Find Vacation Rentals in Chester

We have 183 properties to choose from
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Popular Chester Vacation Rentals

Find the perfect Chester vacation rental

House Chester
from $413 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(133 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
Houseboat Chester
from $177 per night
Houseboat ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(128 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $157 per night
House ∙ 4 guests ∙ 3 bedrooms
3.9
Good(16 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $176 per night
House ∙ 14 guests ∙ 3 bedrooms
5.0
Outstanding(32 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $416 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(11 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $605 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding(7 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
Houseboat Chester
from $157 per night
Houseboat ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(28 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $595 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding(37 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $477 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding(16 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Chester
from $1,069 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(3 ratings)
Chester, Kent Island, Maryland, United States
Pool
Vrbo
Details
House  Chester
from $1,789 per night
House ∙ 16 guests ∙ 7 bedrooms
4.4
Very good(16 ratings)
Chester, Kent Island, Maryland, United States
Pool
Vrbo
Details
House  Chester
from $442 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(49 ratings)
Chester, Kent Island, Maryland, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Chester
from $614 per night
House ∙ 9 guests ∙ 3 bedrooms
Chester, Kent Island, Maryland, United States
Pet-friendly
HomeToGo
Details
House  Chester
from $330 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(10 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Vrbo
Details
Condo  Chester
from $290 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.6
Excellent(13 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Vrbo
Details
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Vacation Homes With Terraces

House  Chester
from $466 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(16 ratings)
Chester, Kent Island, Maryland, United States
Balcony/Patio
Vrbo
Details
House  Chester
from $507 per night
House ∙ 8 guests ∙ 2 bedrooms
Chester, Kent Island, Maryland, United States
Balcony/Patio
Vio.com
Details
Resort  Chester
from $107 per night
Resort ∙ 2 guests ∙ 1 bedroom
Chester, Kent Island, Maryland, United States
Balcony/Patio
Vio.com
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 $105 per night.

Is it possible to find vacation rentals in Chester?

Tripping.com offers great selection on vacation rentals with 183 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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