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Featured Cottages in Chestertown

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

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

Stevensville MD
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

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena MD
$583 nightly
The price is $665 total per night
$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

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3 out of 5
Rosedale MD
$431 nightly
The price is $498 total per night
$498 total
Jan 6 - Jan 7
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

Secluded Cozy Cottage in Historic Downtown

Annapolis MD
$470 nightly
The price is $536 total per night
$536 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

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

2 out of 5
Stevensville MD
$802 nightly
The price is $885 total per night
$885 total
Jan 8 - Jan 9
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
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

Annapolis MD
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
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis MD
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!

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

Centreville MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Arnold MD
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

    Comfort Inn & Suites Chestertown

    150 Scheeler Road Chestertown MD
    $95 nightly
    The price is $106 total per night from Jan 26 to Jan 27
    $106 total
    Jan 26 - Jan 27
    Total with taxes and fees
    8.4/10 Very Good! (861 reviews)
    La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

    La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

    4 Philadelphia Ct Rosedale MD
    $65 nightly
    The price is $75 total per night from Jan 11 to Jan 12
    $75 total
    Jan 11 - Jan 12
    Total with taxes and fees
    7/10 Good! (1,117 reviews)
    Pendry Baltimore

    Pendry Baltimore

    1715 Thames St. Baltimore MD
    $351 nightly
    The price is $412 total per night from Jan 19 to Jan 20
    $412 total
    Jan 19 - Jan 20
    Total with taxes and fees
    9.2/10 Wonderful! (1,003 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
$75
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.

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