Compare Vacation Rentals & Rent By Owner Homes in Chester, New York, USA
About Chester Vacation Rentals
With more than 159 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 925.43 ft² on average, with prices averaging US $614 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
Chester Vacation Rental Frequently Asked Questions
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
- Lakefront retreat with stellar water views just a short drive from West.
- Amazing Home Near West Point, Shopping, Skiing and Legoland
- The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
- Luxury Mountain House: Pool, Theater & Outdoor Kitchen
- The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
- Spectacular Mansion w/Pool&Tennis
How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 159 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.
