
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.

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.

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

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

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.

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

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.

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

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
Weekly apartment rentals

Charming Chester Retreat - Cottage

Water front studio apartment with fireplace.

Ensign House Room

Wallingford Getaway

Quiet 2 bed room apt w/ private entrance.

The Pearl, New Haven

Cozy Apartment Centrally Located in Southbury

Private Apartment I Near Wesleyan University
Private apartment rentals

Walk To Goodspeed Opera House!

Central Town 1BR Furnished Apt - Prime Location

Cozy and confortable

The Little Chestnut: Walk to downtown Chester.

West Hartford Center: Charming New England Apt

Peaceful Farm Country Getaway

Former train depot on the river.

The Italianate Oasis Luxury Stay West End Hartford
Apartment rentals with a hot tub

Cozy Studio: Indoor Hot Tub & Inground Pool Access

1st floor Apt. Your private resort, Family-sized!

Rural retreat in Colebrook CT

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

Shoreline Fun for all Seasons

Near Tweed, Yale & The Estate, Mins to Downtown

West River Gem.

Cozy 3 BR Retreat w/ Jacuzzi, Office +Backyard.
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €86 | €90 | €90 | €97 | €100 | €102 | €97 | €97 | €94 | €95 | €93 | €86 |
| 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
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Thunder Ridge Ski Area
- Mystic Seaport Museum
- Mystic Aquarium
- University of Connecticut
- Kent Falls State Park
- Soundview Beach
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Sherwood Island State Park
- Ski Sundown
- Orient Beach State Park
- Meschutt Beach





