Find Vacation Rentals in Chestertown

We have 68 properties to choose from
Chestertown
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Chestertown
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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
$452 per night
House ∙ 14 guests ∙ 5 bedrooms
4.9
Outstanding (43 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$826 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (26 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$452 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (102 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$454 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (96 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$411 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (12 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$293 per night
House ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding (92 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$222 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (96 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
Apartment Chestertown
$150 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (93 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
Details
Details
House Chestertown
$239 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (57 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
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Recommended Rentals With Pools

House  Chestertown
$494 per night
House ∙ 14 guests ∙ 5 bedrooms
Chestertown, Kent County, Maryland, United States
Pool
Details
HomeToGo
Details
Details
Apartment  Chestertown
$131 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.8
Outstanding (101 ratings)
Chestertown, Kent County, Maryland, United States
Pool
Details
Vrbo
Details
Details
House  Chestertown
$2,376 per night
House ∙ 30 guests ∙ 11 bedrooms
5.0
Outstanding (16 ratings)
Chestertown, Kent County, Maryland, United States
Pool
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

House  Chestertown
$666 per night
House ∙ 15 guests ∙ 5 bedrooms
5.0
Outstanding (48 ratings)
Chestertown, Kent County, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chestertown
$227 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (98 ratings)
Chestertown, Kent County, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chestertown
$759 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (32 ratings)
Chestertown, Kent County, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
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Best vacation rentals with a balcony

House  Chestertown
$443 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding (48 ratings)
Chestertown, Kent County, Maryland, United States
Balcony
Details
Vrbo
Details
Details
House  Chestertown
$612 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (9 ratings)
Chestertown, Kent County, Maryland, United States
Balcony
Details
Vrbo
Details
Details
House  Chestertown
$1,058 per night
House ∙ 14 guests ∙ 6 bedrooms
4.9
Outstanding (29 ratings)
Chestertown, Kent County, Maryland, United States
Balcony
Details
Vrbo
Details
Details
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Frequently Asked Questions

What is the price of vacation rentals in Chestertown?

In Chestertown, vacation rentals start at $83 per night.

Can I see all vacation rentals that are available in Chestertown?

Tripping.com offers great selection on vacation rentals with 68 offers currently available in Chestertown.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Chestertown

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Chestertown offers 54 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Chestertown start at an average price of $326 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 45 of Chestertown’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 8 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 39 vacation home rentals. Traveling with your dog or cat? Choose from 18 pet-friendly rentals in Chestertown that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 6 vacation rental sites in Chestertown where the top providers in that area are HomeAway, TripAdvisor, and HRS Holidays. There are 28 HomeAway rentals, 10 TripAdvisor short term rentals and 6 HRS Holidays vacation rentals.

Popular Day Trips Near Chestertown

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