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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.

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.
8–15 Dec, Individual Host
£112 per night
Guest favourite
Guest suite in Wallingford
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.
28 Dec – 4 Jan, Individual Host
£75 per night
Guest favourite
Flat in Middletown
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!
8–15 May
£126 per night

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
Mondo4 locals recommend
Brownstone Exploration & Discovery Park25 locals recommend
Eli Cannon's6 locals recommend
Kidcity Children's Museum9 locals recommend

Other great holiday rentals in Middletown

Guest favourite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
1–8 Feb, Professional Host
£206 per night
Guest favourite
Guest house in Glastonbury
Unique luxurious private building in historic area
24 Apr – 1 May, Individual Host
£154 per night
Guest favourite
Guest house in Glastonbury
Charming Barn Apartment
4–11 Mar, Individual Host
£136 per night
Superhost
Cabin in East Haddam
Getaway Machimoodus - NYC/Boston
23–30 Nov, Professional Host
£283 per night
Guest favourite
Guest suite in Wethersfield
Bright, clean studio in charming Old Wethersfield
25 Mar – 1 Apr, Individual Host
£108 per night
Guest favourite
Guest house in Granby
Windy Top Cottage ~ A Romantic "European" Getaway
12–19 Jan, Individual Host
£152 per night
Guest favourite
Guest suite in Waterbury
Private 1 bedroom apartment in central Connecticut
23–30 Jan, Individual Host
£84 per night
Guest favourite
Apartment in Middletown
Entire place to yourself Cromwell/Middletown Line
3–10 Feb
£115 per night
Guest favourite
Guest house in Portland
Guesthouse Farm Stay
13–20 Jul
£138 per night
Guest favourite
Home in Haddam
Cozy Comforts!
13–20 Jul
£135 per night
Guest favourite
Flat in Middletown
MIDDLETOWN CT PRIVATE APT - WALK TO WESLEYAN U
25 Sept – 2 Oct, Individual Host
£166 per night
Guest favourite
Home in Middletown
Home away from home
11–18 Jul
£188 per night

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

£32 before taxes and fees

Destinations to explore