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Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Rental unit

4.78 out of 5 average rating, 276 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Guest favourite

Rental unit

4.94 out of 5 average rating, 760 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.

Cabin

4.89 out of 5 average rating, 641 reviews

Postcard Cabins Machimoodus - NYC/Boston

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favourite

Guest house

4.99 out of 5 average rating, 156 reviews

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.

Guest favourite

Home

5 out of 5 average rating, 106 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

4.96 out of 5 average rating, 136 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

Guest favourite

Home

4.92 out of 5 average rating, 153 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.

Guest favourite

Cottage

4.92 out of 5 average rating, 244 reviews

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.

Guest favourite

Guest suite

5 out of 5 average rating, 548 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.

Guest favourite

Guest house

4.92 out of 5 average rating, 199 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.

Rental unit

4.92 out of 5 average rating, 105 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.

Guest favourite

Rental unit

4.83 out of 5 average rating, 156 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.

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Popular amenities for Middletown holiday rentals

Free parking on premises

Air conditioning

Stay near Middletown's top sights

Powder Ridge Mountain Park & Resort38 locals recommend

Brownstone Exploration & Discovery Park25 locals recommend

Lyman Orchards22 locals recommend

Arrigoni Winery19 locals recommend

Wadsworth Falls State Park17 locals recommend

O'Rourke's Diner12 locals recommend

Other great holiday rentals in Middletown

Guest favourite

Rental unit

4.9 out of 5 average rating, 21 reviews

Hillside Retreat

Guest favourite

Guest suite

4.88 out of 5 average rating, 33 reviews

Spacious Studio in quiet neighborhood.

Guest favourite

Guest suite

5 out of 5 average rating, 32 reviews

Private Bright Studio Retreat with kitchen

Guest favourite

Guest suite

4.94 out of 5 average rating, 98 reviews

Cozy & Private Studio Suite

Guest favourite

Home

4.95 out of 5 average rating, 39 reviews

Hot Tub and pool Home away from home

Guest favourite

Guest house

4.9 out of 5 average rating, 30 reviews

Cozy, Spacious, Central Getaway

Guest favourite

Home

5 out of 5 average rating, 9 reviews

CT River Retreat - Modern Home with CT River Views

Guest favourite

Guest house

5 out of 5 average rating, 17 reviews

Perfect guest house very private

Quick stats about holiday rentals in Middletown

Total rentals
90 properties
Nightly prices starting at
£31 before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Destinations to explore