Find Vacation Rentals in Chestertown

We have 72 properties to choose from
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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
from $685 per night
House ∙ 14 guests ∙ 4 bedrooms

300 m² House

5.0
Outstanding(1 rating)
Chestertown, Kent County, Maryland, United States
Details
House Chestertown
from $762 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(47 ratings)
Chestertown, Kent County, Maryland, United States
Details
Apartment Chestertown
from $259 per night
4 guests ∙ 2 bedrooms

Apartment

4.9
Outstanding(33 ratings)
Chestertown, Kent County, Maryland, United States
Details
Apartment Chestertown
from $142 per night
Apartment ∙ 2 guests ∙ 1 bedroom

48 m² Apartment

5.0
Outstanding(40 ratings)
Chestertown, Kent County, Maryland, United States
Details
House Chestertown
from $501 per night
10 guests ∙ 3 bedrooms

House

5.0
Outstanding(99 ratings)
Chestertown, Kent County, Maryland, United States
Details
House Chestertown
from $338 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(93 ratings)
Chestertown, Kent County, Maryland, United States
Details
House Chestertown
from $218 per night
House ∙ 6 guests ∙ 3 bedrooms

134 m² House

5.0
Outstanding(13 ratings)
Chestertown, Kent County, Maryland, United States
Details
House Chestertown
from $295 per night
6 guests ∙ 4 bedrooms

House

5.0
Outstanding(84 ratings)
Chestertown, Kent County, Maryland, United States
Details
House Chestertown
from $639 per night
8 guests ∙ 4 bedrooms

House

4.9
Outstanding(34 ratings)
Chestertown, Kent County, Maryland, United States
Details
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Vacation rentals and apartments with air conditioning

Apartment  Chestertown
from $161 per night
4 guests ∙ 3 bedrooms

Apartment

Chestertown, Kent County, Maryland, United States
Air conditioning
Details
House  Chestertown
from $753 per night
House ∙ 14 guests ∙ 4 bedrooms

300 m² House

4.9
Outstanding(12 ratings)
Chestertown, Kent County, Maryland, United States
Air conditioning
Details
House  Chestertown
from $322 per night
6 guests ∙ 3 bedrooms

House

Chestertown, Kent County, Maryland, United States
Air conditioning
Details
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Vacation rentals with Wi-Fi

Motel  Chestertown
from $70 per night
Motel ∙ 2 guests ∙ 1 bedroom

42 m² Motel

Chestertown, Kent County, Maryland, United States
Internet
Details
Motel  Chestertown
from $75 per night
Motel ∙ 4 guests ∙ 1 bedroom

46 m² Motel

Chestertown, Kent County, Maryland, United States
Internet
Details
Motel  Chestertown
from $69 per night
Motel ∙ 4 guests ∙ 1 bedroom

Driftwood Inn

3.1
Chestertown, Kent County, Maryland, United States
Internet
Details
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Vacation rentals with a balcony

House  Chestertown
from $470 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(26 ratings)
Chestertown, Kent County, Maryland, United States
Balcony
Details
House  Chestertown
from $1,141 per night
14 guests ∙ 6 bedrooms

House

4.9
Outstanding(32 ratings)
Chestertown, Kent County, Maryland, United States
Balcony
Details
House  Chestertown
from $582 per night
10 guests ∙ 3 bedrooms

House

5.0
Outstanding(14 ratings)
Chestertown, Kent County, Maryland, United States
Balcony
Details
Show more

Frequently Asked Questions

What is the price of vacation rentals in Chestertown?

In Chestertown, vacation rentals start at $69 per night.

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

Tripping.com offers great selection on vacation rentals with 72 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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