Apartment holiday rentals in Middletown

Find and book unique apartments on Airbnb

Quick stats about flat rentals in Middletown

  • Total holiday rentals

    Explore 40 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 3,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Middletown holiday rentals include wifi 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!

Top-rated apartment rentals in Middletown

Guests agree: these apartments are highly rated for location, cleanliness and more.

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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, 917 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.

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, 105 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

Guest favourite
Flat in Hartford
4.89 out of 5 average rating, 172 reviews

Signature Bloom # 54

Located in the Westend of Hartford near the West Hartford town line, minutes from Downtown Hartford, Convention Center, XfinityTheatre and local Hospitals. Come join us in your travels and let us accommodate your needs with personal touches. We offer a comfortable experience designed to meet your personal or business needs. Please enjoy our continental breakfast and fully equipped popcorn maker at your convenience! Signature Bloom🌱 HOSPITALITY IS our business… One Guest at a time

Top guest favourite
A bright living space is depicted with light wooden flooring. A cozy seating area features a blue sofa facing a simple white table. Behind the table, a wooden dining set with four chairs is visible. Shelves with decor adorn the walls, and a kitchen area can be seen in the background.
Flat in New Haven
4.94 out of 5 average rating, 180 reviews

Elegant Modern Stay Near Yale • Gym • Roof Terrace

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! Broadway lies just around the corner and some of New Haven’s best Pizza a stone’s throw away you’d be hard-pressed to find a better location for your stay. Enjoy cooking up a nice dinner at home one night using the fully-equipped kitchen provided. Spend the evening on the rooftop terrace watching the sunset over the city skyline before tucking in for the night. Use the downstairs gym for a morning workout.

Superhost
A bright living area features large windows, allowing natural light to fill the space. A comfortable gray sofa sits alongside a round coffee table and a cozy armchair. The open kitchen is equipped with modern appliances and sleek cabinetry, ideal for a relaxing stay.
Flat in New Haven
4.95 out of 5 average rating, 124 reviews

Luxurious 3BR Apartment w/ Parking & Gym

Our prime location meets modern elegance. This three-bedroom spacious apartment is designed for comfort, convenience, and sophistication in the heart of a dynamic urban community. Whether planning a quiet night in or a lively evening downtown, Hyatus amenities elevate your living experience. º Rooftop Sky Lounge with an outdoor TV º Screening area º Cabanas º Billiards º Bocce courts º Fireside lounge º Co-working space featuring private work pods º Meeting rooms º Cappuccino Bar

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, 173 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.

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
4.88 out of 5 average rating, 225 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
Flat in Manchester
4.97 out of 5 average rating, 153 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.

Top guest favourite
Flat in New Britain
4.95 out of 5 average rating, 287 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.
Flat in Chester
4.91 out of 5 average rating, 432 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.
Flat in Wallingford
4.96 out of 5 average rating, 420 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

Guest favourite
A spacious living area features large windows allowing natural light to fill the room. A sectional sofa and armchair are arranged around a decorative rug. A television is positioned on a wooden cabinet, and a plant adds a touch of greenery to the decor.
Flat in East Rock
4.93 out of 5 average rating, 135 reviews

Apartment in New Haven

This is a luxurious and spacious apartment on the ground floor of a historic home, centrally located in the heart of East Rock. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The master bedroom has a king bed and a private shower/bathroom. The guest bedroom has a queen bed and library.

Popular amenities for Middletown apartment rentals

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