
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 $39 SGD 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.

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

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.

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!

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!

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.

On The Run Farm
Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

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.

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.

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

1R Private Downtown Oasis
Private First Floor Rear Apartment of an 1849 historical home in the heart of Middletown, CT. One block walk to Wesleyan University with private parking. Main street also one block away with many great restaurants, and our best local coffee shop (Klekolo) just doors away from your apartment. The House is across from the public library. Stone patio in a lovely fenced in rear yard.
Popular amenities for Middletown apartment rentals
Weekly apartment rentals

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

Wallingford Getaway

Soaking Tub Retreat | Cozy Luxe Stay Near Yale

HideAway UConn Coventry RockFarm BnB Breakfast A+

Private 1 bedroom apartment in central Connecticut

Cozy studio loft

Pond View Retreat I in Central CT

The Overlook...HOST & Co.
Private apartment rentals

Quiet Hillside Retreat | Long Stays + Fast WiFi

Private Apartment I Near Wesleyan University

The Little Chestnut: Walk to downtown Chester.

Cozy Apartment Near Wesleyan and Town Center

The Farmhouse Loft Guesthouse

Central Town 1BR Furnished Apt - Prime Location

Peaceful Farm Country Getaway

Entire condo for the perfect getaway!
Apartment rentals with a hot tub

West River Gem.

Near Tweed, Yale & The Estate, Mins to Downtown

Rural retreat in Colebrook CT

Kyles and Bryans oasis

Cozy Studio: Indoor Hot Tub & Inground Pool Access

cozy and Roomy

Second Floor 2Br/1Ba Minimalist Stay|Large Hot Tub

1ST FLR APT Your private resort, now FAMILY-ized!
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $129 SGD | $136 SGD | $136 SGD | $129 SGD | $129 SGD | $139 SGD | $146 SGD | $146 SGD | $141 SGD | $143 SGD | $139 SGD | $129 SGD |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Destinations to explore
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- Flat rentals Connecticut
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Six Flags New England
- Fairfield Beach
- Thunder Ridge Ski Area
- Ocean Beach Park
- Mystic Seaport Museum
- Mystic Aquarium
- Kent Falls State Park
- University of Connecticut
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- Sleeping Giant State Park
- Yale University Art Gallery
- Sherwood Island State Park
- Wölffer Estate Vineyard
- Ski Sundown
- Ocean Beach
- Long Island Aquarium





