48+ Private Villas and Holiday Rentals in Chester |
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  3. Chester

Chester Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chester

Discover more than 48 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 1115.68 ft², with nightly prices averaging US $533.

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
Cottages 3
Holiday Apartments 2
Villas 1

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, MD

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, MD

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


Chesapeake Exploration Center
U.S. Naval Academy
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
St. Michaels Winery
Queenstown Premium Outlets
Annapolis Maritime Museum
Chesapeake Bay Maritime Museum
Oxford Museum
Queenstown Harbor Golf Club
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club

Other Places to Stay in Chester, MD


Chesapeake Exploration Center 46 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 48 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.


People Also Ask

There are 48 Chester, MD Holiday Rentals

Recently Booked Holiday Rentals in Chester