
House holiday rentals in Middletown
Find and book unique houses on Airbnb
Quick stats about house rentals in Middletown

Total holiday rentals
Explore 60 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at €35 per night before taxes and fees

Verified guest reviews
Over 2,120 verified reviews to help you choose

Family-friendly holiday rentals
30 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
60 of Middletown holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middletown rentals

4.9 Average rating
Middletown stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated house rentals in Middletown
Guests agree: these houses are highly rated for location, cleanliness and more.

Family Stays, CT
Centrally located - just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and generous space for groups. With 4 bedrooms across two floors, the layout lets everyone spread out. Bedrooms on separate levels provide natural privacy while still enjoying one shared home. Whether you're traveling with friends, children, extended family, or multiple couples, the 2‑floor setup helps everyone relax without feeling crowded. Ideal for multi‑generational stays and group getaways.
4.99 out of 5 average rating, 145 reviews
Beautiful lakefront home, 4bed 2.5ba
80ft of lakefront. Perfect for summer water activities, stunning fall foliage and ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room & wood-burning stove, dining room and 1/2 bath. Large porch faces lake, with sitting area and dining table. Ground floor king-size master & bathroom, with stunning lake views. Upstairs 3 queen bedrooms, all w lake views and ample closet space. TVs in 3 bedrooms + projector/screen for movie watching.
4.86 out of 5 average rating, 147 reviews
Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.
4.93 out of 5 average rating, 354 reviews
Prime West Hartford Center Location: Historic Gem
With over 500 five star guest reviews, Mark Chu Rentals is known for exceptional hospitality, thoughtful details, and memorable stays. Enjoy the perfect blend of historic charm and modern comfort in the heart of West Hartford Center. Relax on the spacious private deck with a gas fire pit and grill, or take a short walk to Blue Back Square for boutique shopping, restaurants, cafés, and entertainment. The nearby Delamar Hotel makes this an ideal location for business and leisure travelers alike.
4.98 out of 5 average rating, 121 reviews
The Dragon Fly Garden
The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet
4.8 out of 5 average rating, 147 reviews
Bright & Private WHOLE HOUSE 4 YOU Near Everything
Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)
4.95 out of 5 average rating, 119 reviews
Beautiful Lake House on Lake Pocotopaug
Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.
4.89 out of 5 average rating, 114 reviews
Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!
4.99 out of 5 average rating, 162 reviews
Charming Cape Home, Close to All
Charming Cape Home in the Heart of Connecticut Enjoy comfort and convenience just 20 mins from Bradley Airport, 10 mins from Hartford, 25 mins from UConn, and 40 mins from New Haven. Nestled on a quiet residential street, our cozy home features multiple beds, fast Wi-Fi, Smart TVs, central air, and a fenced backyard with patio and fire pit. Grocery stores, restaurants, and coffee shops are just 5 minutes away. A perfect retreat for families, professionals, or campus visits!
4.9 out of 5 average rating, 115 reviews
Relax by the water in a 4 bedroom house
Relax with the whole family at this recently renovated, spacious 4 bedroom house on Beaver Pond. Centrally located in the crossroads of Connecticut and a short train ride away from NYC, come relax by the water in a quiet neighborhood setting. Stay home and enjoy a kayak or canoe on the pond or visit the many nearby attractions like mini golf, skiing, hiking or the rest that Connecticut has to offer. The home has been recently remodeled and has a very spacious yard.
4.82 out of 5 average rating, 141 reviews
Cozy Family Home - Kid & Pet Friendly
3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.
4.92 out of 5 average rating, 237 reviews
Quiet Comfy Getaway 3 BR Home | Close to BDL
Welcome to our newly renovated 3-bedroom home in Windsor, CT! Sleeps up to 8 guests and is perfect for families, business travelers, healthcare professionals, and extended stays. Enjoy fast WiFi, a dedicated workspace, fully equipped kitchen, complimentary coffee bar, washer/dryer, free parking, and spacious bedrooms. Minutes from Hartford, Bradley Airport (BDL), hospitals, shopping, dining, and major highways.
4.94 out of 5 average rating, 122 reviewsPopular amenities for house rentals in Middletown
House rentals with a pool

Breathtaking home with unforgettable views & pool!
4.92 out of 5 average rating, 131 reviews
Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
4.88 out of 5 average rating, 129 reviews
Stunning Views, Bucolic Bliss in 1790s Farmhouse
4.93 out of 5 average rating, 212 reviews
Cozy Waterfront Home w/Hot Tub ~ Connecticut River
4.97 out of 5 average rating, 89 reviews
Killingworth Estate - Elite Amenities & Finishings
4.95 out of 5 average rating, 40 reviews
Country getaway - pool, huge yard,
4.97 out of 5 average rating, 87 reviews
Family Retreat Near Hartford – Year-Round Getaway
4.97 out of 5 average rating, 35 reviews
15 acres! * Pine Pond at Devils Hopyard State Park
5.0 out of 5 average rating, 48 reviewsWeekly house rentals

Luxe Bolton Lake
4.99 out of 5 average rating, 186 reviews
Renovated Single Family Home in Central CT
5.0 out of 5 average rating, 15 reviews
CT River Retreat - Modern Home with CT River Views
5.0 out of 5 average rating, 68 reviews
Cozy Family Home-Sleeps 6 Near Wesleyan & Weddings
5.0 out of 5 average rating, 8 reviews
Historic Connecticut Country House Retreat
4.94 out of 5 average rating, 16 reviews
Hilltop A-frame retreat
4.75 out of 5 average rating, 4 reviews
Cozy Colonial House | Centrally Located
4.77 out of 5 average rating, 92 reviews
Quarry House: Mid-Century Modern
5.0 out of 5 average rating, 24 reviewsPrivate house rentals

Guilford Field House
5.0 out of 5 average rating, 38 reviews
Lovely, peaceful lakefront home.
5.0 out of 5 average rating, 16 reviews
Charming River Home
4.82 out of 5 average rating, 50 reviews
Urban Luxury in Central CT w/ free RV parking
5.0 out of 5 average rating, 94 reviews
Waterfront Lake House
4.83 out of 5 average rating, 77 reviews
East Haddam Village | Walkable, Pet Friendly
4.9 out of 5 average rating, 58 reviews
Waterfront Property on 30 Acres
4.98 out of 5 average rating, 63 reviews
Fun on the Lake: Games, Dock, Slide, EV Charger
4.99 out of 5 average rating, 85 reviewsWhen is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €116 | €129 | €150 | €148 | €151 | €143 | €145 | €142 | €122 | €120 | €108 | €115 |
| 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
- Thunder Ridge Ski Area
- Ocean Beach Park
- Mystic Seaport Museum
- Mystic Aquarium
- University of Connecticut
- Kent Falls State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Compo Beach
- 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





