Hotels With Free Parking in Chestertown

Photo by Julie Miller

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We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking, and you save up to 60%!

Featured Chestertown Hotels with Free Parking

Friends Lake Inn
Friends Lake Inn
4 out of 5
963 Friends Lake Rd, Chestertown, NY
Stay at this 4-star hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ...
Friends Lake Inn
Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
2 out of 5
5537 State Route 8, Chestertown, NY
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ...
Pine Tree Motel & Cabins
The Fern Lodge
The Fern Lodge
3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY
Stay at this 3.5-star beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ...
The Fern Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels with Free Parking in Chestertown

You’re always looking to save a buck here or there. If you can squeeze into that teeny-weeny parallel spot on the side street to avoid feeding the meter, you’ll do it. But it sure would be nice to pull into your hotel without pulling some vehicular gymnastics to do so. We have a free spot saved for you on your next trip to Chestertown. When you choose hotels with free parking in Chestertown you can leave all those parking woes and fees behind.

How great is this space?

If you’re staying in Chestertown for an extended weekend or a long vacation, those parking fees can add up. But when you book a Chestertown hotel with free parking, convenience is just steps away. You’ll have more time to explore, and more cash to explore with. If you’re staying downtown, you’ll value that free parking spot even more. While everyone else is circling the streets, you’ll already be onto your next adventure.

You know your car will be taken care of, but what about you? We have hotels to fit any style of traveler. From just the basics to luxury living, you’re sure to find a hotel that suits your needs with free parking to boot. You can sort hotels by:

  • Price: Want to do this trip on the cheap? We have hotels for low prices to help you save where it counts, starting at $261.

  • Amenities: Are you more of an economy or premium type? Choose hotels that have just the basics to ones that make you never want to leave. Indoor pool? On-site bistro? Spa service? Yes, please!

  • Hotwire Hot Rate: We’ll tell you the name of the hotel after you book. It’s like going to the hippest part of town on a Saturday night and not even worrying if there’ll be parking.

No more wondering where to stay in Chestertown with a car during your next trip. We did the work for you. You can take those hard-earned dollars you used to save for keeping your car cozy and put them right back in your wallet. Next trip, parking is on them when you book a Chestertown hotel with free parking.