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Simsbury Vacation Rentals

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    $223 Average
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    Don't let other travelers get your favorite Simsbury area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Simsbury
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    The following rentals are within 25 miles of Simsbury.
    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    Granville, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bright, cheery contemporary ranch style home1 / 20
    (1)Excellent
    Cromwell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Hot Tub
    • Washer
    • Secure Parking
    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 15, 2015
    I loved staying at this comfortable home. The area, Middletown CT is centrally located and the home,on Rolling Green is centrally located. It's about 20 minutes from everywhere...
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    About this property
    This house is bright and cheerful even during winter months due to the large paladian windows and cathedral ceilings.<BR>If you find that you are traveling to Connecticut for work assignment or vacation, consider this option to hotel living.<BR>Our home will welcome you from travel or work with...
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    Location Information
    Cromwell, Connecticut 06457
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Manchester
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1904 by renowned architect Charles Platt and home to Clifford Cheney, the mansion is now registered as a national historic landmark. Located only 15 minutes from Hartford but feels like a world away. Enjoy the expansive views of the Great Lawn from every South facing window in the home....
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    Location Information
    Manchester, Connecticut 06040
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,...
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    Location Information
    Barkhamsted, Connecticut 06063
    Rental Home - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    Winsted
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake house totally rebuilt in 2016 to high standards. Very warm in cold months, central air in summer. Waterski in Summer, snow ski in winter at nearby local ski mountains (Sundown and Mohawk). Choice location on beautiful lake with full boating. Dockage for your boat directly in front of...
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    Location Information
    Winsted, Connecticut 06098
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hartford
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Sauna
    • Hot Tub
    • Central Heating
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house sits on 2.6 wooded acres, and there are a total of 9 rooms which includes: UPPER LEVEL: Four bedrooms, two baths, large dining room and kitchen overlooking mountain and deck, 32 inch TV, WiFi, and full kitchen awaiting the chef. There is a King bed in Master bedroom, a Queen in Guest...
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    Location Information
    Hartford, Connecticut 06019
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Granby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Patio
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large home has three bedrooms on one floor and there is a finished basement with new laundry machines and plenty of storage, as well as new fridge with icemaker and ceramic cooktop. Everything is clean and odor-free and there is a large bright open kitchen with sliders to a back deck and...
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    Location Information
    Granby, Connecticut 06035
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Agawam, MA
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit Agawam in comfort when you stay at this cozy vacation rental studio that sleeps 5, only a few minutes drive south from Springfield! Complete with a well-equipped kitchen, a plush queen-sized bed and a cozy lounge area with a flat-screen cable TV, this studio is perfect for families and...
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    Location Information
    Agawam, Massachusetts 01001
    Condo/Apartment - 1 Bathroom, Sleeps 5
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    West Springfield, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lily's Lodge is your Home away from Home in Western Massachusetts. We are located directly across the street from the Eastern States Exposition Fairgrounds, minutes from downtown Springfield and within 5-15 minute drive to area colleges, Basketball Hall of Fame, and Six Flags. We provide our...
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    Location Information
    West Springfield, Massachusetts 01089
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Secure Parking
    • Patio
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Windy Top Cottage is an old stone building constructed in 1935 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to “summer” in the early part of the 20th Century. The cottage was the place where the domestic staff stayed when...
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    Location Information
    North Granby, Connecticut 06060
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, furnished, deluxe condo in the core of Portland, Oregon…with fantastic views of the West Hills, PSU, and Downtown Portland. The condo is just East of the Portland State University Campus. Rented on a month by month basis. Convenient to all aspects. Attributes: √ Near the top of the...
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    Location Information
    Portland, Connecticut 97201 2249
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Quiet first floor apartment in Torrington1 / 12
    (5)Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Parking
    • Porch
    • Balcony
    • Terrace
    • Wi-Fi
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 6, 2017
    The apartment is perfect. The entire place is renovated inside and it is just what Ineeded. There is no other place in Torrington that is this nice and accommodating. Denis...
    Reviewed August 3, 2017
    Denis is a great host, and the apartment is wonderful. To say that it is well appointed is an understatement. It is roomy and light, and the balcony is a plus. It seems that...
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    About this property
    Large apartment, windows on 3 sides, new appliances, Wi-Fi, Conveniently situated on Main street downtown Torrington, from one to ten minutes away from restaurants, ten minutes away from movies theater, ten minutes away from the Post office, and all this is walking time to these locations, one...
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    Location Information
    Torrington, Connecticut 06790
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Meriden
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Satellite TV
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, Spacious, bright and outward room studio with fireplace for a relaxing or romantic getaway. The fireplace area is a favorite spot for people, who enjoy quiet, relaxing and private time. The studio also comes with a modern, fully equipped bathroom, Laundry and plenty of closet space. LBGTQ...
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    Location Information
    Meriden, Connecticut 06450
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Corner Cottage in 16 Acres Springfield1 / 8
    (1)Excellent
    East Longmeadow, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Satellite TV
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 14, 2017
    peaceful and good host we would stay again and recommend her place to anyone also close to any stores
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    About this property
    Corner Cottage. This is a private house. It is a house-share. There are 2 adults and 2 cats living in the home. My home is very bright and sunny. My place is close to family-friendly activities, nightlife, and public transport. You’ll love my place because it is quiet and because of the location....
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    Location Information
    East Longmeadow, Massachusetts 01128
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Simsbury Flight and Weather Info
    Airports nearby (1)
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    BDL
    Bradley Intl Airport
    7.3 miles from Simsbury
    Low airfares recently found by TripAdvisor travelers
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    Local Weather
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    57° 36°
    October
    45° 28°
    November
    35° 20°
    December

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