barn in Bloomfield

4.97 out of 5 average rating, 112 reviews

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Basque in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Home in Southwick

4.99 out of 5 average rating, 185 reviews

Linny's Lakeview Cottage

Linny's lakeview cottage is updated with beautiful hardwood floors. The kitchen is finished in white shaker cabinets, granite counter tops & new ss appliances. The counter joins the kitchen/living room & comfortably sits 6. This is a renovated 650 sq ft home. Access our online guidebook (a few day before your stay) for; house rules, local attractions, maps, and more, ensuring you make the most of your stay.

Guest suite in East Granby

4.84 out of 5 average rating, 288 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Guesthouse in Glastonbury

4.91 out of 5 average rating, 176 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

Guesthouse in Granby

4.89 out of 5 average rating, 196 reviews

The Loft @ Lost Acres ~ A Peaceful Rural Escape!

The Loft @ Lost Acres Vineyard is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of a Lost Acres Vineyard barn. Originally intended for the caretaker, the owners are now offering it to the public to enjoy the beauty of the vines & the stunning rural scenery of North Granby. Oh, and stop by the tasting barn, the wine is AMAZING!

Cottage in Granby

4.87 out of 5 average rating, 145 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

Apartment in Winchester

4.91 out of 5 average rating, 343 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

Farm stay in Granby

4.89 out of 5 average rating, 249 reviews

The Farmhouse at Maple View Farm

Sunny, vintage 1936 farmhouse in the center of a quintessential New England farm town. Maple View Farm is a working livestock farm with horses, ponies, pigs and chickens plus a big garden. Wake up to the sounds of the rooster and step outside to pet the horses and ponies. Our on-farm Brewery (check hours) uses local ingredients. Window A/C units in bedrooms.

Vacation rentals for every style

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Unique stays

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Popular amenities for Simsbury vacation rentals

Free parking on premises

Air conditioning

Stay near Simsbury's top sights

Talcott Mountain State Park34 locals recommend

Blue Fox Run Golf Course3 locals recommend

Stratton Brook State Park6 locals recommend

Other great vacation rentals in Simsbury

Guest suite in Morris

4.99 out of 5 average rating, 351 reviews

Lakeside Private Guest Suite

Guest suite in Windsor

4.84 out of 5 average rating, 122 reviews

Rustic Loft Apartment

Home in Granby

4.95 out of 5 average rating, 223 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

Guest suite in Wethersfield

4.99 out of 5 average rating, 262 reviews

Bright, clean studio in charming Old Wethersfield

Home in Feeding Hills

4.89 out of 5 average rating, 894 reviews

Farm Fresh Feeding Hills

Apartment in Brookfield

4.94 out of 5 average rating, 192 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Condo in Middletown

4.97 out of 5 average rating, 108 reviews

Entire place to yourself Cromwell/Middletown Line

Apartment in Portland

4.88 out of 5 average rating, 466 reviews

SUNNY PRIVATE 1 BEDROOM APARTMENT

Quick stats about vacation rentals in Simsbury

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2.1K reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Simsbury?
Four-legged friends are welcome in Simsbury. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Simsbury?
Yes! Work meets play with ease at over 20 vacation rentals in Simsbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Simsbury have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Simsbury?
Simsbury has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Simsbury?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Simsbury have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simsbury have wifi?
Absolutely! We offer over 20 house rentals with wifi in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simsbury have free parking?
Absolutely! We offer over 20 house rentals with free parking in Simsbury. Enjoy a tailored experience with all the comforts you desire.

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