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Check prices for these dates

In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Browse Select Chestertown Cottages

Our top choices for Chestertown cottages

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is ฿6,093
฿15,328 total
includes taxes & fees
26 Aug - 27 Aug
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
13 Mi to Downtown Baltimore: Quiet Home w/ Porch
House (2 Bedrooms) | Interior

13 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
13 Mi to Downtown Baltimore: Quiet Home w/ Porch
Sunny Glen Burnie Home - On-site Water Access
Terrace/patio

Sunny Glen Burnie Home - On-site Water Access

3.0 star property
Sunny Glen Burnie Home - On-site Water Access
Baltimore Area Vacation Rental w/ Deck!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Baltimore Area Vacation Rental w/ Deck!

3.0 star property
Baltimore Area Vacation Rental w/ Deck!
Grasonville Home w/ Private Pool on the Water
Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Eastern Shore Getaway: Walk to Tolchester Marina!
House (5 Bedrooms) | Private kitchen | Microwave, high chair, cookware/dishes/utensils

Eastern Shore Getaway: Walk to Tolchester Marina!

3.0 star property
Eastern Shore Getaway: Walk to Tolchester Marina!
On-site Boat Dock: Queenstown Home w/ Pool & Yard!
House (5 Bedrooms) | Interior

On-site Boat Dock: Queenstown Home w/ Pool & Yard!

3.0 star property
On-site Boat Dock: Queenstown Home w/ Pool & Yard!
Walk to Lake & Boat Ramp: Central Gem in Annapolis
House (4 Bedrooms) | Interior

Walk to Lake & Boat Ramp: Central Gem in Annapolis

3.0 star property
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Rock Hall Retreat w/ Balcony Near Park & Marina!
Interior

Rock Hall Retreat w/ Balcony Near Park & Marina!

3.0 star property
Rock Hall Retreat w/ Balcony Near Park & Marina!
Near Leidos Field at Ripken Stadium: Aberdeen Home
House (3 Bedrooms) | Interior

Near Leidos Field at Ripken Stadium: Aberdeen Home

3.0 star property
Near Leidos Field at Ripken Stadium: Aberdeen Home
Pasadena Hideaway w/ Game Room & Fire Pit!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Pasadena Hideaway w/ Game Room & Fire Pit!

3.0 star property
Pasadena Hideaway w/ Game Room & Fire Pit!
Idyllic Pasadena Retreat With Garden + Hot Tub!
Interior

Idyllic Pasadena Retreat With Garden + Hot Tub!

3.0 star property
Idyllic Pasadena Retreat With Garden + Hot Tub!
Family-friendly Cottage, Walk to the Beach!
Interior

Family-friendly Cottage, Walk to the Beach!

3.0 star property
Family-friendly Cottage, Walk to the Beach!
Charming Edgemere Home w/ Deck & Grill!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Edgemere Home w/ Deck & Grill!

3.0 star property
Charming Edgemere Home w/ Deck & Grill!
Pet-friendly Home on Chester River w/ Dock!
House (4 Bedrooms) | Interior

Pet-friendly Home on Chester River w/ Dock!

3.0 star property
Pet-friendly Home on Chester River w/ Dock!
Waterfront Millington Vacation Rental w/ Hot Tub!
House (Multiple Bedrooms) | Interior

Waterfront Millington Vacation Rental w/ Hot Tub!

3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!
Peaceful Queenstown Home w/ Deck & Grill!
Interior

Peaceful Queenstown Home w/ Deck & Grill!

3.0 star property
Peaceful Queenstown Home w/ Deck & Grill!
Home w/ Game Room & Large Yard in Parkville
Interior

Home w/ Game Room & Large Yard in Parkville

Home w/ Game Room & Large Yard in Parkville
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.
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Top Chestertown Hotel Reviews

Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

10/10 Excellent
"Friendly service providers "
Shymeek 1-night trip
Posted 16 hours ago
Courtyard by Marriott Baltimore Downtown/McHenry Row

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that travelling should be stress-free, so if you're chasing cottages in Chestertown at a competitive rate, Expedia delivers. Save cash and select a wallet-friendly option surrounded by nature, or book an upmarket cottage to pamper your favourite people.
How can I find cheap cottages in Chestertown?
The simplest way to track down cheap cottages in Chestertown is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.
What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.