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.

Guest favourite
Flat in Middletown
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.
11–18 Sep
$141 SGD per night
4.94 out of 5 average rating, 695 reviews
Guest favourite
Guest suite in Wethersfield
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.
22–29 Apr
$139 SGD per night
4.99 out of 5 average rating, 246 reviews
Guest favourite
Guest house in Glastonbury
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.
25 Apr – 2 May
$173 SGD per night
4.96 out of 5 average rating, 133 reviews

Popular amenities for Middletown holiday rentals

Stay near Middletown's top sights

Wadsworth Falls State Park17 locals recommend
The Wadsworth Mansion at Long Hill4 locals recommend
Kidcity Children's Museum9 locals recommend
Mondo4 locals recommend
Brownstone Exploration & Discovery Park25 locals recommend
Eli Cannon's6 locals recommend

Other great holiday rentals in Middletown

Guest favourite
Home in Haddam
Cozy Comforts!
12–19 Nov
$123 SGD per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Guest house in Portland
Guesthouse Farm Stay
9–16 Oct
$175 SGD per night
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Middletown
MIDDLETOWN CT PRIVATE APT - WALK TO WESLEYAN U
25 Dec – 1 Jan
$200 SGD per night
4.97 out of 5 average rating, 60 reviews
Guest favourite
Home in Middletown
Home away from home
27 Jun – 4 Jul
$239 SGD per night
4.97 out of 5 average rating, 35 reviews
Guest favourite
Farm stay in Glastonbury
Rustic Farmhouse by the River (Duplex)
20–27 Mar
$145 SGD per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Middletown
Hot Tub and pool Home away from home
20–27 Aug
$566 SGD per night
4.93 out of 5 average rating, 15 reviews
Guest favourite
Cottage in Middlefield
Anchors' Away-
27 Feb – 6 Mar
$335 SGD per night
5.0 out of 5 average rating, 82 reviews
Guest favourite
Flat in New Britain
Spacious Cozy Guest Suite
16–23 Nov
$113 SGD per night
4.96 out of 5 average rating, 79 reviews
Guest favourite
Loft in Durham
The Durham - Circa 1900s Dairy Farm
9–16 Apr
$150 SGD per night
4.88 out of 5 average rating, 42 reviews
Guest favourite
Home in East Haddam
Romantic Getaway at The Lake!
23–30 Aug
$268 SGD per night
4.95 out of 5 average rating, 84 reviews
Guest favourite
Guest house in Wallingford
The Garden Loft - A Charming Choate Stay
5–12 Sep
$272 SGD per night
5.0 out of 5 average rating, 65 reviews
Guest favourite
Home in East Hampton
Waterfront Lake House
19–26 Apr
$597 SGD per night
4.94 out of 5 average rating, 17 reviews

Quick stats about holiday rentals in Middletown

Total rentals

80 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

4.8K reviews

Nightly prices starting at

$54 SGD before taxes and fees

Destinations to explore