Holiday rentals in Middletown

5 out of 5 average rating, 43 reviews

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

4.94 out of 5 average rating, 803 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.

4.93 out of 5 average rating, 141 reviews

Guest suite in Cheshire

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

Superhost

4.8 out of 5 average rating, 51 reviews

Cozy Apartment Near Wesleyan and Town Center

Our home is located within minutes of downtown Middletown. You can eat in our well equipped kitchen or out at any of the 5 star restaurants around town. Enjoy hopping into small boutique and major big box stores around town. Parents of Wesleyan students can enjoy visiting and come stay in a quiet apartment minutes from the campus. There are art galleries, summer theatre nearby and a nice safe place to stroll around town. If hiking is your thing, there are many marked trails around the area.

5 out of 5 average rating, 200 reviews

Guest house in Portland

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

5 out of 5 average rating, 125 reviews

Home in Haddam

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!

4.94 out of 5 average rating, 154 reviews

Apartment in Middletown

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kitchen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

4.95 out of 5 average rating, 191 reviews

Flat in New Britain

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 suite in Wallingford

5 out of 5 average rating, 591 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

4.88 out of 5 average rating, 32 reviews

Cozy 2BR/1BA Apt | Close to Wesleyan & CT River

Perfect for traveling professionals and visitors, this second-floor unit offers 2 queen bedrooms, a fully equipped kitchen, high-speed Wi-Fi, and a smart TV. What You’ll Love: ✔ Prime Location – 5 mins to Wesleyan & CT River ✔ Comfortable Stay – 2 queen beds & premium linens ✔ Modern Amenities – Fast Wi-Fi, smart TV & stocked kitchen ✔ Free Parking – Hassle-free, on-site spots

4.93 out of 5 average rating, 113 reviews

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.

5 out of 5 average rating, 88 reviews

Home in Middletown

Family Stays, CT

Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our welcoming home is an ideal choice for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you're here to explore Middletown or the surrounding Connecticut towns, you'll have the entire property to yourself for a comfortable and enjoyable stay.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for Middletown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Middletown

Guest suite in Cromwell

4.8 out of 5 average rating, 5 reviews

Private Guest Suite

CatieRating, 5 stars1 week ago

This stay was everything I needed. the property was clean, peaceful and well equipped. The host was very responsive to any needs and made the stay comfortable and inviting. Having access to a fire pit was a lovely touch to unwind on a clear evening.

4.52 out of 5 average rating, 264 reviews

Private Apartment I Near Wesleyan University

JohnRating, 5 stars1 month ago

Everything as advertised. Good wi-fi. Easy access. Good kitchen and bathroom. Thanks

Private room in Middletown

4.98 out of 5 average rating, 139 reviews

Private floor, 3 bedrooms, modern, near Downtown!

TracyRating, 5 stars2 weeks ago

We loved our stay in Marcia's home! She greeted us warmly on arrival, and had everything ready for a wonderful stay. The home was pristinely clean, and even had coffee and treats available. It is close to Wesleyan University - a perfect graduation weekend for our family!

Private room in Frog Hollow

4.88 out of 5 average rating, 266 reviews

Charming & Cozy

AlexisRating, 5 stars3 weeks ago

I only have good things to say about Stephanie's place! Although I was out and about most of the time, the space itself was very quiet and peaceful to come back to at night. There were many written notes and reminders around the house, which is very helpful when you are staying in an unfamiliar place. Check-in/check-out was straight-forward and efficient. You will feel very comfortable here!

4.97 out of 5 average rating, 35 reviews

Your Sweet Spot in Middletown CT

JessicaRating, 5 stars1 month ago

My husband and I enjoyed our stay at the Sweet Spot. It’s a cozy studio in-law apartment built off the main home. The apartment was clean and well kept. We had the pleasure of meeting our host, Bridget, and she shared that they had recently converted the space from a sun room into an apartment. We didn’t have the opportunity to meet Collette. Location is prime as it’s close to downtown Middletown, Wesleyan University, as well as easy access to Route 9. Being close to Main St. made it easy for us to get up in the morning and grab a quick breakfast before heading out for the day. The neighborhood they are in is peaceful, located in a residential area. Would book again.

4.98 out of 5 average rating, 93 reviews

Private room in Hamden

Budget meets Boho-Chic!

DanielRating, 5 stars4 days ago

Fantastic hosts, very welcoming and accommodating. Room was very comfortable and clean. I appreciated the well stocked shower. Guestbook had lots of good local dining and activity recommendations. Would definitely return next time I stay in the New Haven area.

Home in Middletown

4.78 out of 5 average rating, 37 reviews

#29 - Modern 5 Bedroom/2 Bath

JohnRating, 5 stars1 week ago

We were in town for a wedding at the Pavilion on Crystal Lake and this was a perfect location. Thank you for opening your home.