Compare Chestertown Cottage Rentals

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Featured Cottages in Chestertown

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Guests staying at this cottage enjoy a sauna, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

Kitchen

Washer

Peaceful getaway convenient to local amenities including beach, boating & food

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

Secluded Cozy Cottage in Historic Downtown

$547 nightly

$624 total

Apr 8 - Apr 9

Total with taxes and fees

At this cottage, guests have access to a terrace, laundry facilities, and a garden. If you drive, put free offsite parking to good use. This smoke-free cottage also has barbecue grills.

Your Annapolis Waterfront retreat - ready for a winter getaway!

This cottage offers barbecue grills, a garden, and a picnic area.

Guests staying at this cottage can enjoy an outdoor pool, a garden, and barbecue grills.

Cozy, unique, historic registered cottage on the Corsica River!

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

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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.

Hotel Options in Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

$110 nightly

$122 total

May 3 - May 4

Total with taxes and fees

8.6/10 Excellent! (896 reviews)

Blue Heron Farm Waterfront Chalet

Chestertown MD

10/10 Exceptional! (2 reviews)

Historic Inns of Annapolis

58 State Circle Annapolis MD

$174 nightly

$198 total

Apr 19 - Apr 20

Total with taxes and fees

9/10 Wonderful! (1,870 reviews)

Cottages

Book a cottage in Chestertown
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chestertown. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chestertown better.

Cottage apartments in Chestertown range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chestertown
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chestertown and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chestertown cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chestertown. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chestertown Cottages essential information

Accommodation	60 Cottages
Lowest Price	$122
Highest Price	$624
Popular accommodation	Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly, Peaceful getaway convenient to local amenities including beach, boating & food, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Secluded Waterfront Cottage on 200 acre farm near Queenstown, Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings., Secluded Cozy Cottage in Historic Downtown, Your Annapolis Waterfront retreat - ready for a winter getaway!, The Heron's Nest at Atlantic Marina, Cozy, unique, historic registered cottage on the Corsica River!