Chester Holiday Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- 3370 ft² House
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Barbecue/Outdoor Cooking
- Child Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
Luxury Holiday Rentals in Chester
- Air Conditioner
- Pet Friendly
- Balcony/Terrace
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
Top-Rated Holiday Rentals with a Pool in Chester
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- 301 ft² Hotel
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
Pet-Friendly Holiday Rentals in Chester
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- View
Large Holiday Rentals and Private Villas in Chester
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
- Pool
- Private Pool
- Bedding/Linens
Wheelchair Accessible Holiday Homes in Chester
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Chester Private Villas and Holiday Homes Under $200
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Fireplace/Heating
Instantly Bookable Holiday Homes in Chester
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
Book a Last Minute Place to Stay in Chester
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.
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
- Pool
- |
- Pet Friendly
- |
- Eco-friendly
- |
★ 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.
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.
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:
- Island Life! Kent Island Waterfront with Pool-Bring your boat!
- Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Cass-Away Luxury Houseboat
- Cass-N-Reel Luxury Houseboat
- Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing
- Waterfront Sunset Bayview: sleeps 6
- Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
- Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
- Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
- DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 8-10-PETS ALLOWED.
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.