Naramata Wineries - Vacation Rentals in Chestertown
- Air Conditioner
- Parking
- Internet
- Parking
- Pet Friendly
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Wheelchair Accessible
- Balcony/Terrace
- Air Conditioner
- Parking
- Wheelchair Accessible
Luxury Places to Stay in Chestertown
- Parking
- Pet Friendly
- Pool
Top-Rated Vacation Rentals with a Pool in Chestertown
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pool
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
Pet-Friendly Vacation Rentals in Chestertown
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
Large Vacation Homes & Villas in Chestertown
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
Wheelchair Accessible Vacation Homes in Chestertown
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Wheelchair Accessible
- Air Conditioner
- Wheelchair Accessible
- Child Friendly
- Air Conditioner
- Parking
- Pet Friendly
Chestertown Vacation Rentals and Airbnb Places to Stay Under $200
- Air Conditioner
- Parking
- Security/Safety
- Parking
- Balcony/Terrace
- Security/Safety
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Security/Safety
- Internet
About Chestertown Vacation Rentals
With more than 559 Chestertown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Naramatawineries 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 Naramatawineries 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 1330.83 ft² on average, with prices averaging US $380 a night.
Naramatawineries 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 | 265 |
| Hotels | 177 |
| Holiday Apartments | 91 |
| B&B | 11 |
| Villas | 9 |
| Resorts | 2 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Chestertown
★ Pro Tip: Naramatawineries makes it easy to compare the best listings on Naramatawineries homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Naramatawineries 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
Naramatawineries 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:
- Wades Point Inn on the Bay
- Miller-Dunham House B&B
- Neptune By The Water
- Small House on Gentleman’s Farm
- Pet-Friendly Beach Getaway, Relax by the Bay!
- Apple House- New Townhouse - 2 Car Garage by CCBC & Franklin Sq
- Oasis by the Bay - Waterfront Heated Pool Hot Tub
- Waterfront Home with Private Beach, Stunning Views
- Golden Anchor Retreat Lux Living!
- Beautiful Canton Home w/rooftop deck +Private parking
How many vacation rentals have private pools in Chestertown?
There are 43 vacation rentals with private pools near Chestertown. Top-rated homes that have access to a swimming pool include:
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 559 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.
