
Apartment holiday rentals in Middlesex County
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Middlesex County
Guests agree: these apartments are highly rated for location, cleanliness and more.

The Federal Suite at the Wisteria Rest
The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

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.

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.

Charming Chester Retreat - Cottage
*Winter's Here** Book your Cozy New England Cottage Now : 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

The Millhouse Downtown Chester
An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

One bedroom newly renovated clean and quiet. Apt F
Your home away from home. Queen size bed. End unit facing the woods in a quiet 6 unit apartment building. Off street parking. Pay laundry. Food shopping only a 2 minute walk for that emergency ice cream fix or last minute beverage. 5 minute drive to romantic Willimantic and 15 to Norwich. Casinos are 25 minutes away. All appliances are brand new as of 1/20/21. Glass top stove, fridge, microwave and dishwasher. Tile wood and carpet are also new and has central heat and air conditioning.

Downtown Branford Retreat - Quiet yet Central Apt
A welcoming apartment nestled in the heart of Branford - a quintessential shoreline community! This inviting space offers modern design, a well-equipped kitchen, comfortable bedroom, and a convenient location. Situated within walking distance of the town green and minutes from beaches, guests can easily explore this vibrant shoreline town. From boutique shops and art galleries to charming cafes and trendy restaurants, experience the best of Branford right at your doorstep!

Penny Corner Airbnb
My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

The Winchester House at Science Park-Yale
Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

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.

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!

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 Middlesex County apartment rentals
Weekly apartment rentals

The Stern at Soundview · Beach+Ocean+Sunrise

Life on the Farm

Cozy Private Lake Q Retreat

The Little Chestnut: Storybook Stay in the Village

Cozy Shoreline Getaway

Cozy Apartment Near Wesleyan and Town Center

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

In-law Private Studio Apartment
Private apartment rentals

Betty’s Brickhouse-ask about shorter stays

Designer's Den in the Business District

Tide Unit- Charming Furnished Boutique 1BR

Private apartment in historic Old Lyme mansion

Premium convenient stays

Upscale Mystic Apartment 7 min Walk to Drawbridge

⭐ Modern Studio in Heart of Downtown Mystic

Guilford Guest House- private studio apartment
Apartment rentals with a hot tub

Luxury Penthouse Minutes to Yale

The Cozy Corner

1 Bedroom Sleep4 Waters Edge Resort Jan-March Deal

Cozy Corner, by the Spa

Relaxing Getaway at the Norwich Inn and Spa Villas

Garden Suite: Private Full Apartment

Chalet Tré

Serene Escape: Sauna, Hot Tub & Nearby Beaches
Destinations to explore
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- Family-friendly rentals Middlesex County
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- Beachfront rentals Middlesex County
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- Rentals with lake access Middlesex County
- Rentals with beach access Middlesex County
- Rentals with a patio Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Private suite rentals Middlesex County
- Rentals with a firepit Middlesex County
- Bed and breakfasts Middlesex County
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- House rentals Middlesex County
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- Flat rentals Connecticut
- Flat rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- East Matunuck State Beach
- Long Island Aquarium
- Hammonasset Beach State Park
- Mystic Seaport Museum
- Mount Southington Ski Area
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Burlingame State Park
- Yale University Art Gallery
- Ski Sundown
- Orient Beach State Park
- East Hampton Main Beach
- Meschutt Beach
- Wölffer Estate Vineyard
- Bluff Point State Park




