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Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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

Guest suite in Chester
Charming Chester Retreat- Near Village Center
*No cleaning fee* This thoughtfully designed 2 bed, 1 bath unit is the perfect blend of style and comfort. The space has been re-designed to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play. Kid friendly! New England getaway / Hidden Gem / Retreat
$195 per night
Cottage in Chester
Brand new cottage "Beriozka" on Cedar Lake
Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.
$184 per night
Loft in Chester
Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.
$136 per night

Stay near Chester's top sights

Photo of Gillette Castle
Gillette Castle7 locals recommend
Photo of Cockaponset State Forest
Cockaponset State Forest9 locals recommend
Photo of Pattaconk 1850 Bar & Grille
Pattaconk 1850 Bar & Grille8 locals recommend
Photo of Red House
Red House6 locals recommend
Photo of Adams Hometown Market
Adams Hometown Market8 locals recommend
Photo of Otto
Otto22 locals recommend

Other great vacation rentals in Chester

Rental unit in Chester
The Millhouse Downtown Chester
$200 per night
Home in Chester
Stunning Artisan Waterfall Escape, Walk Downtown
$239 per night
Private room in Chester
Comfy Artist View at Chester Village
$122 per night
Guesthouse in Chester
Delightful Cottage in Charming Chester
$188 per night
Guest suite in Essex
The Nest
$121 per night
Rental unit in Essex
NEW! Downtown Essex Apartment - Steps to River!
$166 per night
Rental unit in Deep River
Lovely Garden-Level Apartment in Heart of Town
$159 per night
Guest suite in Chester
Colonial Parmelee House at Guest House Retreat
$145 per night
Rental unit in Chester
Chester Village home - amazing location & space!
$228 per night
Rental unit in Deep River
Loft apartment, deck and great water view
$115 per night
Cottage in Deep River
Cottage overlooking the CT river
$105 per night
Home in Essex
Private Suite, firepit and kitchenette
$158 per night
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