Holiday houses in Middletown

5 out of 5 average rating, 45 reviews

Renovated 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, 805 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

4.81 out of 5 average rating, 52 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

Guesthouse 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, 126 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

Condo 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, 193 reviews

Apartment 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.

Superhost

4.86 out of 5 average rating, 113 reviews

Perfect Private "Downtown Village" Apartment

Private Second 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.

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

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

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Houses

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

Popular amenities for Middletown holiday rentals

Kitchen

Wi-Fi

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!

Home in Middletown

4.67 out of 5 average rating, 30 reviews

#40 - Spacious, Sleek & Cozy

CatherineRating, 5 stars2 weeks ago

This house was spotless, well appointed with extra blankets and everything you could possibly need in a kitchen, and in a quiet and safe area. We were there with our adult sons and my elderly mother, and we were all very comfortable with the spacious layout, 2 full bathrooms, dining and living spaces, a nice outdoor deck, and ate meals there as well as in Middletown. Conveniently located to Wesleyan, grocery stores, etc. Would highly recommend to families and groups.

4.98 out of 5 average rating, 93 reviews

Private room in Hamden

Budget meets Boho-Chic!

DanielRating, 5 stars1 week 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.

4.83 out of 5 average rating, 76 reviews

Private room in Berlin

Red Door Retreat West

TashaRating, 5 stars5 months ago

Thank you so much Stacey for allowing me to stay at your property. I had a last minute work gig and I was able to instantly book my stay. The space was very comfortable and quiet. I will be booking again when I am back in the area. Thank you again for great communication!

4.52 out of 5 average rating, 25 reviews

Private Apt in Middletown-Wesleyan

NaluRating, 5 stars1 month ago

We had a great time staying here while visiting Wesleyan. A great location close to campus.