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

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.

Downtown Elegant Stay By Yale • Rooftop • Gym
Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! With Broadway 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.

Quiet 2 bed room apt w/ private entrance.
NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

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!

Artist's Garden Apartment
Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

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
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

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.

Lakeside apartment 2.5 miles from Wesleyan campus!
Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.
Popular amenities for Middletown apartment rentals
Weekly apartment rentals

On the Park: 3 RM Apt. w/kit. in historic house

Modern Industrial Apartment with rooftop access

On The Run Farm

HideAway UConn Coventry RockFarm BnB Breakfast A+

Skylight: Cozy 2 BR, Close to Yale & Downtown NHV

Apt near Big E, Six Flags, Bradley airport

Cozy & Private Apartment Near the Ocean

King 1BR W/ Parking, Pool & Gym
Private apartment rentals

Cozy and confortable

Seasons Hospitality Cozy 1BR Waiting for you C1

Quiet Hillside Retreat | Long Stays + Fast WiFi

Lakefront Luxury on Pattagansett

The Little Chestnut.

Cozy Apartment Near Wesleyan and Town Center

Stedley Creek

Modern 1BR Near Wesleyan & Main Street
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

2BR| 1BA Sofa Bed Penthouse

cozy and Roomy

Second Floor 2Br/1Ba Minimalist Stay|Large Hot Tub
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £76 | £80 | £80 | £76 | £76 | £82 | £86 | £86 | £83 | £84 | £82 | £76 |
| 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 |
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 £23 per night before taxes and fees

Verified guest reviews
Over 3,700 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

4.7 Average rating
Middletown stays receive an average rating of 4.7 out of 5 from guests
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