Apartment holiday rentals in Middletown

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Top-rated apartment rentals in Middletown

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Guest favourite
A stylish living area features a brown leather sofa, surrounded by windows that provide ample natural light. Decorative elements include vibrant throw pillows, a patterned rug, and an artwork piece on the wall. A wooden dining table complements the space while a sleek television is positioned nearby.
Apartment in Downtown Hartford
4.9 out of 5 average rating, 102 reviews

Designer's Den in the Business District

The Quintessential Hartford Experience!! Historic building in the heart of Hartford's Business District makes the "Designer's Den" a truly unique city-living experience. Big city vibes in a stylish corner unit with views of the Capital building & Bushnell Park. The unit is very nicely appointed with all the creature comforts you can imagine (+blackout curtains) . The Elevator makes grocery-hauling in the city easy. Located within walking distance of the very best downtown Hartford has to offer!

Top Guest favourite
Apartment in Chester
4.98 out of 5 average rating, 190 reviews

Charming Chester Retreat - Cottage

*Winter's Here** Book your Cozy New England Cottage stay : This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also includes a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Beach Access 10 min away at Cedar Lake. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! Hidden Gem / Retreat/ Beach Access

Top Guest favourite
A bright living space is showcased with wooden floors and white walls. A dark leather sofa faces a wooden coffee table, while a rocking chair invites relaxation. A dining area features a table with four orange chairs, complemented by natural light from nearby windows.
Apartment in Middletown
4.94 out of 5 average rating, 868 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Top Guest favourite
A peaceful view of Paper Goods Pond is captured, showcasing calm waters reflecting the sky. Surrounding trees display vibrant autumn colors, and a grassy area leads down to the water's edge. The serene landscape provides a backdrop for relaxation and connection with nature.
Apartment in Berlin
4.91 out of 5 average rating, 109 reviews

Pond View Retreat I in Central CT

Comfortable 1 bedroom apt. Centrally located between Hartford and New Haven Near CCSU, UCONN Medical, HOCC, Hartford, Middletown. Perfect for extended stay. Business, nurses, snowbirds. We host short term if available close to requested dates. Separate one bedroom apts. 2nd floor. Washer/Dryer. See our 2nd listing Pond View Retreat II. Clean, safe location. Close to train station, banks, restaurants, grocery stores ,hwy. Relax and enjoy the four seasons over looking Paper Goods Pond!

Top Guest favourite
A cozy living space features a light-colored sofa with yellow accents, positioned beside a small round table. A striped area rug adds texture to the hardwood floor. Bright natural light enters through nearby windows, illuminating the space and connecting to the kitchen and bathroom beyond.
Apartment in Dwight
4.98 out of 5 average rating, 266 reviews

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

Superhost
A well-appointed sleeping area features a spacious bed with crisp white linens and decorative pillows. Two comfortable chairs are positioned around a circular table, complemented by a potted plant and a cozy blanket draped over one chair. Large windows allow natural light to fill the room.
Apartment in Downtown Hartford
4.89 out of 5 average rating, 218 reviews

Executive Stay Downtown Hartford

Enjoy a perfect upscale and stylish experience at this centrally located stay in downtown Hartford. With beautiful views of downtown Hartford overlooking our central park known as "The Green", this unit has everything you need (+blackout curtains) . This is Immediately across the street from the XL Center, home of our UCONN HUSKIES, and a short, quick walk from the executive buildings. Come enjoy an amazing stay at one of the premier locations in the city. (Also includes easy parking access.)

Top Guest favourite
A spacious living area features high wooden ceilings and large windows allowing natural light to fill the room. A black sofa and stylish chairs surround a round dining table. A television is positioned on the wall, accompanied by decorative plants and neutral-toned artwork.
Apartment in Torrington
4.96 out of 5 average rating, 259 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Top Guest favourite
A claw-foot tub is positioned in front of a large window, surrounded by potted plants and natural light. The setting features a textured stone floor and a cozy stool, creating a serene bathing space with a touch of elegance.
Apartment in Fair Haven
4.98 out of 5 average rating, 297 reviews

The Pearl, New Haven

Amazing hidden luxury experience along the Quinnipiac River in a historic mid-19th century property. Enjoy the scenic river and sunset views, soak in our stunner claw-foot tub, recharge in the sunlit living room, work in the dining alcove, or relax by the bay windows with your favorite drink. NO KITCHEN, but we have a coffee maker, tea kettle, toaster oven, microwave, fridge, plates, and cutlery. We are 15 mins drive from Yale, 2 mins walk to the downtown bus, and easy cycling downtown.

Guest favourite
Apartment in Wallingford
4.94 out of 5 average rating, 102 reviews

Sweet Sparkling Clean Boho 1 bedroom

One bedroom, 3rd story apartment, completely separate, with its own entrance. Comes with a single off street parking space. Centrally located in downtown Wallingford. Close to shops, restaurants and bars. Also within a couple of miles of the Toyota Oakdale Theatre. If you are looking for a place to come and party for the night, this is not a good space for you. This is a quiet building with the landlord on premise. No pets.

Top Guest favourite
Apartment in New Britain
4.96 out of 5 average rating, 250 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Guest favourite
The exterior of Lori Warner Studio/Gallery showcases a vibrant red door framed by large glass windows. A deep blue awning offers shade, while decorative planters with greenery are positioned beside the entrance. Outdoor seating is visible in the background, complementing the inviting atmosphere.
Apartment in Chester
4.91 out of 5 average rating, 411 reviews

Chester Village 'Pied-à-terre' above art gallery

Our lovely apartment is well designed in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!

Top Guest favourite
The welcoming exterior of a classic two-story home is showcased, featuring dark siding and white shutters. A well-maintained pathway leads to the entrance, illuminated by a lamp post. Rocking chairs are visible on the porch, with light spilling from the windows, suggesting a cozy atmosphere.
Apartment in Wallingford
4.96 out of 5 average rating, 401 reviews

Spacious in-law apartment steps from Choate

Private apartment with private entrance. This cute apartment is located in the center of town, close to Choate Rosemary Hall and downtown Wallingford. Very safe and charming neighborhood. Off street parking included. The private space includes a combination living, dining room, and full kitchen. Private bathroom with clean shower and amenities. Beautiful backyard with a pretty patio

Popular amenities for Middletown apartment rentals

When is the best time to visit Middletown?

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Quick stats about apartment rentals in Middletown

  • Total holiday rentals

    Explore 40 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,630 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Middletown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Middletown rentals

  • 4.8 Average rating

    Middletown stays are highly rated by guests—averaging 4.8 out of 5!