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Apartment vacation rentals in Middletown

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Top-rated apartment rentals in Middletown

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Rental unit in East Haddam

4.78 out of 5 average rating, 271 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.

Rental unit in Chester

4.93 out of 5 average rating, 343 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

Rental unit in Woodstock Valley

4.93 out of 5 average rating, 377 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

Welcome to the scenic Northeast corner of Ct on beautiful Lake Bungee. Enjoy direct waterfront with stunning sunrises . Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars. BBQ propane grill. Stroll around both lakes . Enjoy bird sightings, nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility !!

Rental unit in Middletown

4.94 out of 5 average rating, 750 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.

Rental unit in Woodmont

4.97 out of 5 average rating, 549 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Rental unit in Chester

4.98 out of 5 average rating, 152 reviews

Charming Chester Retreat-Hidden Gem

This thoughtfully designed 2 bed, 1 bath unit is the perfect blend of style and comfort. The space has been re-designed to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat

Rental unit in Deep River

4.92 out of 5 average rating, 132 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Rental unit in East Haddam

4.9 out of 5 average rating, 149 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.

Rental unit in New Britain

4.93 out of 5 average rating, 136 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. The full kitchen includes stove, fridge, microwave, cookware and a fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Rental unit in Ashford

4.97 out of 5 average rating, 237 reviews

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

Rental unit in Meriden

4.8 out of 5 average rating, 112 reviews

Meriden Metro| Cozy Studio|Pool and Gym

Hello and a warm welcome to Downtown Dream | Meriden Metro | Cozy Retreat Studio! Delighted to have you here! Our amazing location puts you just moments away from various entertainment options, delightful dining experiences, and great shopping opportunities. With easy access to Interstate 91, your travel experience will be smooth and hassle-free. We extend a warm welcome and invite you to book with us!

Rental unit in Middletown

4.93 out of 5 average rating, 100 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.

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Popular amenities for Middletown apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Rental unit in Canaan

4.98 out of 5 average rating, 125 reviews

West Main

Rental unit in New Haven

4.95 out of 5 average rating, 265 reviews

Urban Sanctuary

Rental unit in New London

4.9 out of 5 average rating, 293 reviews

The Whaler’s Loft · Ocean Beach, Mystic & USCGA

Rental unit in Torrington

4.98 out of 5 average rating, 146 reviews

Apartment on Main St.

Rental unit in Branford

4.97 out of 5 average rating, 103 reviews

Ridgeview Suite at Stony Creek Depot

Rental unit in Middletown

4.96 out of 5 average rating, 25 reviews

Your Sweet Spot in Middletown CT

Rental unit in New Haven

4.91 out of 5 average rating, 447 reviews

Edgewood Delight

Rental unit in East Lyme

4.97 out of 5 average rating, 202 reviews

Brand New Direct Lakefront - Panoramic Sunsets

Private apartment rentals

Rental unit in Killingworth

4.93 out of 5 average rating, 29 reviews

Life on the Farm

Rental unit in Waterbury

4.99 out of 5 average rating, 87 reviews

Everything you need! Apartment!

Rental unit in Guilford

4.96 out of 5 average rating, 55 reviews

Cozy Private Lake Q Retreat

Rental unit in Manchester

4.97 out of 5 average rating, 36 reviews

Cozy 1 bedroom clean and quiet

Rental unit in New Britain

5 out of 5 average rating, 14 reviews

Modern 2 Bedroom New Britain Apt

Rental unit in Middletown

5 out of 5 average rating, 11 reviews

Cozy 2-bedroom Middletown

Rental unit in Wallingford

4.8 out of 5 average rating, 35 reviews

Central Town 1BR Furnished Apt - Prime Location

Rental unit in Branford

4.99 out of 5 average rating, 71 reviews

Downtown Branford Retreat - Quiet yet Central Apt

Apartment rentals with a hot tub

Rental unit in Downtown New Haven

4.75 out of 5 average rating, 138 reviews

Luxury Penthouse Minutes to Yale

Rental unit in New Haven

4.56 out of 5 average rating, 9 reviews

Cellar Studio Apartment

Rental unit in Colebrook

5 out of 5 average rating, 25 reviews

Rural retreat in Colebrook CT

Rental unit in Norwich

4.65 out of 5 average rating, 23 reviews

Cozy spa condo with pools near Mystic/Mohegan Sun

Rental unit in Montville

4.81 out of 5 average rating, 101 reviews

Cozy Studio: Indoor Hot Tub & Inground Pool Access

Rental unit in Waterford

5 out of 5 average rating, 22 reviews

Garden Suite: Private, Near Mohegan Sun & USCGA

Rental unit in Norwich

4.92 out of 5 average rating, 12 reviews

Chalet Tré

Rental unit in Norwich

4.88 out of 5 average rating, 8 reviews

Retreat at Norwich Inn and Spa

Quick stats about apartment rentals in Middletown

Total rentals
30 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore