Find Vacation Rentals in Chester

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Popular Chester Vacation Rentals

Find the perfect Chester vacation rental

House Chester
from $2,591 per night
26 guests ∙ 10 bedrooms

House

5.0
Outstanding(8 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $433 per night
16 guests ∙ 5 bedrooms

House

4.0
Very good(6 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
Farmhouse Chester
from $369 per night
10 guests ∙ 4 bedrooms

Farmhouse

5.0
Outstanding(4 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $381 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(76 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
Apartment Chester
from $160 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

116 m² Apartment

5.0
Outstanding(60 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $357 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(7 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
Villa Chester
from $693 per night
12 guests ∙ 5 bedrooms

Villa

5.0
Outstanding(5 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $774 per night
House ∙ 11 guests ∙ 4 bedrooms

325 m² House

5.0
Outstanding(43 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
House Chester
from $348 per night
7 guests ∙ 3 bedrooms

House

4.5
Excellent(4 ratings)
Chester, Orange County, New York, United States
Vrbo
Details
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Recommended Rentals With Pools

Villa  Chester
from $869 per night
Villa ∙ 16 guests ∙ 7 bedrooms

437 m² Villa

4.6
Excellent(14 ratings)
Chester, Orange County, New York, United States
Pool
Vrbo
Details
House  Chester
from $825 per night
House ∙ 10 guests ∙ 4 bedrooms

260 m² House

5.0
Outstanding(27 ratings)
Chester, Orange County, New York, United States
Pool
Vrbo
Details
Cottage  Chester
from $1,114 per night
10 guests ∙ 5 bedrooms

Cottage

5.0
Outstanding(14 ratings)
Chester, Orange County, New York, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Chester
from $161 per night
4 guests ∙ 2 bedrooms

House

Chester, Orange County, New York, United States
Pet-friendly
Vrbo
Details
House  Chester
from $927 per night
16 guests ∙ 7 bedrooms

House

Chester, Orange County, New York, United States
Pet-friendly
Vrbo
Details
House  Chester
from $2,411 per night
House ∙ 17 guests ∙ 7 bedrooms

465 m² House

5.0
Outstanding(10 ratings)
Chester, Orange County, New York, United States
Pet-friendly
Vrbo
Details
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Vacation rentals and apartments with air conditioning

House  Chester
from $369 per night
House ∙ 11 guests ∙ 4 bedrooms

157 m² House

5.0
Outstanding(1 rating)
Chester, Orange County, New York, United States
Air conditioning
HomeToGo
Details
House  Chester
from $219 per night
House ∙ 5 guests ∙ 2 bedrooms

142 m² House

5.0
Outstanding(2 ratings)
Chester, Orange County, New York, United States
Air conditioning
Vrbo
Details
House  Chester
from $271 per night
House ∙ 6 guests ∙ 2 bedrooms

92 m² House

4.9
Outstanding(37 ratings)
Chester, Orange County, New York, United States
Air conditioning
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 97 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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