Find Vacation Rentals in Chester

We have 181 properties to choose from
Chester
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Chester
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Popular Chester Vacation Rentals

Find the perfect Chester vacation rental

House Chester
$464 per night
House ∙ 9 guests ∙ 3 bedrooms
Chester, Kent Island, Maryland, United States
Details
HomeToGo
Details
Details
House Chester
$166 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (68 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$403 per night
House ∙ 6 guests ∙ 3 bedrooms
Chester, Kent Island, Maryland, United States
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Vrbo
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Details
Boat Chester
$170 per night
Boat ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (121 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$179 per night
House ∙ 14 guests ∙ 3 bedrooms
5.0
Outstanding (17 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$407 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (127 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
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Details
House Chester
$485 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$414 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (76 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
Boat Chester
$159 per night
Boat ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (12 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Chester
$1,789 per night
House ∙ 16 guests ∙ 7 bedrooms
4.6
Excellent (10 ratings)
Chester, Kent Island, Maryland, United States
Pool
Details
Vrbo
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Details
House  Chester
$451 per night
House ∙ 5 guests ∙ 2 bedrooms
Chester, Kent Island, Maryland, United States
Pool
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Vrbo
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Details
House  Chester
$1,071 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Chester, Kent Island, Maryland, United States
Pool
Details
Vrbo
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Details
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Pet-Friendly Homes and Apartments

Apartment  Chester
$135 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Chester, Kent Island, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Chester
$133 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
Chester, Kent Island, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chester
$850 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (41 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Details
Vrbo
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Best vacation rentals with a balcony

House  Chester
$666 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding (27 ratings)
Chester, Kent Island, Maryland, United States
Balcony
Details
Vrbo
Details
Details
House  Chester
$128 per night
House ∙ 4 guests ∙ 3 bedrooms
3.9
Good (16 ratings)
Chester, Kent Island, Maryland, United States
Balcony
Details
Vrbo
Details
Details
Villa  Chester
$3,491 per night
Villa ∙ 16 guests ∙ 8 bedrooms
Chester, Kent Island, Maryland, United States
Balcony
Details
Vrbo
Details
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Frequently Asked Questions

What is the average price per night for accommodation in Chester?

Usually, a stay in Chester starts at $128 per night.

Is it possible to find vacation rentals in Chester?

Tripping.com offers great selection on vacation rentals with 181 offers currently available in Chester.

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 Chester

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Chester offers 78 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Chester start at an average price of $334 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, 68 of Chester’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 39 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 67 vacation home rentals. Traveling with your dog or cat? Choose from 22 pet-friendly rentals in Chester 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 7 vacation rental sites in Chester where the top providers in that area are HomeAway, TripAdvisor, and HRS Holidays. There are 40 HomeAway rentals, 12 TripAdvisor short term rentals and 8 HRS Holidays vacation rentals.

Popular Day Trips Near Chester

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