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Simsbury Vacation Rentals

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    All 25 Rentals in Simsbury
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    The following rentals are within 20 miles of Simsbury.
    Lily's Lodge1 / 6
    (1)Excellent
    West Springfield, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Windy Top Stone Cottage1 / 26
    (1)Excellent
    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Three-bedroom one-and-a-half bath ranch with lots of room inside and outside1 / 17
    (1)Excellent
    Granby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Quiet first floor apartment in Torrington1 / 12
    (6)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 December 30, 2017
    Apartment was neat, clean and beautifully furnished. The hosts, who are warm and inviting, thought of everything. View from the apartment is stunning even in winter. Convenience...
    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...
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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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    Torrington, Connecticut 06790
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/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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    Bloomfield, Connecticut 06002
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Springfield, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Private Yard
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New Polished single-family home with 4 bedrooms.! You have the Entire house to yourself. Visit Springfield, Massachusetts where you can stay at this nice, classic authentic, beautiful vacation rental located in the forest park neighborhood, near Massmutual, downtown Springfield,...
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    Springfield, Massachusetts 01108
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Loft at Lost Acres is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of the Lost Acres Vineyard service barn. Originally intended for the caretaker, the owners have decided to offer it to the public to enjoy the beauty of the vines & the...
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    North Granby, Connecticut 06060
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bright, cheery contemporary ranch style home1 / 17
    (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. If you find that you are traveling to Connecticut for work assignment or vacation, consider this option to hotel living. Our home will welcome you from travel or work with it's...
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    Cromwell, Connecticut 06457
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vernon
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 3 story lake front home has a great yard and private beach with dock and floating swim platform. There is a bedroom and a full bath on each floor. The lake views from the King bed in the Master suite are amazing. There is a washer & Dryer on the main floor and all your basic needs...
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    Vernon, Connecticut 06066
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Springfield, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable three bedroom home is located in an excellent neighborhood. Recently renovated, the house has a real homely feel to it. I maintain it well. All in all a great living area, with a fully equipped kitchen, 3 bedrooms with one King, one Queen, one full bed and two bathrooms. It’s the...
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    Location Information
    Springfield, Massachusetts 01109
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Cable/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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    Winsted
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Private Yard
    • Parking
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake house rebuilt in 2016 to high standards. Lake front, swimming, fishing, kayaking. Central air. Choice location on beautiful lake with full boating. Dockage for your boat directly in front of the cottage. Nice, direct waterfront with lawn, deck and good swimming area. Gas fireplace and very...
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    Winsted, Connecticut 06098
    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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    Manchester, Connecticut 06040
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Hartford
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Grill
    • Central Heating
    • Sauna
    • Mountain Views
    • Washer
    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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    Hartford, Connecticut 06019
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Zen Urban Flat near Downtown Springfield1 / 13
    (1)Excellent
    Springfield, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 12, 2018
    This place was beautiful. Nice and clean. Very convenient. And our host was very helpful. She told us the best places to visit in the area. I’ve been all around the world. And...
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    About this property
    This beautiful 3 bedroom apartment is located in Old Hill neighborhood, conveniently close to downtown, museums, and colleges. Easy access to highways and public transportation and It is 20 minutes away from Bradley International airport. We welcome everyone. Come and enjoy a home away from home....
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    Location Information
    Springfield, Massachusetts 01109
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Colebrook
    3 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Private Yard
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our tastefully decorated home in Colebrook - nestled in the woodlands, this two-acre retreat offers a tranquil escape for up to 6 people and is only a 5-minute drive from town. Curl up by the fire in the family room or grab a blanket and make some smores around the fire pit! Perfect for...
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    Colebrook, Connecticut 06021
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 16
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    Harwinton
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Weekly rental April through December, monthly rental offered January thu March. 2 bedroom, 1 bath, fireplace, with beautiful views of the lake Enjoy a classic New England vacation in this direct lake front home on Harwinton Lake. Relax and enjoy the pretty scenery and breezes in this quiet lake...
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    Harwinton, Connecticut 06791
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cromwell
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Children's Pool
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious townhome is in the desirable Fox Meadows Condo complex in Cromwell, cT; home to the Tournament Players Golf Club. The condo offers vaulted ceilings and lots of natural light. The lower level has a garage with remote control and a workout room. The main level houses a living room,...
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    Cromwell, Connecticut 06416
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Granville, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr Black Rabbit Farm has the Berkshire mountain range rising before you, this campsite is located on a very unique farm. Black Rabbit Farm offers a wide range of artisan provisions in the farm store as well as their celebrated wild ales, you will be delighting in the best of life. This is...
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    Granville, Berkshires 01077
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bristol
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy fully furnished four room apartment with fully functioning kitchen. Completely remodeled in 2016 from floor to ceiling. Off street parking in private driveway. The apartment is pet and smoke free. This Apartment is perfect for the traveling professional. The apartment is attached to an...
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    Location Information
    Bristol, Connecticut 06010
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hartford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Apt is nice and comfortable,very close to downtown Hartford,two hrs away from New York,I am renting out my extra room,you will enjoy staying here as I am a nice and friendly person,please make sure you respect yourself by acting appropriate,this is why I would mostly prefer a woman living with...
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    Hartford, Connecticut 06105
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    West Hartland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your lakeside retreat at this 3-bedroom, 2-bathroom vacation rental home that has accommodations for 8 in Tolland. Dive into lakeside fun on your private dock and hop on a kayak or stand-up paddleboard for a day of exploring this peaceful lake. When you’re not at the lake, enjoy fabulous...
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    West Hartland, Connecticut 01034
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Agawam, MA
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    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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    Agawam, Massachusetts 01001
    Condo/Apartment - 1 Bathroom, Sleeps 5
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    Springfield, MA
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Washer
    • Terrace
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note that this property features exterior security cameras on the front porch. These do not look into any interior spaces * Book your Springfield getaway to 'Lil Lubb's Layout,' a recently updated 2-bedroom, 2.5-bath vacation rental just 2 miles from downtown. With enough space to...
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    Location Information
    Springfield, Massachusetts 01109
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    West Hartford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak in all that Hartford has to offer from this 2,000-square-foot home tucked in a quiet corner of West Hartford! From the 3-bedroom, 2.5-bathroom house, easily visit the rose gardens at Elizabeth Park, the Mark Twain House & Museum, and the Wadsworth-Atheneum Museum of Art. After days spent...
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    Location Information
    West Hartford, Connecticut 06117
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Simsbury Flight and Weather Info
    Airports nearby (1)
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    Bradley Intl Airport
    7.1 miles from Simsbury
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