Vacation 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, 802 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, 140 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

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, 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!

4.93 out of 5 average rating, 153 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

4.92 out of 5 average rating, 247 reviews

Cottage in Middlefield

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

4.95 out of 5 average rating, 191 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.

Guesthouse in Glastonbury

4.92 out of 5 average rating, 204 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

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.

Vacation rentals for every style

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Popular amenities for Middletown vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Middletown

Guest suite in Cromwell

4.75 out of 5 average rating, 4 reviews

Private Guest Suite

ItchungRating, 5 stars2 weeks ago

Great location! Brand new! Impeccably clean. Beautiful surroundings with lots of birds and bunnies. Quiet, easy drive to Middletown. Would definitely stay here again. Thank you.

Superhost

Cottage in Portland

4.61 out of 5 average rating, 18 reviews

Lake Cottage Getaway

NanaRating, 5 stars7 months ago

Had a really wonderful time here for my friends’ trip. Kimberly was a communicative and amazing host, and the cottage was clean and well-stocked. The location is also perfect if you are hoping to enjoy some peace and relaxation, with nearby parks and trails available for exploration.

4.92 out of 5 average rating, 26 reviews

Apartment in Meriden

Hillside Retreat

OliviaRating, 5 stars1 month ago

this place is absolutely beautiful and i will 100% be staying here again, the location is amazing and there’s food places and stuff to do so close by, we loved staying here it’s beautiful ♥️

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

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.

4.95 out of 5 average rating, 41 reviews

Home in Middletown

Hot Tub and pool Home away from home

KristenRating, 5 stars5 months ago

Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!

Guesthouse in East Hampton

4.84 out of 5 average rating, 56 reviews

Your Own Barn Loft Suite Among the Treetops

ChristineRating, 5 stars2 months ago

This is a fabulous place to stay! Beautifully decorated and all the comforts of home. Andrew and Jessica were gracious hosts and great communicators. We will definitely stay again!