Tips
Where to stay

Holiday Rentals in Chestertown, MD

Search and compare Chestertown, MD vacation rentals from hundreds of travel sites and save.

Chestertown, MD, United States
24 May — 25 May2
Chestertown, MD, United States
Fri 24/5
Sat 25/5
...and more

Tips for booking holiday rentals in Chestertown, MD

Gain useful insights and advice for booking the perfect stay in Chestertown, MD. Price data is based on averages over the past 12 months and was last updated on 17 May 2024.
Cheapest month:February
Most expensive month:May
Average price in Chestertown:$430/night
Cheapest price found:$192/night
Cheapest day:Monday
Most expensive day:Saturday
$193 - $738
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$224 - $605
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Other accommodations in Chestertown, MD

Find the perfect holiday rental for your stay in Chestertown, MD. There are 42 hotels in Chestertown, MD and price data was last updated on 17 May 2024. The average price for a hotel in Chestertown, MD is $430/night.
Show all 42 stays
Brampton Bed and Breakfast Inn
Brampton Bed and Breakfast Inn
Brampton Bed and Breakfast Inn
25227 Chestertown Road, Chestertown, MD, United States
2.5 km from city centre
Free Wi-Fi
Air conditioning
$490
Avg. per night
View Deal

Where to stay in Chestertown, MD

Explore different neighbourhoods and areas within Chestertown to find the perfect location for your stay. Map data was last updated on 17 May 2024.
Utilise the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

Facts about staying in Chestertown, MD

Find useful tips and insights about staying in Chestertown to help you make the most of your experience. FAQs were last updated on 17 May 2024.

  • How much does a holiday rental in Chestertown cost?

    $430 per night is how much a holiday rental in Chestertown costs, on average. $193 per night was the cheapest price recently found by our users, though anything for $429 per night or less is a good deal. Keep in mind that Chestertown holiday rental prices fluctuate throughout the year: the most expensive month to book is May, and the cheapest time to book is February.

Find better results for your stay in Chestertown, MD

Millions of Reviews
Real ratings and reviews from millions of guests, just like yourself. Book your perfect stay with confidence!
Best Hotel Deals
HotelsCombined sources over 3 million hotels and properties and compiles them in one place so you can compare the ideal accommodation.
Free cancellation
Plans change — we get it. And that’s why you can search and book hotels and accommodations on HotelsCombined from agencies that offer free cancellation