Compare Chestertown Cottage Rentals

Featured Cottages in Chestertown

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

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

Kitchen

Washer

Chesapeake Cottages- 2 Quaint Waterfront Retreats

$583 nightly

$665 total

Jan 6 - Jan 7

Total with taxes and fees

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

Kitchen

Washer

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

$431 nightly

$498 total

Jan 5 - Jan 6

Total with taxes and fees

At this cottage, guests have access to free WiFi in public areas. You can put free offsite parking to good use if you drive.

Kitchen

Washer

Secluded Cozy Cottage in Historic Downtown

$507 nightly

$578 total

Jan 6 - Jan 7

Total with taxes and fees

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

Kitchen

Washer

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

$802 nightly

$885 total

Jan 4 - Jan 5

Total with taxes and fees

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills. Helpful staff is there to provide concierge services, as well as offer insight about the area.

Kitchen

Washer

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

Hot Tub

Breakfast included

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

Hot Tub

Kitchen

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

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

Kitchen

Washer

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.

Pool

Kitchen

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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

$98 nightly

$109 total

Jan 25 - Jan 26

Total with taxes and fees

8.4/10 Very Good! (861 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

$72 nightly

$80 total

Jan 9 - Jan 10

Total with taxes and fees

7.2/10 Good! (424 reviews)

Historic Inns of Annapolis

58 State Circle Annapolis MD

$169 nightly

$193 total

Jan 4 - Jan 5

Total with taxes and fees

8.8/10 Excellent! (1,902 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	62 Cottages
Lowest Price	$80
Highest Price	$885
Popular accommodation	Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly, Chesapeake Cottages- 2 Quaint Waterfront Retreats, 5 Mi to Downtown Baltimore: Quiet Home w/ Porch, Secluded Cozy Cottage in Historic Downtown, Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi, Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Cozy, unique, historic registered cottage on the Corsica River!, Rare find! Chic cottage, salt water heated pool May 15-Oct15.