Find Vacation Rentals in Chester

We have 179 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
$155 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (66 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$424 per night
House ∙ 6 guests ∙ 3 bedrooms
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
Apartment Chester
$139 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
Boat Chester
$176 per night
Boat ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (120 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$168 per night
House ∙ 14 guests ∙ 3 bedrooms
5.0
Outstanding (16 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$377 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (128 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$405 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (76 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
House Chester
$762 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (41 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
Details
Details
Boat Chester
$182 per night
Boat ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (11 ratings)
Chester, Kent Island, Maryland, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Chester
$453 per night
House ∙ 5 guests ∙ 2 bedrooms
Chester, Kent Island, Maryland, United States
Pool
Details
Vrbo
Details
Details
House  Chester
$1,782 per night
House ∙ 16 guests ∙ 7 bedrooms
4.6
Excellent (10 ratings)
Chester, Kent Island, Maryland, United States
Pool
Details
Vrbo
Details
Details
House  Chester
$1,066 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
$136 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Chester, Kent Island, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chester
$474 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding (24 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
Mobile home  Chester
$208 per night
Mobile home ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Details
Vrbo
Details
Details
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Vacation Homes With Terraces

House  Chester
$408 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (11 ratings)
Chester, Kent Island, Maryland, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Chester
$333 per night
House ∙ 6 guests ∙ 2 bedrooms
4.6
Excellent (10 ratings)
Chester, Kent Island, Maryland, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Chester
$202 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (21 ratings)
Chester, Kent Island, Maryland, United States
Balcony/Patio
Details
Vrbo
Details
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 $135 per night.

Is it possible to find vacation rentals in Chester?

Tripping.com offers great selection on vacation rentals with 179 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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