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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
River Tavern16 locals recommend
Otto15 locals recommend
Grano Arso16 locals recommend
Lavender Pond Farm8 locals recommend
Simon's Marketplace9 locals recommend

Other great vacation rentals in Chester

Superhost
Home in Litchfield County
4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

JadeRating, 5 stars2 months ago
We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!
Superhost
Home in Waterford
4.94 out of 5 average rating, 18 reviews

Summer Beach Cottage Harknes, Ocean Beach N

JenniferRating, 5 stars8 months ago
It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.
Superhost
Home in Cornwall
4.82 out of 5 average rating, 97 reviews

State Forest Getaway

SahilyRating, 5 stars1 week ago
This Airbnb was a great place to stay at. Although my family didn’t stay long, we just wanted to get out of the routine and find a place to relax for a bit and forget about day to day responsibilities. This place was clean and the host was very friendly; I would 10/10 recommend this place to others!
Guest favourite
Cabin in Rocky Point
4.89 out of 5 average rating, 486 reviews

Great little place just for a couple

MeganRating, 5 stars2 days ago
A wonderful spot and wonderful host. Everything was cheery and thoughtfully done. I knocked off a star for the price mostly because I wasn't anticipating how expensive it is to get around by Uber in the area, and to find an accessible grocery store - otherwise necessary to have a car. Ended up ordering UberEats... my mom was at another Airbnb down the road and the difference in how we were treated as guests was astronomical. Marina did not charge me for having my little dog, there was a little firewood for us to use, fresh coffee and tea, and all the amenities! Marina was also very responsive and kind, and left a very helpful note about whether the beach is public or not. 100% recommend. In contrast, my mom felt badly treated by the host, the place was poorly kept and she felt it was way overpriced in comparison to mine (Marina's). Good thing she was able to come here during the day, and we spent most of our time here, in the yard or the short walk to the beach.
Guest favourite
Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 50 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

ChrisRating, 5 stars1 day ago
My family and I enjoyed our stay. The accommodation was well appointed with all ameneties and cooking utilities to provide for a wonderful stay. We enjoyed the private back yard area and porch for dinners outside. Harvey's Beach is a walkable and we enjoyed some beach time there. Irina is a very responsive host and provided some great local tips on restaruants and places to visit. We would recommend this spot for folks looking for a location both close to beaches and town area. The accommodation is welcoming and very suitable for families or groups.
Guest favourite
Home in Mystic
4.89 out of 5 average rating, 9 reviews

Family Friendly Mystic Retreat - Close To Town

AlyssaRating, 5 stars1 week ago
Cory was a great host! So responsive and accommodating! The space was beautiful and we had an amazing time for our quick visit to Mystic!

Quick stats about vacation rentals in Chester

  • Total rentals

    20 properties

  • Nightly prices starting at

    $69 CAD before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

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