Vacation rentals in Chester

Find and book unique accommodations on Airbnb

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Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Gillette Castle State Park83 locals recommend
Cockaponset State Forest9 locals recommend
Gillette Castle7 locals recommend
Red House6 locals recommend
Adams Hometown Market8 locals recommend
Pattaconk 1850 Bar & Grille8 locals recommend

Other great vacation rentals in Chester

Guest favorite
Apartment in Middletown
Apartment Near Wesleyan, Downtown, Wedding Venues!
Jul 3 – 10
$112 per night
4.99 out of 5 average rating, 140 reviews
Guest favorite
Home in Haddam
Charming 1806 farm house close to the CT River.
Aug 7 – 14
$335 per night
4.93 out of 5 average rating, 120 reviews
Guest favorite
Cottage in Middlefield
Lake Beseck cottage
Sep 12 – 19
$106 per night
4.93 out of 5 average rating, 228 reviews
Guest favorite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
Dec 26 – Jan 2
$156 per night
4.99 out of 5 average rating, 82 reviews
Guest favorite
Apartment in Chester
Gingerbread Apartment, Walk Downtown
Jun 4 – 11
$138 per night
4.92 out of 5 average rating, 39 reviews
Guest favorite
Guesthouse in Chester
Delightful Cottage in Charming Chester
Nov 28 – Dec 5
$188 per night
5.0 out of 5 average rating, 41 reviews
Guest favorite
Apartment in Clinton
Cozy Shoreline Getaway
May 10 – 17
$89 per night
4.98 out of 5 average rating, 48 reviews
Guest favorite
Apartment in Chester
The Millhouse Downtown Chester
Feb 1 – 8
$211 per night
4.99 out of 5 average rating, 68 reviews

Quick stats about vacation rentals in Chester

Total rentals

10 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

2K reviews

Nightly prices starting at

$100 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Middlesex County
  5. Chester