Find Vacation Rentals in Chester

We have 103 properties to choose from
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Popular Chester Vacation Rentals

Find the perfect Chester vacation rental

Farmhouse Chester
from $346 per night
Farmhouse ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(3 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $516 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(32 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $300 per night
House ∙ 11 guests ∙ 5 bedrooms
4.2
Very good(22 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $536 per night
House ∙ 9 guests ∙ 5 bedrooms
4.8
Outstanding(14 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $317 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(68 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
Villa Chester
from $511 per night
Villa ∙ 14 guests ∙ 7 bedrooms
3.9
Good(7 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
Villa Chester
from $478 per night
Villa ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding(2 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
Apartment Chester
from $146 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(58 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $296 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding(16 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
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Vacation rentals and apartments with air conditioning

House  Chester
from $376 per night
House ∙ 7 guests ∙ 3 bedrooms
4.5
Excellent(2 ratings)
Chester, Orange County, New York, United States
Air conditioning
Vrbo
Details
House  Chester
from $546 per night
House ∙ 9 guests ∙ 5 bedrooms
Chester, Orange County, New York, United States
Air conditioning
Vrbo
Details
House  Chester
from $515 per night
House ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding(41 ratings)
Chester, Orange County, New York, United States
Air conditioning
Vrbo
Details
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Vacation rentals with Wi-Fi

House  Chester
from $358 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(4 ratings)
Chester, Orange County, New York, United States
Internet
Vrbo
Details
Cottage  Chester
from $1,079 per night
Cottage ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(12 ratings)
Chester, Orange County, New York, United States
Internet
Vrbo
Details
House  Chester
from $564 per night
House ∙ 16 guests ∙ 6 bedrooms
3.3
(16 ratings)
Chester, Orange County, New York, United States
Internet
Vrbo
Details
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Apartments and vacation rentals with a kitchen

House  Chester
from $339 per night
House ∙ 6 guests ∙ 4 bedrooms
Chester, Orange County, New York, United States
Kitchen
HomeToGo
Details
House  Chester
from $323 per night
House ∙ 16 guests ∙ 5 bedrooms
4.0
Very good(4 ratings)
Chester, Orange County, New York, United States
Kitchen
Vrbo
Details
Villa  Chester
from $654 per night
Villa ∙ 16 guests ∙ 6 bedrooms
4.5
Excellent(4 ratings)
Chester, Orange County, New York, United States
Kitchen
Vrbo
Details
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Frequently Asked Questions

How much does it cost to book a vacation rental in Chester?

Vacation rentals in Chester are priced starting at $143 per night.

How many vacation rentals are available in Chester?

Our large collection of vacation homes makes it easy to filter and compare 103 offers 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 Glenmere

Looking for the perfect vacation rental for your Glenmere getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Glenmere offers 151 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 143 properties with high-speed WiFi Internet, 0 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Glenmere has 151 gorgeous homes with 95 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com. Search properties from 5 vacation rental sites in Glenmere where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 100 HomeAway rentals, 44 TripAdvisor short term rentals and 3 Booking.com vacation rentals.

Popular Day Trips Near Chester

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