Holiday rentals in Simsbury

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Top-rated holiday rentals in Simsbury

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Guest favourite

Guest suite in Wethersfield

4.99 out of 5 average rating, 278 reviews

Bright, clean studio in charming Old Wethersfield

Clean, bright studio apartment in the charming village of Old Wethersfield. Stroll to cafes, village green, historic homes and museums. Minutes from I-91 with easy commuting access to downtown Hartford, business and tourist sites, universities, and Hartford Hospital/CCMC. The studio is an in-law suite above our garage. It is attached to our home but has its own keyed entrance. It has a full kitchen, bathroom with shower over tub, closet, queen-sized bed, kitchen table/chairs, and workspace.

Guest favourite

Home in Bloomfield

4.95 out of 5 average rating, 103 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods near Wintonbury Hills Golf course. Neighborhood setting and on a private corner lot. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails too! Close to Ski Sundown, Mt Tom, MGM Casino, tons of golf courses, beaches.

Guest favourite

Guest suite in Vernon

4.98 out of 5 average rating, 166 reviews

Laura's Loft and Gallery, private suite

Unique and roomy space with private entrance, two bedrooms, full bath with tub shower, and plenty of room to relax. Kitchen space has mini fridge, microwave, toaster oven, hot plate, and crock pot. Pleasant living area opening to 2nd floor deck. WiFi with Ethernet also, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup for your breakfast included, and homemade scones in seasonal flavors.

Superhost

Rental unit in Windsor Locks

4.85 out of 5 average rating, 126 reviews

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Guest favourite

Rental unit in West Granby

4.9 out of 5 average rating, 129 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the Joab Griffin House. We are a beautiful historic farmhouse set on a private hill tucked away in the foothills of the Berkshires, surrounded by gorgeous farmland and hundreds of acres of land trust and game refuge trails, streams, and waterfalls within a five-minute walk from your door. Enjoy a private apartment in this lovely farmhouse. Here, you'll find cool summer breezes, cozy, warm, sun-filled days, and star-filled skies with the sounds of the brook outside your window.

Guest favourite

Loft in Tolland

4.98 out of 5 average rating, 171 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Guest favourite

Rental unit in Litchfield

4.98 out of 5 average rating, 116 reviews

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Guest favourite

Guest suite in East Granby

4.85 out of 5 average rating, 316 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

Guest favourite

Guest house in Granby

4.89 out of 5 average rating, 213 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!

Guest favourite

Cottage in Granby

4.87 out of 5 average rating, 157 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.

Guest favourite

Farm stay in Granby

4.89 out of 5 average rating, 267 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.

Guest favourite

Cottage in Collinsville

4.97 out of 5 average rating, 120 reviews

The Carriage House

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, fish and swim. Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.