Compare Chestertown Cottage Rentals

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Featured Cottages in Chestertown

The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Pasadena MD
Guests staying at this cottage can enjoy an outdoor pool, barbecue grills, and a garden.
Pool
Kitchen
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Annapolis MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming Cottage - Northeast River / Chesapeake Bay

Charming Cottage - Northeast River / Chesapeake Bay

Perryville MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Annapolis MD
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Breakfast included
Peaceful getaway convenient to local amenities including beach, boating & food

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

Rock Hall MD
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Life is better at the RIVER!--Cozy waterfront cottage

Life is better at the RIVER!--Cozy waterfront cottage

Galena MD
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Free WiFi
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

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

Stevensville MD
Guests staying at this cottage enjoy a sauna, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Annapolis MD
$472 nightly
The price is $531 total per night
$531 total
Oct 18 - Oct 19
Total with taxes and fees
This cottage offers a picnic area, barbecue grills, and a garden.
Kitchen
Free WiFi
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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

    Red Roof Inn & Suites Chestertown

    Red Roof Inn & Suites Chestertown

    160 Scheeler Rd Chestertown MD
    $72 nightly
    The price is $80 total per night from Oct 12 to Oct 13
    $80 total
    Oct 12 - Oct 13
    Total with taxes and fees
    7.2/10 Good! (506 reviews)
    The Lodge at Great Oak Landing

    The Lodge at Great Oak Landing

    22170 Great Oak Landing Rd Chestertown MD
    $124 nightly
    The price is $137 total per night from Oct 7 to Oct 8
    $137 total
    Oct 7 - Oct 8
    Total with taxes and fees
    Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    150 Scheeler Road Chestertown MD
    $103 nightly
    The price is $115 total per night from Oct 25 to Oct 26
    $115 total
    Oct 25 - Oct 26
    Total with taxes and fees

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
63 Cottages
Lowest Price
$80
Highest Price
$531
Popular accommodation
The Heron's Nest at Atlantic Marina, Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly, Charming Cottage - Northeast River / Chesapeake Bay, Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football., Peaceful getaway convenient to local amenities including beach, boating & food, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Life is better at the RIVER!--Cozy waterfront cottage, Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly, Your Annapolis Waterfront retreat for a weekend or any-day getaway!

More to Explore