Compare Vacation Rentals & Rent By Owner Homes in Chester, Connecticut, USA
About Chester Vacation Rentals
With more than 58 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 1128.72 ft² on average, with prices averaging US $512 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, CT
Frequently Asked Questions About Chester?
What are the top vacation rentals in Chester?
- Summer at the Haddam House
- COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
- Charming Chester Retreat- Near Village Center
- Updated cottage "Beriozka" on Cedar Lake
- Daniel Boone meets Mid Century Modern Retreat
- Life on the Farm
- Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.
- Quiet Killingworth Rental w/Deck & Grill!
- Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond
- Clinton's Hidden Secret Renovated 2BR Stonehouse, WiFi, AC, Beach Pass & more
How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 58 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 (2)
| Neighborhood | Property Count |
|---|---|
| Deep River Center Vacation Rentals in Old Saybrook, Connecticut | 65 |
| Chester Center Vacation Rentals in Old Saybrook, Connecticut | 60 |
