Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Top guest favourite

Guest house in Portland

4.98 out of 5 average rating, 241 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Guest favourite

Flat in Middletown

4.98 out of 5 average rating, 61 reviews

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

Guest favourite

Flat in Middletown

4.94 out of 5 average rating, 834 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.

Superhost

Home in Middletown

4.91 out of 5 average rating, 11 reviews

Large private estate

Secluded home with built-in outdoor grill & firepit. Close to downtown & Wesleyan. The home is spacious with a 1st FL master suite, den, sunken living rm, 8-10pp dining rm, & eat-in kitchen. The front doors open to the enormous foyer & mudrm. Upstairs are 3 bedrooms. The 1st has a queen bed & own bath. The 2nd bedrm has a bunkbed w/double bed, twin bunk, and trundle. The 3rd bedrm has a queen bed. Both share a bath. The pool/spa are not open after 10/15. After 9/1 only the spa will be heated.

Guest favourite

Flat in Middletown

4.83 out of 5 average rating, 60 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.

Superhost

Home in Cromwell

4.83 out of 5 average rating, 107 reviews

Cozy Mid Century home in prime location!

Enjoy an updated, mid century modern inspired, home minutes away from Wesleyan University & TPC River highlands! This eclectic space offers you a cozy retreat that is centrally located. The bedrooms have 1 King, 1 Queen, & 1 Full with luxury mattresses! High speed Wi-Fi, chefs kitchen, dedicated work desk, and garage space! A few mins from RT 9 & 91! Easy to get everywhere in CT!!! Only 5 mins to TPC, 10 mins to Wesleyan, 20 mins to Hartford! Scald protector on shower upstairs!

Guest favourite

Guest suite in Cromwell

4.94 out of 5 average rating, 16 reviews

Private Guest Suite

Private Guest Suite in a New England Cape Cod style home located in a wonderful neighborhood in Cromwell CT. Completely renovated suite. Enjoy private access to a quiet, well lit space with wonderful large illuminating windows and sky light. In-suite washer dryer, double vanity bathroom, bedroom and living room. Internet/TV provided. Bedroom- Full-size bed. Dry kitchen- a toaster oven, microwave, freezer/fridge, Keurig, and water tower. Outdoor pea stone patio, and fire pit.

Top guest favourite

Home in Haddam

5 out of 5 average rating, 135 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!

Guest favourite

Apartment in Middletown

4.93 out of 5 average rating, 166 reviews

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

Top guest favourite

Flat in New Britain

4.96 out of 5 average rating, 211 reviews

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 favourite

Flat in Wallingford

4.96 out of 5 average rating, 386 reviews

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

Guest favourite

Flat in Middletown

4.92 out of 5 average rating, 121 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.