Chester Cottage Rentals & Holiday Homes
Find the best cottages in Chester - We found 16 exact matches
About Chester Luxury Rental on Stay If You Dare
Searching for cottages to rent near Chester? Stay If You Dare features more than 16 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Chester have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Stay If You Dare’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Chester.
Are you planning to travel to the lakeside, beach, or mountain area? Stay If You Dare’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Stay If You Dare boasts of 16 holiday cottages and places to stay in Chester. The site provides unique Airbnb, VRBO, Stay If You Dare-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Chester Cottage Rentals
How much does it cost to rent a cottage in Chester?
The average cost for a cottage rental in Chester is $235 per night. Stayifyoudare has a wide list of great cottages near Chester that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Chester that allow pets?
Yes, here are the top cottage rentals in Chester that allow you to bring your pet:
- Cozy cottage by the river perfect for nature lovers & pet friendly
- Oceanfront Garden Cottage - Gateway to Attractions and Towns, Private Cove Mooring
- Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
- Cooperage Cottage - Peaceful & Family Friendly, Oceanfront
See all pet-friendly vacation rentals in Chester on Stayifyoudare
Do you have any rental cottages in Chester that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chester to find one that works for you.
Are there quality cottages in Chester that have indoor swimming pools?
As of 2026, the data from Stayifyoudare shows that there are Over 16 private swimming pools or cottages with indoor pools in the Chester area along with other great amenities.
Do any cottages in Chester have hot tubs?
About 16 cottages in Chester boast of premium hot tubs. Some of the popular places to stay with hot tubs include:
See all holiday vacation rentals in Chester on Stayifyoudare