Find Vacation Rentals in Chester

We have 186 properties to choose from
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Popular Chester Vacation Rentals

Find the perfect Chester vacation rental

House Chester
from $258 per night
House ∙ 14 guests ∙ 4 bedrooms

204 m² House

5.0
Outstanding(38 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $421 per night
House ∙ 8 guests ∙ 4 bedrooms

232 m² House

5.0
Outstanding(138 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
Farmhouse Chester
from $304 per night
8 guests ∙ 3 bedrooms

Farmhouse

5.0
Outstanding(6 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
Houseboat Chester
from $146 per night
2 guests ∙ 1 bedroom

Houseboat

5.0
Outstanding(38 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
Houseboat Chester
from $130 per night
4 guests ∙ 2 bedrooms

Houseboat

5.0
Outstanding(131 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $689 per night
9 guests ∙ 4 bedrooms

House

5.0
Outstanding(41 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $1,866 per night
House ∙ 16 guests ∙ 7 bedrooms

531 m² House

4.5
Excellent(20 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $366 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(16 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
House Chester
from $538 per night
10 guests ∙ 4 bedrooms

House

4.9
Outstanding(16 ratings)
Chester, Kent Island, Maryland, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Chester
from $1,864 per night
House ∙ 16 guests ∙ 7 bedrooms

531 m² House

4.4
Very good(16 ratings)
Chester, Kent Island, Maryland, United States
Pool
Vrbo
Details
Resort  Chester
from $165 per night
2 guests ∙ 1 bedroom

Resort

Chester, Kent Island, Maryland, United States
Pool
Vio.com
Details
House  Chester
from $472 per night
8 guests ∙ 4 bedrooms

House

4.9
Outstanding(72 ratings)
Chester, Kent Island, Maryland, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Chester
from $708 per night
House ∙ 9 guests ∙ 3 bedrooms

313 m² House

Chester, Kent Island, Maryland, United States
Pet-friendly
HomeToGo
Details
House  Chester
from $365 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(10 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Vrbo
Details
House  Chester
from $688 per night
9 guests ∙ 4 bedrooms

House

5.0
Outstanding(38 ratings)
Chester, Kent Island, Maryland, United States
Pet-friendly
Vrbo
Details
Show more

Vacation rentals with a balcony

House  Chester
from $184 per night
2 guests ∙ 1 bedroom

House

5.0
Outstanding(77 ratings)
Chester, Kent Island, Maryland, United States
Balcony
Vrbo
Details
Apartment  Chester
from $173 per night
2 guests ∙ 1 bedroom

Apartment

Chester, Kent Island, Maryland, United States
Balcony
Vrbo
Details
Condo  Chester
from $276 per night
6 guests ∙ 3 bedrooms

Condo

4.6
Excellent(13 ratings)
Chester, Kent Island, Maryland, United States
Balcony
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 $162 per night.

Is it possible to find vacation rentals in Chester?

Tripping.com offers great selection on vacation rentals with 186 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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