Find Vacation Rentals in Chestertown

Chestertown
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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

Bed & Breakfast Chestertown
e.g. 2/1 - 2/8 (Tue - Tue)
$152 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (662 ratings)
Chestertown, Kent County, Maryland, United States
Details
Official Hotel Website
Details
Bed & Breakfast Chestertown
e.g. 2/1 - 2/8 (Tue - Tue)
$162 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
e.g. 2/18 - 2/25 (Fri - Fri)
$245 per night
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
e.g. 1/28 - 2/4 (Fri - Fri)
$514 per night
Bed & Breakfast ∙ 4 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
e.g. 3/5 - 3/12 (Sat - Sat)
$245 per night
Bed & Breakfast ∙ 4 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
e.g. 2/12 - 2/19 (Sat - Sat)
$245 per night
Bed & Breakfast ∙ 4 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
$219 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
$264 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
Bed & Breakfast Chestertown
$219 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Details
HomeToGo
Details
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Pet-Friendly Homes and Apartments

Motel Pet-friendly Chestertown
$67 per night
Motel ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Pet-friendly
Details
Expedia
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Vacation rentals and apartments with air conditioning

Motel Aircondition Chestertown
$71 per night
Motel ∙ 2 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Aircondition
Details
HomeToGo
Details
Motel Aircondition Chestertown
$83 per night
Motel ∙ 4 guests ∙ 1 bedroom
Chestertown, Kent County, Maryland, United States
Aircondition
Details
HomeToGo
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Frequently Asked Questions

What is the price of vacation rentals in Chestertown?

In Chestertown, vacation rentals start at $70 per night.

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

Tripping.com offers great selection on vacation rentals with 87 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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