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Simsbury Vacation Rentals

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    $212 Average
    $0$1,000+
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    All 14 Rentals in Simsbury
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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.
    Simsbury
    4 Bedrooms, Sleeps 8Quick View
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    The following rentals are within 25 miles of Simsbury.
    East Longmeadow, MA
    1 Review
    1 Bedroom, Sleeps 2Quick View
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    Torrington
    3 Reviews
    1 Bedroom, Sleeps 2Quick View
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    Bloomfield
    4 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BEAUTIFUL 100% NEWLY renovated Victorian Mansion, on 3.5 acre private ESTATE., directly alongside the ELEGANT greens and fairways of the prestigious private TUMBLE BROOK COUNTRY CLUB. LARGE INGROUND SWIMMING POOL. Great GOLF COURSE views from every window. PRIVATE- AWAY FROM THE ROADS- Large,...
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    Location Information
    Bloomfield, Connecticut 06002
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    West Springfield, MA
    2 Bedrooms, Sleeps 9Quick 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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    Granville, MA
    3 Bedrooms, Sleeps 6Quick View
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    Amenities & Details
    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the...
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    Location Information
    Granville, Berkshires 01034
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cromwell
    1 Review
    3 Bedrooms, Sleeps 6Quick 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
    Excellent of 5 bubbles
    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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    Barkhamsted
    6 Bedrooms, Sleeps 12Quick 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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    Litchfield
    3 Bedrooms, Sleeps 7Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Parking
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bathroom vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property that sits on a half acre of land and offers a spacious backyard with a deck and patio. Stylish, high-end decor adorns the interior, making...
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    Location Information
    Litchfield, Connecticut 06750
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Agawam, MA
    Studio, Sleeps 5Quick View
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    Amenities & Details
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Patio
    • Satellite TV
    • Internet Access
    • Shared Yard
    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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    Winsted
    3 Bedrooms, Sleeps 6Quick 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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    Portland
    1 Bedroom, Sleeps 2Quick 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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    Litchfield
    3 Bedrooms, Sleeps 5Quick View
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    Amenities & Details
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set on the edge of a valley with westerly views on a beautiful street in Litchfield this vintage home has all modern amenities and style. Has a well in the mudroom and the steep staircase to give you a really authentic 1820's retreat. A large park-like yard with old granite barn foundations and...
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    Location Information
    Litchfield, Connecticut 06759
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Meriden
    Studio, Sleeps 2Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Yard
    • Secure Parking
    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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    Simsbury Flight and Weather Info
    Airports nearby (1)
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    BDL
    Bradley Intl Airport
    7.3 miles from Simsbury
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