We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals and Homes in Cheshire, CT

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 20 Rentals in the Cheshire Area
    loading...
    Don't let other travellers get your favourite Cheshire area holiday rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 30 kilometers of Cheshire, Connecticut.

    From
    €118
    Per Night
    View Details
    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
    From
    €255
    Per Night
    View Details
    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
    From
    €269
    Per Night
    View Details
    1 / 12
    Branford
    Studio / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    From
    €910
    Per Night
    View Details
    1 / 10
    Branford
    5 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Air Conditioning
    • Fireplace
    • Water Views
    • Private Fishing...
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Branford, Connecticut 06405
    From
    €168
    Per Night
    View Details
    1 / 10
    Wallingford
    1 Bedroom / 2 Bathrooms / Sleeps 2
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Linens Provided
    • Air Conditioning
    • Deck
    • Porch
    • Satellite TV
    • Internet Access
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wallingford, Connecticut 06492
    From
    €455
    Per Week
    View Details
    1 / 14
    Hamden
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Stereo System
    • Deck
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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. This former farm neighborhood promises to... View all property information
    Make Enquiry
    Location Information
    Hamden, Connecticut 06514
    From
    €145
    Per Night
    View Details
    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
    • Washer
    • Internet Access
    • Refrigerator
    • Mountain Views
    • Patio
    • Dryer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Southbury, Connecticut 06488
    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...
    See all reviews
    From
    €819
    Per Night
    View Details
    1 / 16
    Bethlehem
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Private Tennis Court
    • Fireplace
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Bethlehem, Connecticut 06751
    From
    €205
    Per Night
    View Details
    1 / 11
    Wallingford
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Wallingford, Connecticut 06492
    From
    €319
    Per Night
    View Details
    1 / 14
    5 of 5 stars (1) Excellent
    Guilford
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Fireplace
    • Deck
    • Air Conditioning
    • Waterfront
    • Water Views
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Create memories of an unforgettable vacation in this lake house with direct access to a private dock and boats. Our house features top of the line GE Monogram kitchen appliances, latest model 50' HDTV, 70 Mb/sec Wi-Fi internet, Sony PlayStation 3 with a collection of best games, and absolutely... View all property information
    Make Enquiry
    Location Information
    Guilford, Connecticut 06437
    5 of 5 stars Reviewed 29 August 2014
    Booked by friends, we had a stay here for 3 nights. We wished we had had longer. House is of a VERY high standard, with top quality appliances, kitchen and bathrooms. Very clean...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    €123
    Per Night
    View Details
    1 / 20
    Middletown
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • TV
    • Stereo System
    • Hot Tub
    • There Are Tennis...
    • Watersports Nearby
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Make Enquiry
    Location Information
    Middletown, Connecticut 06457
    From
    €164
    Per Night
    View Details
    1 / 10
    New Haven
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • TV
    • Elevator/Lift access
    • DVD Player
    • Gym
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Compass Furnished Apartments at 360 State Street gives you what you’ve been looking for. 360 State Street is the second-tallest building in New Haven with 700,000 square-feet of “green” living. Our beautifully furnished apartments include oversized windows with beautiful views, Energy Star... View all property information
    Make Enquiry
    Location Information
    New Haven, Connecticut 06510
    From
    €227
    Per Night
    View Details
    1 / 32
    New Haven
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Skiing: Property Is...
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • TV
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Unique 2500sf 4 br, 2.5 bath Home on the Quinnipiac river just 5-10 minute drive to downtown New Haven and Yale. on the bus line. Master suite with steam shower, laundry big private yard with Hot tub, River view porch, directly next to park. 1890 victorian on the Quinnipiac river with all the New... View all property information
    Make Enquiry
    Location Information
    New Haven, Connecticut 06513
    From
    €2,276
    Per Week
    View Details
    1 / 5
    Branford
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Private Fishing...
    • Horse Riding Nearby
    • Water Views
    • Washer
    • Wi-Fi
    • Dryer
    • Watersports Nearby
    • There Are Tennis...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    In the charming and quirky former fishing and oystering village of Stony Creek, CT right on Long Island Sound, our beloved salt box style house from the 1850's offers you 2,200 sq.feet of living space. It is located between Branford and Guilford, two dignified old New England towns. Take the time... View all property information
    Make Enquiry
    Location Information
    Branford, Connecticut 06405
    From
    €164
    Per Night
    View Details
    1 / 11
    Portland
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Shared Tennis Court
    • Internet Access
    • Air Conditioning
    • TV
    • Elevator/Lift access
    • Mountain Views
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Enquiry
    Location Information
    Portland, Connecticut 97201 2249
    From
    €364
    Per Night
    View Details
    1 / 9
    Guilford
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Waterfront
    • Watersports Nearby
    • DVD Player
    • Ocean Views
    • Central Heating
    • TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Guilford, Connecticut 06437
    From
    €101
    Per Night
    View Details
    1 / 19
    5 of 5 stars (6) Excellent
    New Haven
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Water Views
    • Boat Available
    • Stereo System
    • Water Park Nearby
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    New Haven, Connecticut 06512
    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...
    See all reviews
    From
    €228
    Per Night
    View Details
    1 / 15
    5 of 5 stars (3) Excellent
    Guilford
    4 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Grill
    • Fireplace
    • Private Fishing...
    • Stereo System
    • Ocean Views
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Guilford, Connecticut 06437
    5 of 5 stars Reviewed 20 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...
    See all reviews
    From
    €341
    Per Night
    View Details
    1 / 39
    Middle Haddam
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Stereo System
    • Waterfront
    • Boat Available
    • Internet Access
    • DVD Player
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Middle Haddam, Connecticut 06456
    From
    €910
    Per Night
    View Details
    1 / 3
    Farmington
    6 Bedrooms / 8 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Deck
    • Air Conditioning
    • Fireplace
    • Private Outdoor...
    • Patio
    • Garage
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Farmington, Connecticut
    Get the List