60+ Private Villas and Holiday Rentals in Chester |
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  2. Connecticut
  3. Old Saybrook
  4. Chester

Chester Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chester

Discover more than 60 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 1114.58 ft², with nightly prices averaging US $466.

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.

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Top Accommodation Types in Chester

Type Count
Vacation Homes 26
Holiday Apartments 16
Cottages 10

Use these Quick Filters to Find a Holiday Rental in Chester

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chester.

Weather in Chester, CT

View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chester, CT

Casai offers a large selection of top attractions around Chester . Research things to do on your vacation before you visit Chester.


Norma Terris Theater
Chester Creek Marina
Mohegan Sun Casino
Mohegan Sun Arena
Ocean Beach Park
Toyota Presents Oakdale Theatre
Quinnipiac University
Wesleyan University
Essex Steam Train
Connecticut College
Hammonasset Beach State Park
Naval Submarine Base New London
Choate Rosemary Hall
United States Coast Guard Academy
Essex Library
New London Ferry Dock
Clinton Crossing Premium Outlets
US Coast Guard Academy
Branford Hills Plaza Shopping Center

Other Places to Stay in Chester, CT


Chester Creek Marina 54 Properties
Chester Center 49 Properties
Norma Terris Theater 49 Properties

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:

Which holiday homes in Chester are best for families?

If you're searching for a family-friendly holiday home in Chester, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chester:

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

As of 2025, Casai boasts over 60 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 (2) 
Neighborhood Property Count
Deep River Center Vacation Rentals in Old Saybrook, Connecticut 25
Chester Center Vacation Rentals in Old Saybrook, Connecticut 49

People Also Ask

There are 60 Chester, CT Holiday Rentals

Recently Booked Holiday Rentals in Chester