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
Guest suite in New Britain
Clean, Quiet and Safe w/Amenities to spare!
This newly renovated in-law apartment (basement) has a private entrance and Ring security protection in the quaint, quiet neighborhood bordering Berlin/New Britain. Come relax, enjoy biking trails, local restaurants and public parks. Renovated with attention to detail, this place has all the comforts of home. Includes two flat screen TVs in bedroom and living room with Fire sticks (cable/movies), two fireplaces and granite vanity & breakfast bar. Working professionals get 10% off long term stays
16–23 Jun
$106 SGD per night
4.92 out of 5 average rating, 129 reviews
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.
20–27 Oct
$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.
8–15 Nov
$142 SGD per night
4.99 out of 5 average rating, 246 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 Cheshire
Pool House
15–22 Jan
$169 SGD per night
5.0 out of 5 average rating, 116 reviews
Guest favourite
Apartment in Middletown
Entire place to yourself Cromwell/Middletown Line
3–10 Feb
$140 SGD per night
4.97 out of 5 average rating, 98 reviews
Guest favourite
Home in Haddam
Cozy Comforts!
14–21 Sep
$126 SGD per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Guest house in Portland
Guesthouse Farm Stay
24–31 Aug
$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
17–24 Nov
$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
Historic Farmhouse by the River (Duplex)
1–8 Feb
$149 SGD per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Guest suite in Portland
Cozy waterview in-law apartment
10–17 Jun
$148 SGD per night
4.91 out of 5 average rating, 11 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
Flat in New Britain
Spacious Cozy Guest Suite
20–27 Nov
$113 SGD per night
4.96 out of 5 average rating, 79 reviews
Guest favourite
Cottage in Middlefield
Anchors' Away-
27 Jul – 3 Aug
$335 SGD per night
5.0 out of 5 average rating, 82 reviews
Guest favourite
Flat in Clinton
Cozy Shoreline Getaway
10–17 May
$133 SGD per night
4.98 out of 5 average rating, 48 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