Find Vacation Rentals in Chestertown

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Chestertown
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Chestertown
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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
from $421 per night
House ∙ 8 guests ∙ 3 bedrooms
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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House Chestertown
from $408 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (16 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $569 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (108 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $165 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (3 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $638 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (34 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $197 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (98 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $284 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (93 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $472 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (99 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Details
House Chestertown
from $828 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (34 ratings)
Chestertown, Kent County, Maryland, United States
Details
Vrbo
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Vacation rentals and apartments with air conditioning

House  Chestertown
from $1,084 per night
House ∙ 14 guests ∙ 6 bedrooms
4.9
Outstanding (29 ratings)
Chestertown, Kent County, Maryland, United States
Air conditioning
Details
Vrbo
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Details
Apartment  Chestertown
from $199 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (27 ratings)
Chestertown, Kent County, Maryland, United States
Air conditioning
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Vrbo
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Details
House  Chestertown
from $261 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (57 ratings)
Chestertown, Kent County, Maryland, United States
Air conditioning
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Vrbo
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Vacation rentals with Wi-Fi

House  Chestertown
from $518 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding (50 ratings)
Chestertown, Kent County, Maryland, United States
Internet
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Vrbo
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Details
House  Chestertown
from $415 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (83 ratings)
Chestertown, Kent County, Maryland, United States
Internet
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Vrbo
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Bed and breakfast  Chestertown
from $281 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Internet
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Agoda
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Vacation homes and rentals with a yard

House  Chestertown
from $795 per night
House ∙ 15 guests ∙ 5 bedrooms
5.0
Outstanding (48 ratings)
Chestertown, Kent County, Maryland, United States
Yard
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Vrbo
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House  Chestertown
from $772 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (33 ratings)
Chestertown, Kent County, Maryland, United States
Yard
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Vrbo
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Details
House  Chestertown
from $2,435 per night
House ∙ 30 guests ∙ 11 bedrooms
5.0
Outstanding (16 ratings)
Chestertown, Kent County, Maryland, United States
Yard
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Vrbo
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Frequently Asked Questions

What is the price of vacation rentals in Chestertown?

In Chestertown, vacation rentals start at $72 per night.

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

Tripping.com offers great selection on vacation rentals with 71 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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