Chester Summer Rentals, Cottages & Cabins
Book a Place to Stay in Chester for Your Summer Getaway
- Air Conditioner
- Parking
- TV
- Parking
- Pool
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- TV
- Parking
- Accessibility
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- View
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Pet Friendly
- View
- Security/Safety
- Child Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
About Chester Summer Rental on PickleTrip
PickleTrip™'s summer rentals in Chester are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.
Enjoy the perfect summer vacation in Chester with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.
Frequently Asked Questions About Chester Luxury Rentals
There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Chester:
- Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
- Secluded Private Cabin with Pool, hot tub, fireplace & so much more
- The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
- Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
- "Little Brick House on Main (1865)”
- Lodge at the Longbranch next to the Longbranch Saloon
- Cottage w/Yard, Walk to Historic Attractions
- Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
- Log Lodge - Secluded - Private Pool - Game Room - WiFi - 1 Hr South of St.Louis
- ⚜️Rivertown Retreat⚜️ Lewis & Clark: King BednSleeps 4
Yes, here are some popular summer holiday rentals in Chester that have a private or indoor pool:
- "Little Brick House on Main (1865)”
- Missouri Castle with Private Lake, Pool and 100 Acres!
- Holiday Inn Express & Suites Perryville by IHG
- Lodge at the Longbranch next to the Longbranch Saloon
Check all holiday rentals with a pool in Chester on PickleTrip.
Yes, We have 63 summer rental homes in Chester and types of place to stay in Chester include:
- Vacation Homes: 63 available for rent
- Villas: 63 Rentals available for rent
- Holiday Apartments: 63 Rentals available for rent
- Hotels with Suites: 63 Rentals available for book
