Compare Vacation Rentals & Rent By Owner Homes in Chester, New York, USA
About Chester Vacation Rentals
With more than 165 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Chester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Chester. Places to stay near Chester are 743.26 ft² on average, with prices averaging US $673 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Chester, NY
Frequently Asked Questions About Chester?
What are the top vacation rentals in Chester?
- Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Lakefront/Legoland/West Point Retreat Under 1 Hour From NYC! Heated pool & Spa!
- New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
- The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
- The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
- Amazing Home Near West Point, Shopping, Skiing and Legoland
- Mountain Luxury: Pool, Theater & Outdoor Kitchen
- Spectacular Mansion w/Pool&Tennis
- NEW – 2 Side-by-Side Lake Homes Sleep 17 Pet Friendly 2 Private Docks -1 hr NYC
How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 165 in the Chester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chester.
