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.

Vacation Rentals in 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.
mm/dd/yyyy mm/dd/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
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $216 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travelers get your favorite Middletown area vacation rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 20
    5 of 5 stars (1) Excellent
    Middletown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection

    The following rentals are within 15 miles of Middletown, Connecticut.

    1 / 73
    5 of 5 stars (8) Excellent
    Chester
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 20
    Farmington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    1 / 20
    Farmington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370377 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 20
    Farmington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370424 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 20
    Farmington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370406 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 20
    Farmington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370379 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 10
    Hartford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370334 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. This property with Compass Furnished Apartments gives you luxury high-rise living in... View all property information
    Location Information
    Hartford, Connecticut 06103
    1 / 10
    Hartford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370341 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. This property with Compass Furnished Apartments gives you luxury high-rise living in... View all property information
    Location Information
    Hartford, Connecticut 06103
    1 / 21
    5 of 5 stars (1) Excellent
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Grill
    • Washer
    • Balcony
    • Waterfront
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Escape to charming Lake front home with water views from virtually every room. Indoor/outdoor living at it's best with spectacular sunsets from 1500+ square feet of multi-level decks. Relax in totally renovated and professionally decorated 'home away from home' on Lake Pocotopaug. Bright and... View all property information
    Location Information
    East Hampton, Connecticut 06424
    5 of 5 stars Reviewed September 8, 2015
    We are a group of friends that like to take a week's vacation in a centrally located place and this house is perfect. It comes with all the amenities including cable and Wi-Fi...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 22
    Haddam
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Mountain Views
    • Grill
    • DVD Player
    • Balcony
    • Parking
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Located in the historic town of Haddam, Connecticut on five park-like acres surrounded by nature, The Carriage House is the perfect getaway for discriminating travelers. Newly constructed and completed in 2015, The Carriage House offers approximately 1,000 sq. ft. of luxurious living space.... View all property information
    Location Information
    Haddam, Connecticut 06438
    1 / 21
    4.5 of 5 stars (3) Very good
    East Haddam
    7 Bedrooms, Sleeps 24 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Grill
    • Waterfront
    • Washer
    • Internet Access
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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. 2017! Just 1 3/4 hours from New York or Newport RI or 2 hrs. from Boston! Canoe, kayak,... View all property information
    Location Information
    East Haddam, Connecticut 06423
    1 / 3
    Farmington
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Terrace
    • Patio
    • Air Conditioning
    • Balcony
    • Private Outdoor...
    • Porch
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Farmington, Connecticut
    1 / 20
    Farmington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370383 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 17
    4 of 5 stars (4) Very good
    East Haddam
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Hot Tub
    • Sauna
    • Washer
    • Outdoor Dining Area
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Duplex house set on twelve rolling acres on The Old Singular Farm property. Many upgrades last year. House is fresh and clean. Enjoy the deck off the back for morning coffee or join us fireside at night. We have 3 beds, one queen with a memory foam mattress and two full size beds. All have 1800... View all property information
    Location Information
    East Haddam, Connecticut 06423
    4 of 5 stars Reviewed 2 weeks ago
    Doug & Doris are very friendly, they & their adult children work the small farm everyday. Doug greeted us and took my grandson on a tour to meet the calves, chickens and pig...
    4 of 5 stars Reviewed July 6, 2016
    My daughter and 2 grandchildren traveled to CT to see my other grandson at the Goodspeed Opera House over the 4th of July weekend. Doug & Doris were extremely hospitable and...
    See all reviews
    1 / 10
    Wallingford
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Patio
    • Parking
    • Satellite TV
    • Internet Access
    • Porch
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Wallingford, Connecticut 06492
    1 / 48
    Middle Haddam
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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, badminton/volleyball court and 40' dock. A magical place to relax & recharge... Knowles Landing is one of the most beautiful waterfront estates on the... View all property information
    Location Information
    Middle Haddam, Connecticut 06456
    1 / 15
    5 of 5 stars (1) Excellent
    Haddam
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • Outdoor Dining Area
    • Parking
    • Patio
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Haddam, Connecticut 06438
    5 of 5 stars Reviewed August 20, 2015
    We were delighted with EVERYTHING about the Laurel Cottage (on the property of the Nehemiah Brainerd House B&B in Haddam)!! From the moment we arrived, the owners Maryan and...
    See all reviews
    1 / 11
    Wallingford
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Wallingford, Connecticut 06492
    1 / 11
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    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
    Get the List
    1 / 21
    East Haddam
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The Sanctuary is a mind/body retreat and wellness center situated on a 40 acre, solar-powered land preserve with a walking labyrinth, permaculture gardens, beaver ponds, forest trails, an apiary, goats and chickens. We host yoga classes, meditation, sound healings, music, and various... View all property information
    Location Information
    East Haddam, Connecticut 06423