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.

1 of 1 pages1 / 1
Top guest favourite
A stunning sunset paints the sky in shades of orange and pink over a calm river. The trees lining the shore provide a natural frame, while the water reflects the vibrant colors, creating a serene and picturesque scene.
Flat in Gales Ferry
4.96 out of 5 average rating, 107 reviews

Lovely Waterfront Apartment in Gales Ferry CT

We will welcome up to 2 accepted guests to a 400 sq.ft apartment. On 2.5 acres of parklike Riverfront in Gales Ferry CT., the suite is in our house but has a separate entrance. We are available for consultation yet respectful of guests' privacy. Bring your Kayak or Canoe or travel.... 20 minutes to Mystic and Mystic Seaport, 3 miles to Mohegan Sun, 7 to Foxwoods, near the Sub Base & Coast Guard Academy,& I-95. Two hours to NYC, 2 hours to Boston. Wildlife viewing from your porch/yard.

Guest favourite
A modern kitchen features sleek white cabinetry and a stone countertop. Stainless steel appliances, including a refrigerator and washer/dryer combo, are present. A large window allows natural light, while a textured area rug adds warmth to the space. Ample storage is available throughout.
Flat in Middletown
4.96 out of 5 average rating, 102 reviews

Updated 2-bedroom Near Wesleyan-Middletown

Welcome to Middletown! We are sure you will love your stay in this newly renovated apartment. This centrally located 2- bedroom apartment sleeps 4 comfortably with a large king bed in one bedroom with a TV and full bed in another. This apartment is on the second floor. Full kitchen with laundry in unit. Walk in shower in bathroom. Off street parking available. Walking distance to shops and restaurants on Main Street, Wesleyan University (1-mile walk) and Middlesex Hospital. Easy access to Rt 9

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.
Flat in Middletown
4.94 out of 5 average rating, 908 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
An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.
Flat in Milford
4.97 out of 5 average rating, 639 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

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.
Flat in New Haven
4.98 out of 5 average rating, 304 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.

Guest favourite
A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.
Flat in Southold
4.95 out of 5 average rating, 150 reviews

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Top guest favourite
A tranquil lakeside scene is captured, featuring a sandy shore beside Cedar Lake. Two benches are positioned near the water, with towels draped over them. Sunlight filters through nearby trees, creating a serene atmosphere. The calm water reflects the surrounding greenery.
Flat in Chester
4.98 out of 5 average rating, 198 reviews

Charming Chester Retreat - Cottage

*Summer's Here** Book your Cottage stay minutes from Chester's town beach: 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!

Top guest favourite
A comfortable living area is presented with a gray sectional sofa and a wooden coffee table resting on a colorful area rug. Natural light enters through large windows, illuminating the hardwood floors and revealing a small antique chest and a decorative lamp.
Flat in Deep River
4.94 out of 5 average rating, 172 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Superhost
A spacious deck is shown, offering a clear view of the Thames River and surrounding waterfront. Two light-colored lounge chairs are positioned on the deck. A series of docks and distant boats are visible on the water, with a backdrop of a partly cloudy sky.
Flat in New London
4.8 out of 5 average rating, 454 reviews

Large Waterfront Luxury Apartment

Located in Downtown Historic New London, this waterfront apartment features astounding views of the Thames River and Long Island Sound. Conveniently located, the apartment is within walking distance to restaurants, bars, galleries, the Amtrak train station and the Ferry terminals which service Block Island, Fishers Island and Long Island. The apartment also boasts a large deck overlooking the Thames with access to a grill and sitting area.

Top guest favourite
The exterior of a single-story apartment features a beige facade with brown trim. A welcoming front door is flanked by potted plants, and a covered porch is visible. Natural light illuminates the surroundings from a clear blue sky.
Flat in East Haddam
4.9 out of 5 average rating, 220 reviews

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.

Top guest favourite
The spacious attic living area features a combination of cozy seating options, including a leather couch, two upholstered chairs, and a coffee table with decorative lanterns. Natural light filters in through the windows, illuminating the warm hues of the decor. A dining table is visible in the background.
Flat in Mystic
4.96 out of 5 average rating, 107 reviews

"Meteor": River View Penthouse in Downtown Mystic

River views & salty breezes that get better with every step up from this spacious & sunny attic penthouse with private balcony freshly renovated in 2022. Whimsical boho style in open plan living walkable to all downtown Mystic amenities. Sleeps two in eco certified memory foam king with bathrobes and eye masks included for lounging & snoozing. Updated kitchen with all the mod cons, Klipsch bluetooth speaker and games in the living area.

Guest favourite
Flat in Manchester
4.97 out of 5 average rating, 148 reviews

Peaceful Pet-Friendly Retreat Near Hartford and MA

Welcome to your home away from home located steps away from downtown Manchester CT! ✔ Private entrance
✔ 1 comfortable bedroom & full bathroom
✔ Fast Wi-Fi for work and entertainment
✔ In-unit washer & dryer
✔ Complimentary coffee
✔ Pet-friendly accommodations
✔ Backyard access
✔ Quiet, residential setting Conveniently located close enough to major events but in a quaint downtown area making it prefect for short or long term stays.

Popular amenities for Middlesex County apartment rentals

Destinations to explore