Find Pet-friendly Hotels in Chester, NY from CA $451

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May 15 - May 16
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Top Chester Pet-friendly Hotels

Spacious Home with Game Room and Pool
Terrace/patio
Spacious Home with Game Room and Pool
10.0 out of 10, Exceptional, (1)
"The house was perfect for our family. Very spacious and clean. Communication with the host was great and she was very responsive."
The price is CA $451
CA $928 total
includes taxes & fees
May 21 - May 22
Spacious Home with Game Room and Pool
Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
Property grounds
Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
9.6 out of 10, Exceptional, (4)
"We had a group of 12 staying for a spring break trip to visit local sites. The house was clean, well appointed with all necessities, and the check-in process was smooth. Only regret is the weather was poor so didn’t have the opportunity to make use of the outside grounds. Plenty of space for four families with teenagers. Definitely would recommend!"
Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
Luxury in the Woods, Pool, Privacy and Peace
6 bedrooms, iron/ironing board, travel crib, WiFi
Luxury in the Woods, Pool, Privacy and Peace
8.0 out of 10, Very good, (1)
"This house is perfect for a nice group of friends or Family, we stayed over the New Year’s Eve weekend and the house was spacious for our group, with plenty of room for everyone, Ricky is super on top of the check in /out Process so that was a breeze. My only feedback would be that the house should be better equipped in relation to the number of bedrooms offered."
Luxury in the Woods, Pool, Privacy and Peace
Fun Filled Country Retreat | Gorgeous and Modern |
Terrace/patio
Fun Filled Country Retreat | Gorgeous and Modern |
8.0 out of 10, Very good, (5)
"The stay was a fantastic choice for a group getaway. The combination of a well-designed space, thoughtful amenities, and a welcoming host made this trip truly memorable. I wouldn't hesitate to recommend this property to anyone looking for a great place to stay with friends or family. We left with smiles on our faces, fond memories in our hearts, and a strong desire to return in the future."
Fun Filled Country Retreat | Gorgeous and Modern |
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's the best time of year to travel to Chester with my pet?
When you travel with your pet, keeping tabs on the weather can help you make the trip more safe and fun for everyone. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to see and do with your pet in Chester?
Known for its skiing, Chester has lots to offer visitors. See the local sights and visit Castle Fun Center and The Rock Sports Complex. While you’re there, make sure you don’t miss Museum Village and Goosepond Mountain State Park.