Compare Vacation Rentals & Rent By Owner Homes in Chester, Vermont, USA
About Chester Vacation Rentals
With more than 92 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 1152.19 ft² on average, with prices averaging US $361 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, VT
Frequently Asked Questions About Chester?
What are the top vacation rentals in Chester?
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Circa 1868 Chester Home/Victorian Farmhouse-Less than 20 MIN TO OKEMO
- Log cabin near Okemo/Ludlow on 25 acres borders state forest w/trails nearby
- Vermont Charm in the 1840 Gideon Lee House
- Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
- Cheerful residential home with lots of space
- Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Amazing Custom Home on 40+ Acres
How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 92 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.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Chester Depot Vacation Rentals in Chester, Vermont | 61 |
