Chester Holiday Rentals

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Compare Villas, Resorts, & Rentals in Chester

102 villas and rentals
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Luxury Holiday Rentals in Chester

Over 93+ Luxury Holiday Rentals in or Near Chester
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Top-Rated Holiday Rentals with a Pool in Chester

Over 5+ The Best Private Villas and Holiday Rentals in Chester with a Pool
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Pet-Friendly Holiday Rentals in Chester

Over 29+ Pet-Friendly Holiday Rentals in or Near Chester
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Large Holiday Rentals and Private Villas in Chester

Over 11+ Large Holiday Rentals and Private Villas in or Near Chester
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Wheelchair Accessible Holiday Homes in Chester

Over 1+ Wheelchair Accessible Holiday Homes in or Near Chester

Chester Private Villas and Holiday Homes Under $200

Over 9+ Chester Private Villas and Holiday Homes Under $200
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Instantly Bookable Holiday Homes in Chester

Over 28+ Instantly Bookable Holiday Homes in or Near Chester
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Book a Last Minute Place to Stay in Chester

About Casai's Private Villas and Holiday Rentals in Chester

Discover more than 102 vacation rentals available in Chester. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chester.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chester, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chester. On average, places to stay near Chester offer 1057.85 ft², with nightly prices averaging US $390.

With Casai, finding and comparing holiday rentals in Chester is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other places to stay near the Chester, VT


DaVallia Art & Accents 60 Properties
Bonnie's Bundles Dolls 60 Properties
Chester Depot 52 Properties

There are 102 Chester, VT Holiday Rentals

Recently Booked Holiday Rentals in Chester

Frequently Asked Questions About Chester?

What are the top holiday rentals in Chester?

With numerous options available in Chester, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chester:

How many Casai.com holiday rentals are available in Chester?

As of 2026, Casai boasts over 102 properties listed in the Chester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chester.

Nearby Neighborhood (1)

NeighborhoodProperty Count
Chester Depot Vacation Rentals in Chester, Vermont 52