Photo by Assya A

Search Cottages in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Featured Cottages in Chestertown

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 P10,725
P26,983 total
includes taxes & fees
Oct 6 - Oct 7
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
13 Mi to Downtown Baltimore: Quiet Home w/ Porch
Interior

13 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
13 Mi to Downtown Baltimore: Quiet Home w/ Porch
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
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
Baltimore Area Vacation Rental w/ Deck!
Interior

Baltimore Area Vacation Rental w/ Deck!

3.0 star property
Baltimore Area Vacation Rental w/ Deck!
Sunny Glen Burnie Home - On-site Water Access
Interior

Sunny Glen Burnie Home - On-site Water Access

3.0 star property
Sunny Glen Burnie Home - On-site Water Access
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!
Eastern Shore Getaway: Walk to Tolchester Marina!
Exterior

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!
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
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
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!
Exterior

Pasadena Hideaway w/ Game Room & Fire Pit!

3.0 star property
Pasadena Hideaway w/ Game Room & Fire Pit!
Family-friendly Cottage, Walk to the Beach!
Exterior

Family-friendly Cottage, Walk to the Beach!

3.0 star property
Family-friendly Cottage, Walk to the Beach!
Patio & Water Views: Serene Bohemia River Escape!
Interior

Patio & Water Views: Serene Bohemia River Escape!

3.0 star property
Patio & Water Views: Serene Bohemia River Escape!
Charming Edgemere Home w/ Deck & Grill!
Property grounds

Charming Edgemere Home w/ Deck & Grill!

3.0 star property
Charming Edgemere Home w/ Deck & Grill!
Pet-friendly Home on Chester River w/ Dock!
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!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Absolutely great stay"
David 1-night trip
Posted 20 hours ago
Sagamore Pendry Baltimore

Find out more about Chestertown

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
23 Cottages
Lowest Price
P26,983
Highest Price
P26,983

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that traveling 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 favorite 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia