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Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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

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Apartment in Middletown

4.94 out of 5 average rating, 715 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.

Guest suite in Wethersfield

4.99 out of 5 average rating, 262 reviews

Bright, clean studio in charming Old Wethersfield

Clean, bright studio apartment in the charming village of Old Wethersfield. Stroll to cafes, village green, historic homes and museums. Minutes from I-91 with easy commuting access to downtown Hartford, business and tourist sites, universities, and Hartford Hospital/CCMC. The studio is an in-law suite above our garage. It is attached to our home but has its own keyed entrance. It has a full kitchen, bathroom with shower over tub, closet, queen-sized bed, kitchen table/chairs, and workspace.

Guest suite in Bethlehem

4.99 out of 5 average rating, 213 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Guesthouse in Glastonbury

4.94 out of 5 average rating, 135 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Guest suite in Wallingford

5.0 out of 5 average rating, 509 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. 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. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

Condo in Middletown

4.97 out of 5 average rating, 109 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 kichen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking, swimming pool. 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

Apartment in Glastonbury

4.9 out of 5 average rating, 414 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Apartment in Middletown

4.97 out of 5 average rating, 161 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

Cottage in Middlefield

4.93 out of 5 average rating, 232 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.

Apartment in East Haddam

4.89 out of 5 average rating, 113 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Guesthouse in Glastonbury

4.91 out of 5 average rating, 176 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.

Apartment in Middletown

4.82 out of 5 average rating, 136 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 vacation rentals

Free parking on premises

Air conditioning

Stay near Middletown's top sights

Wadsworth Falls State Park17 locals recommend

Brownstone Exploration & Discovery Park25 locals recommend

Powder Ridge Mountain Park & Resort38 locals recommend

Kidcity Children's Museum9 locals recommend

Arrigoni Winery19 locals recommend

Portland West Golf Course3 locals recommend

Other great vacation rentals in Middletown

Apartment in Windham

4.89 out of 5 average rating, 105 reviews

One bedroom, newly renovated clean and quiet .

Home in Cheshire

5.0 out of 5 average rating, 120 reviews

Pool House

Home in Haddam

5.0 out of 5 average rating, 84 reviews

Cozy Comforts!

Home in Middletown

5.0 out of 5 average rating, 18 reviews

Home with Fiber Optic Internet

Guesthouse in Portland

4.99 out of 5 average rating, 84 reviews

Guesthouse Farm Stay

Apartment in Middletown

4.97 out of 5 average rating, 67 reviews

MIDDLETOWN CT PRIVATE APT - WALK TO WESLEYAN U

Guest suite in Portland

4.93 out of 5 average rating, 15 reviews

Cozy waterview in-law apartment

Farm stay in Glastonbury

5.0 out of 5 average rating, 63 reviews

Historic Farmhouse by the River (Duplex)

Quick stats about vacation rentals in Middletown

Total rentals
80 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
4.7K reviews
Nightly prices starting at
$30 before taxes and fees

Frequently Asked Questions

Do house rentals in Middletown have wifi?
Absolutely! We offer over 40 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Middletown?
Experience the best of Middletown with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 50 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Middletown have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Middletown have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Middletown?
Four-legged friends are welcome in Middletown. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Middletown?
Middletown has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Middletown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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