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Vacation Rentals in Cheshire, CT and nearby

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    All 21 Rentals in the Cheshire Area
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    The following rentals are within 30 kilometres of Cheshire, Connecticut.

    From
    $426
    / Night
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    1 / 14
    5 of 5 stars (1) Excellent
    Guilford
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    From
    $487
    / Night
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    1 / 22
    5 of 5 stars (2) Excellent
    New Haven
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Enquiry
    From
    $304
    / Night
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    1 / 15
    5 of 5 stars (2) Excellent
    Woodbury
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    From
    $158
    / Night
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    1 / 17
    5 of 5 stars (11) Excellent
    Branford
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This newly renovated one bedroom cottage is set in the midst of other cottages. With a private back garden, patio, beautiful flowers, and steps from a private neighborhood beach , the cottage is clean, and comfortable. For cool nights there is a gas fire, and an air conditioner in the bedroom... View all property information
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    5 of 5 stars Reviewed 3 August 2014
    Last January we had set our eyes on the Ennis Cottage for the last two weeks of July and the long wait was worth it. For spending a holiday there is like uncorking your first...
    5 of 5 stars Reviewed 21 April 2013
    We had a very pleasant stay at the Ennis Cottage. The warm welcome we felt with Ron and his help getting around in and near Branford made us feel home and looking forward to...
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    From
    $193
    / Night
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    1 / 27
    5 of 5 stars (1) Excellent
    Southbury
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Charming, recently renovated, two-story, 1,200 square-foot coach house built in 1795 and set in a tranquil 3-acres of lawns, gardens, orchards and forest at the heart of the historic Village of South Britain founded in 1715 by settlers from the south of England, This vacation home an hour and a... View all property information
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    5 of 5 stars Reviewed 7 January 2015
    My husband and I, and our doggies, enjoyed the Coach House so much. We became friends with the owner who was very accomodating. He even loaned us his ornaments, so we could...
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    From
    $341
    / Night
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    1 / 38
    3 of 5 stars (1) Average
    Guilford
    2 Bedrooms / 1 Bathroom / Sleeps 6
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    we have over 30 POSITIVE REVEIWS ON HOMEAWAY 'We had a wonderful time at this lovely home in Guilford. We found the home to be cozy, comfortable and beautifully decorated. We will definitely stay here again in the future. We loved being able to walk to town to the Green, shoppes, restaurants, etc.... View all property information
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    3 of 5 stars Reviewed 8 December 2014
    The house is in a great location and has good bones. It was generally what we needed, though it lacked some basic things like sheets that fit the bed and bath towels. Some basic...
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    From
    $359
    / Night
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    1 / 12
    Branford
    Studio / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
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    From
    $225
    / Night
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    1 / 10
    Wallingford
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Welcome to The Wallingford Victorian Inn We are a B&B The room rate posted is for one suite that will sleep 2 We have 5 suites available for rental if your party is larger The rate is per suite per night The Wallingford Victorian Inn regally presides over the corners of North Main Street and... View all property information
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    From
    $1,095
    / Night
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    1 / 16
    Bethlehem
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All... View all property information
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    From
    $487
    / Night
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    1 / 9
    Guilford
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Ocean Views
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    LittleNeck cottage is located on Island Bay in historic Guilford, CT. Only 2 miles to quaint, picturesque town green and harbor., one mile to Stony Creek and Thimble Islands. Twenty minutes to New Haven and Yale University. Convenient to Mohegan Sun and Foxwoods Casinos, Mystic Seaport, Outlet... View all property information
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    From
    $61
    / Night
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    1 / 15
    Plymouth
    8 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This beatuiful 8 room Raised Ranch is located on a quiet dead end street. Home is very spacious with a new efficient oil based heating system. Large eat in kitchen with appliances. Large dining room with sliders to two tier deck overlooking a 1 acre lot. Living room is large with fireplace.... View all property information
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    From
    $943
    / Night
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    1 / 3
    Milford
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    4 bedroom, 3 full bathroom , Beach house, directly on the water View all property information
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    From
    $91
    / Night
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    1 / 20
    Hamden
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • x
    About this property
    Beautiful, modern, clean, SAFE, comfortable, and convenient to all transportation and highways. This stunner has a warm, inviting atmosphere with a hostess who is knowledgable about Connecticut AND New York City. The rental is a HIP, bright, basement apartment in a well appointed Colonial style... View all property information
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    From
    $219
    / Night
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    1 / 11
    Portland
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    From
    $274
    / Night
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    1 / 11
    Wallingford
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Brae Cottage is an elegantly designed small home. It sits in an open field, next to woods and overlooking a pond. There is a large living room with cathedral ceiling and fireplace. The living room opens onto a covered terrace and includes a queen sized Murphy Bed. There is fully equipped kitchen &... View all property information
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    From
    $79
    / Night
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    1 / 7
    Bristol
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Located in 1880 home in older quiet neighborhood .Nearby park to walk in. Located 2 miles from ESPN and the great Lake Compounce amusement park. Walking distance to clock museum, shopping, library and churches. Short drive to carousel museum. 13 miles from capital of Hartford. Off street... View all property information
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    From
    $1,216
    / Night
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    1 / 10
    Branford
    5 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    From
    $304
    / Night
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    1 / 15
    5 of 5 stars (3) Excellent
    Guilford
    4 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Ocean Views
    • Private Fishing...
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    We love our cottage and you will too! 'Seacliff,' a classic turn of the century cedar shingled beach cottage, is located in the quiet Guilford, CT community of Mulberry Point. Direct water access for swimming, beachcombing, kayaking and fishing plus family-friendly association beach within a... View all property information
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    5 of 5 stars Reviewed 19 September 2014
    If you are looking for an almost indescribably beautiful setting and a rustic, relaxing location, Seacliff is it. The view from the front screen porch and terrace is nothing short...
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    From
    $135
    / Night
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    1 / 19
    5 of 5 stars (6) Excellent
    New Haven
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Charming beach cottage, clean, well maintained interior,central AC. Cottage located on dead end street, 4 houses from LI Sound. Residents share PRIVATE BEACH.Guests of property also have beach rights to adjacent PRIVATE BEACH. View of ocean and salt marsh from front porch. Short walk to TOWN BEACH... View all property information
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    4 of 5 stars Reviewed 5 December 2014
    This is a well equipped and furnished property. It was very clean and comfortable and WiFi and telephone were included. The house is only a few yards from the beach and, for...
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    From
    $395
    / Night
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    1 / 39
    Middle Haddam
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Captain's House, a 3,400 SF 3-level renovated waterfront Victorian, features 5 bedrooms, 3-1/2 baths, gourmet kitchen,wraparound deck, tennis court and 40' dock. A magical place to relax & recharge... Knowles Landing is one of the most beautiful waterfront estates on the Connecticut River.... View all property information
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    From
    $1,216
    / Night
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    1 / 3
    Farmington
    6 Bedrooms / 8 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Fireplace
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    magnificant French Normandy hillside all brick 6 bedroom 7.5 bath custom Mansion with 3.5 acres beautiful, lush, private, exclusive ESTATE, in prestigious FARMINGTON, CT. Just at I-84, Exit 39. May be leased for long weekends, weekly or long term stay. . 6 bedrooms, 7.5 baths, swimming pool,... View all property information
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