The Beaches Estates - Vacation Rentals in Chestertown
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Wheelchair Accessible
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
Luxury Places to Stay in Chestertown
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
Top-Rated Vacation Rentals with a Pool in Chestertown
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
Pet-Friendly Vacation Rentals in Chestertown
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Large Vacation Homes & Villas in Chestertown
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Bedding/Linens
- Child Friendly
Chestertown Varoom and Airbnb Places to Stay Under $200
- Air Conditioner
- TV
- Balcony/Terrace
- Air Conditioner
- TV
- Balcony/Terrace
Instantly Bookable Vacation Homes in Chestertown
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
About Chestertown Vacation Rentals
With more than 65 Chestertown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thebeachestates and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chestertown.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thebeachestates Chestertown, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chestertown. Places to stay near Chestertown are 875.3 ft² on average, with prices averaging $498 a night.
Thebeachestates makes it easy and safe to find and compare vacation rentals in Chestertown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chestertown
| Type | Count |
|---|---|
| Vacation Homes | 44 |
| Holiday Apartments | 8 |
| Hotels with Suites | 5 |
| Cottages | 3 |
| Cabin Rentals | 2 |
| Others | 2 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Chestertown
★ Pro Tip: Thebeachestates makes it easy to compare the best listings on Thebeachestates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thebeachestates homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chestertown.
Weather in Chestertown
View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.
Top Attractions Around Chestertown, MD
Thebeachestates offers a large selection of top attractions around Chestertown. Research things to do on your vacation before you visit Chestertown.
Other Places to Stay Near Chestertown, MD
Chestertown Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chestertown?
There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chestertown:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Country Estate in Historic District
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
- Historic Manor House on Beautiful Eastern Shore Estate
- Harbor View Haven | Waterfront w/Hot Tub + Dock!
Which vacation homes in Chestertown are best for families?
If you are looking for a family-friendly vacation home in Chestertown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestertown:
How many vacation rentals are available in Chestertown?
Currently, the total number of properties listed in 2026 is over 65 in the Chestertown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chestertown.
