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Vacation rentals in Middlesex County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middlesex County

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

  1. Entire guest suite
  2. East Haddam
Penny Corner Airbnb

Our little town of East Haddam was named one of New York Times "52 places to love in 2021" around the world. My place is located up the hill from Good Speed Opera House on the corner of routes 151 & 82. 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. Please message me for long stay pricing.

$90 per night
SUPERHOST
  1. Entire home
  2. Chester
Unique, fun riverfront cottage

Our cottage is on the Connecticut River in the treasured small town of Chester, half-way between New York and Boston. The house, on our four-acre property, is private and quiet; about two miles from the center of the village which is well-appointed with wonderful restaurants, a professional theater, galleries and one-of-a-kind shops. There are endless hiking and kayaking possibilities . Theater, music and a variety of activities and things to do are all close by.

$140 per night
  1. Entire rental unit
  2. Middletown
Private Apartment II Near Wesleyan University

This private apartment is located in a perfect spot in the central part of Middletown CT. It is in walking distance to downtown Middletown as well as walking distance to Wesleyan University. Main Street Middletown is well-known for its variety of cuisine with scores of reputable restaurants available. Harbor Park on the Connecticut River is approximately one mile away from the apartment.

$68 per night

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Other great vacation rentals in Middlesex County

SUPERHOST
  1. Entire guest suite
  2. Cromwell
Spacious downstairs apartment
$86 per night
SUPERHOST
  1. Private room
  2. Rocky Hill
Penthouse Boho Master Bedroom + Ensuite Bath
$49 per night
SUPERHOST
  1. Private room
  2. Middletown
@WESLEYAN room & ensuite bath
$60 per night
  1. Private room
  2. East Haddam
The Mane House - Ray of Light Farm 2nd floor suite
$98 per night
  1. Private room
  2. Westbrook
Serene Getaway with Private Amenities
$73 per night
SUPERHOST
  1. Entire cottage
  2. Chester
Brand new cottage "Beriozka" on Cedar Lake
$184 per night
  1. Entire rental unit
  2. Haddam
A Little Retreat
$71 per night
SUPERHOST
  1. Entire cottage
  2. East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
$143 per night
  1. Private room
  2. Madison
Madison Cozy Studio with Private Entrance
$90 per night
SUPERHOST
  1. Entire cottage
  2. Portland
Cozy Lake Cottage
$130 per night
SUPERHOST
  1. Entire rental unit
  2. Glastonbury
Quiet 2 bed room apt w/ private entrance.
$75 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
SUNNY PRIVATE 1 BEDROOM APARTMENT
$88 per night