Chestertown vacation rentals
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Best Chestertown vacation rentals
Most recommended vacation rentals in Chestertown
Free Wi-Fi
Free Wi-Fi
Pet friendly
Wren Retweet
$201+
$201+
Parking
Free Wi-Fi
Pet friendly
$681+
Free Wi-Fi
Pet friendly
$1,623+
Free Wi-Fi
Pool
Pet friendly
Good to know
Low season | February |
|---|---|
High season | May |
Average price (weeknight) | $205 |
Average price (weekend night) | $443 |
When to book a vacation rental in Chestertown
Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price
Top tips for finding Chestertown vacation rental deals
- The best vacation rental properties in Chestertown are Charming Chestertown Waterfront Cottage (10.0, 25 reviews), Wren Retweet (10.0, 34), and Circa 1900 Home in the Heart of Historic Downtown Chestertown (10.0, 31), based on ratings and reviews from real travelers.
- If you’re looking for a cheap vacation rental in Chestertown, you should consider visiting during the low season. The cheapest vacation homes in Chestertown can be found in February and March.
- The cheapest night for renting a vacation home in Chestertown is Sunday. In contrast, the most expensive is Thursday.
- Book your Chestertown vacation rental more than 90 days before your stay begins to get the best price.
- Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chestertown for 2 days.
- The cheapest Chestertown vacation rental found on KAYAK in the last 2 weeks was $97, while the most expensive was $97.
FAQs when booking a vacation home in Chestertown
What types of vacation rentals are available in Chestertown?
There are loads of different property types that you can make your vacation home in Chestertown. You’ll find apartments, cottages, houses and lodges.
Are there any pet-friendly vacation rentals in Chestertown?
There are a number of dog and pet-friendly Chestertown vacation rentals, with around 26% allowing you to bring your pet along with you.
How can I find vacation rentals near me in Chestertown?
Take a look at our vacation rentals map to find the best vacation rental homes near you.
Where to stay in Chestertown?
Our map will help you find the perfect place to stay in Chestertown by showing you the exact location of each vacation rental.