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.

Chestertown Vacation Rentals from $161/night

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Best Chestertown vacation rentals

The Lodge at Great Oak Landing

Chestertown, MD

$161+

Check availability

First Floor Studio Apartment in Historic Chestertown

Chestertown, MD

Free Wi-Fi

$182+

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Carriage House Hideaway In Center of Chestertown

Chestertown, MD

9.9Wonderful(54)

Free Wi-Fi

Pet friendly

$206+

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Newly restored apartment in the heart of Chestertown

Chestertown, MD

Free Wi-Fi

Chestertown, MD

Beautiful, Spacious Waterfront Home, An Easy Walk To Historic Chestertown

Chestertown, MD

$1,023+

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Cottage within walking distance to the Bay!

Chestertown, MD

$329+

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Country Estate in Historic District

Chestertown, MD

Free Wi-Fi

Pet friendly

$368+

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Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown, MD

Free Wi-Fi

$434+

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350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Chestertown, MD

Free Wi-Fi

Pool

Pet friendly

$979+

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Historic Stepne Manor on Maryland's Eastern Shore

Chestertown, MD

Pet friendly

$1,241+

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Historic Manor House on Beautiful Eastern Shore Estate

Chestertown, MD

Free Wi-Fi

Pool

Pet friendly

$1,513+

Check availability

Beautiful home for a family vacation

Chestertown, MD

Free Wi-Fi

Pet friendly

$681+

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Charming Chestertown Waterfront Cottage

Chestertown, MD

$585+

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Historic downtown Chestertown Home. #1 Location.

Chestertown, MD

Free Wi-Fi

$376+

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Carefree Elegance on the Bay, Chestertown MD

Chestertown, MD

$651+

Check availability

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Low season	February
High season	January
Average price (weeknight)	$344
Average price (weekend night)	$318

Cheapest month to stay with an average 54% drop in price.

Most expensive month to stay with an average 119% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

Vacation rentals in Chestertown are around 59% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chestertown.
The best vacation rental properties in Chestertown are Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities (10.0, 26 reviews), Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town (10.0, 21), and Country Estate in Historic District (10.0, 41), 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 November.
The cheapest night for renting a vacation home in Chestertown is Tuesday. In contrast, the most expensive is Monday.
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.

See more tips

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.