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Holiday Rentals and Homes in Cheshire, CT

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    The following rentals are within 25 kilometers of Cheshire, Connecticut.

    1 / 17
    5 of 5 bubbles (14) Excellent
    Branford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 10
    Wallingford
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
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    1 / 19
    5 of 5 bubbles (9) Excellent
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 22
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Grill
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fully furnished 2 bdr apt on 1st floor in private 2-unit house. Host (owner) lives on the second floor. Only 2 blocks from downtown, Yale campus, shops, restaurants in beautiful East Rock neighborhood. Fully equipped kitchen for preparing own meals. Free WiFi. Off-street parking available.... View all property information
    Location Information
    New Haven, Connecticut 06511
    1 / 10
    Hamden
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This Royal Master Suite offers the finest set of amenities similar to those found in any luxury resort. With plenty of room to live, breathe, read, or sleep in comfort, this boudoir is truly a treat. This Colonial Home has a warm, inviting atmosphere with a hostess who is knowledgeable about... View all property information
    Location Information
    Hamden, Connecticut 06514
    1 / 12
    Branford
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Secure Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Waterfront
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    From generous picture windows enjoy views of Long Is. Sound and quaint Thimble Islands dotted with simple cottages and mansions. Large front room with a small kitchen hidden in a a 1930's armoire. A round dining table is lite from a 60" chandelier fit for a castle. Created by a professional... View all property information
    Location Information
    Branford, Connecticut 06405
    1 / 14
    Hamden
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Grill
    • Parking
    • Patio
    • Air Conditioning
    • Mountain Views
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    SAFE and convenient to all transportation and highways. This stunner has a warm, inviting atmosphere with a hostess who is knowledgeable about Connecticut AND New York City. Well appointed Colonial home with gazebo, greenhouse, open decks, and pool.<BR><BR>This former farm neighborhood promises to... View all property information
    Location Information
    Hamden, Connecticut 06514
    1 / 20
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Parking
    • Private Garden
    • Terrace
    • Washer
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy life in an authentic 1900s New England seaside village when you stay in this gorgeous two-bedroom, one-bath home. This Morris Cove corporate housing property is just 10 minutes from downtown New Haven, which means you’re close to Yale Hospital train station, Yale University, and the airport.... View all property information
    Location Information
    New Haven, Connecticut 06512
    1 / 32
    Middlefield
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Waterfront
    • Private Garden
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Clarke's Landing is newly built 2 story lakefront house with heat and air conditioning! It is a family home and has all the amenities that you would have at home.Everything is NEW! It includes cable and WiFi internet, new quality linens, paper goods, shampoo,spices, beach towels, chairs , floats... View all property information
    Location Information
    Middlefield, Connecticut 06455
    1 / 17
    Middlefield
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Parking
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful newly remodeled cottage is located on Lake Beseck in picturesque Middlefield, Ct. The views of the lake are serene and produce an immediate feeling of tranquility. This is a family home and has all the amenities that you need to feel at home including a complete kitchen. Betty's Boat... View all property information
    Location Information
    Middlefield, Connecticut 06455
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    1 / 20
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Cromwell, Connecticut 06457
    5 of 5 bubbles Reviewed 15 September 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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    1 / 10
    Branford
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Patio
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two acres of private New England charm over looking the Thimble Islands. Set atop a hill with a large rolling lawn perfect for all types of family lawn games.The vintage shingle stone home was built in 1932 for a wealthy Connecticut family. They created a sandy beach that rivals the size of the... View all property information
    Location Information
    Branford, Connecticut 06405
    1 / 15
    Branford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The building (originally a pub for local quarry workers) was built in the late 1800s, with the upper residence added in the 1930s. We've renovated the suite (2 bedrooms and 1.5 baths) with modern comforts while retaining much of the original charm. The interior design aesthetic is a blend of new... View all property information
    Location Information
    Branford, Connecticut 06405
    1 / 15
    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Magnificent, fully furnished 1st floor apartment of our 2 story home in one of the best areas of Seymour, CT. Our apartment is for non- smokers only. Very clean and calm. The apartment features a spacious living room with a 2 comfortable futon and one couch, a separate bedroom with queen size bed,... View all property information
    Location Information
    Seymour, Connecticut 06483
    1 / 11
    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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Portland, Connecticut 97201 2249
    1 / 14
    5 of 5 bubbles (1) Excellent
    Branford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Porch
    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This is a two bedroom house with a king size bed in the master bedroom and a full size in the guest bedroom. The bathroom has a jacuzzi tub and large shower. There is wi-if, cable to, a patio and all amenities. This property sleeps 4 and is PET FRIENDLY. The rental comes with private access to the... View all property information
    Location Information
    Branford, Connecticut 06405
    1 / 30
    Branford
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Stony Creek Depot is a great location: walk to the public beach, marina, playground and nature trail. The 1,000 sf Tree Fort Suite is a fun vacation retreat for a couple (with 1 or 2 kids), business travelers, academics. It's the top floor with a huge deck and access to small yard - only one... View all property information
    Location Information
    Branford, Connecticut 06405