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Windsor Vacation Rentals

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    All 25 Rentals in Windsor
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    The following rentals are within 20 miles of Windsor.
    East Hampton lakefront lakehouse1 / 21
    (3)Very good
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3/2 Private Lakefront Home 4 steps to the water-Kayaks, Canoe & Fire Pit1 / 35
    (2)Excellent
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lily's Lodge1 / 6
    (1)Excellent
    West Springfield, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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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
    Manchester
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Central Heating
    • Patio
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    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
    Springfield, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Springfield, Massachusetts 01109
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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
    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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    • Secure Parking
    • Patio
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 30, 2018
    This home was perfect for us! One-level living was key because my daughter was on crutches. Dianne takes great pride in keeping her home immaculate. Thank you Dianne!
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    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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    Granby, Connecticut 06035
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Springfield, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Yard
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    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
    Bright, cheery contemporary ranch style home1 / 17
    (1)Excellent
    Cromwell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Zen Urban Flat near Downtown Springfield1 / 13
    (1)Excellent
    Springfield, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    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
    Corner Cottage in 16 Acres Springfield1 / 8
    (1)Excellent
    East Longmeadow, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Yard
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    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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    East Longmeadow, Massachusetts 01128
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Hartford
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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
    Marlborough
    9 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadowbrook Estate- Elegance in the peaceful countryside. ELEGANT ACCOMODATIONS for the wedding party, the bridal party, the groom’s family, renewal of vows, golden anniversaries , family reunions, or Wellness/Corporate Retreats. The Estate’s 8,000-sq ft space,...
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    Marlborough, Connecticut 06447
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 22
    Granville, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    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
    East Hartford
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in bliss as you imagine yourself enjoying breakfast in this picturesque eat-in kitchen. Conveniently located just 10 minutes to Downtown Hartford, Manchester, and South Windsor you'll find yourself with endless options for restaurants, shopping, parks, and entertainment. Enjoy...
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    East Hartford, Connecticut 06108
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    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
    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
    Stafford Springs
    1 Bedroom, 4 Bathrooms, Sleeps 2 Quick View
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    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the Green Room with private bath and queen bed, perfect for the couple who wants to Practice a screenplay and maybe even experience some paranormal activity. not for the faint of heart! Shooting balls of light, orbs, apparitions and whistlers may be experienced. Practice your dance routine,...
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    Stafford Springs, Connecticut 06076
    Condo/Apartment - 1 Bedroom, 4 Bathrooms, Sleeps 2
    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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    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
    Bristol
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Central Heating
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    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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    Bristol, Connecticut 06010
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    Portland, Connecticut 97201 2249
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Springfield, MA
    2 Bedrooms, 3 Bathrooms, Sleeps 4 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
    Book your Springfield getaway to 'Lil Lubb's Layout,' a recently updated 2-bedroom, 2.5-bath vacation rental just 2 miles from downtown. This historic 2,000-square-foot abode offers a tastefully furnished interior, private deck, and a newly landscaped yard with a quaint patio. Explore downtown or...
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    Springfield, Massachusetts 01109
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    West Hartford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    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
    Windsor Flight and Weather Info
    Airports nearby (1)
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    Bradley Intl Airport
    6.3 miles from Windsor
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