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 Homes and Apartments Middletown, CT and nearby

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 17 Rentals in the Middletown Area
    loading...
    Don't let other travellers get your favourite Middletown area holiday rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 30 kilometres of Middletown, Connecticut.

    From
    $192
    / Night
    Payment Protection
    View Details
    1 / 16
    5 of 5 stars (3) Excellent
    East Hampton
    15 Bedrooms / 7 Bathrooms / Sleeps 39
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    From
    $448
    / Night
    Payment Protection
    View Details
    1 / 14
    5 of 5 stars (1) Excellent
    Guilford
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    From
    $320
    / Night
    View Details
    1 / 15
    5 of 5 stars (3) Excellent
    Guilford
    4 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Reviews (3) Make Enquiry
    From
    $1,657
    / Night
    View Details
    1 / 21
    4.5 of 5 stars (3) Very good
    East Haddam
    7 Bedrooms / 4 Bathrooms / Sleeps 21
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Ideal Connecticut location on Beautiful Crystal Clear Bashan Lake. Victorian Mansion with magnificent water views. Perfect setting for family vacations, and family reunions!! Taking reservations thru Dec. 2015! Just 1 3/4 hours from New York or Newport RI or 2 hrs. from Boston! Canoe, kayak,... View all property information
    Make Enquiry
    Location Information
    East Haddam, Connecticut 06423
    From
    $192
    / Night
    View Details
    1 / 68
    5 of 5 stars (8) Excellent
    Chester
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Connecticut Retreat was built by a pair of New Yorkers who wanted a 'spiritual and artist retreat' convenient to NYC but far from the fast-paced lifestyle of the City. The Retreat is situated on 10 wooded acres surrounded by 1000 acres of forest. Take a short walk through the woods to the... View all property information
    Make Enquiry
    Location Information
    Chester, Connecticut 06412
    5 of 5 stars Reviewed 25 September 2014
    The hosts were very easy going and combined with a clean, comfortable house in a lovely scenic location it made for a most enjoyable stay.
    5 of 5 stars Reviewed 13 July 2014
    We were in a bit of a lurch on a family getaway and needed a house due to our children (ages 3, 4 & 16) and not partial to hotels for the length of time we were there (10 nights...
    See all reviews
    From
    $358
    / Night
    Payment Protection
    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
    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
    Make Enquiry
    Location Information
    Guilford, Connecticut 06347
    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...
    See all reviews
    From
    $384
    / Night
    View Details
    1 / 15
    Haddam
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Secluded behind a stand of tall pines, the Laurel Cottage has been restored and expanded to include a full kitchen, bathroom with double pedestal bathtub and a large subway tiled shower. A cozy double brass bed in the Great Room and a luxurious pull out queen size bed on the all season porch... View all property information
    Make Enquiry
    Location Information
    Haddam, Connecticut 06438
    From
    $512
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Guilford, Connecticut 06437
    From
    $96
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Hamden, Connecticut 06514
    From
    $288
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Wallingford, Connecticut 06492
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $230
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Portland, Connecticut 97201 2249
    From
    $237
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Wallingford, Connecticut 06492
    From
    $147
    / Night
    Payment Protection
    View Details
    1 / 5
    East Haddam
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Duplex house at the Old Sindelar Farm. Everything was redone last year.Really clean. Enjoy the deck off the back or join us fireside. We have 3 beds, one queen with a memory foam mattress and two full size beds. All have 1800 count sheets so rest well. The kitchen is furnished with a blender and... View all property information
    Make Enquiry
    Location Information
    East Haddam, Connecticut 06423
    From
    $416
    / Night
    View Details
    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
    Make Enquiry
    Location Information
    Middle Haddam, Connecticut 06456
    From
    $83
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Bristol, Connecticut 06010
    From
    $1,279
    / Night
    View Details
    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
    Make Enquiry
    Location Information
    Farmington, Connecticut
    From
    $154
    / Night
    Payment Protection
    View Details
    1 / 6
    Farmington
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Located in Farmington, Ct, just 20 minutes from Hartford on Lake Dunning. Beautifully remodeled 2 bedroom condo , fully stocked and updated kitchen with granite countertops and stainless steel appliances, hardwood floors, spectacular views of the lake from the living room and master bedroom. Large... View all property information
    Make Enquiry
    Location Information
    Farmington, Connecticut 06132