Find Vacation Rentals in Chester

We have 76 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
$585 per night
House ∙ 12 guests ∙ 5 bedrooms
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
House Chester
$379 per night
House ∙ 9 guests ∙ 5 bedrooms
5.0
Outstanding (8 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
Villa Chester
$512 per night
Villa ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding (2 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
House Chester
$1,007 per night
House ∙ 14 guests ∙ 6 bedrooms
4.3
Very good (34 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
House Chester
$288 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (58 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
House Chester
$700 per night
House ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding (41 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
Apartment Chester
$143 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (56 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
Villa Chester
$552 per night
Villa ∙ 16 guests ∙ 6 bedrooms
4.0
Very good (2 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
Details
Details
House Chester
$569 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (25 ratings)
Chester, Orange County, New York, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Chester
$1,998 per night
House ∙ 24 guests ∙ 10 bedrooms
Chester, Orange County, New York, United States
Pool
Details
Vrbo
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Cottage  Chester
$1,034 per night
Cottage ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (4 ratings)
Chester, Orange County, New York, United States
Pool
Details
Vrbo
Details
Details
Villa  Chester
$1,038 per night
Villa ∙ 16 guests ∙ 7 bedrooms
4.5
Excellent (12 ratings)
Chester, Orange County, New York, United States
Pool
Details
Vrbo
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Pet-Friendly Homes and Apartments

Lodge  Chester
$1,002 per night
Lodge ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding (4 ratings)
Chester, Orange County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chester
$894 per night
House ∙ 10 guests ∙ 3 bedrooms
4.9
Outstanding (71 ratings)
Chester, Orange County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chester
$388 per night
House ∙ 11 guests ∙ 5 bedrooms
4.4
Very good (17 ratings)
Chester, Orange County, New York, United States
Pet-friendly
Details
Vrbo
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Vacation Homes With Terraces

House  Chester
$360 per night
House ∙ 6 guests ∙ 4 bedrooms
4.5
Excellent (4 ratings)
Chester, Orange County, New York, United States
Balcony/Patio
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Vrbo
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Farmhouse  Chester
$347 per night
Farmhouse ∙ 10 guests ∙ 4 bedrooms
Chester, Orange County, New York, United States
Balcony/Patio
Details
Vrbo
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House  Chester
$80 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (6 ratings)
Chester, Orange County, New York, United States
Balcony/Patio
Details
Vrbo
Details
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 $128 per night.

How many vacation rentals are available in Chester?

Our large collection of vacation homes makes it easy to filter and compare 76 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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