Charlestown Vacation Rentals
Charlestown Vacation Rentals
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
1 mi
55 rentals in Charlestown.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Bonfire by the Creek!!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Comfy, Cozy & Perfect!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Quiet & Private with Fire Pit Out Back!
Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Enjoy Birdwatching from the Deck!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Waterfront Sailor's River Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Pool House by the North East River
Rental Home
2 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
Captivating Chesapeake experience
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Waterfront house with amazing views Top of the Chesapeake, MD's best kept secret
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Top of the Chesapeake - Minutes from Historic Charlestown
Rental Home
5 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
Check in
Check out
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Water View House in Charlestown, MD
Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Charming Cottage in Historic Charlestown, MD - Marina & Beach Access
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Sandy Cove - Third East Handicap Accessible
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Bay Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Center Parlor Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third East Standard Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Conference Handicap Accessible Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Standard Deluxe King
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Conference Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Bay Standard Deluxe Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Log Cabins
Cabin
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third East Standard Suite
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Conference Family Deluxe Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First East Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Bay Deluxe Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Standard Deluxe Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Conference Standard Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Deluxe Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Standard Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Bay Master Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Bay Standard Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First East Standard Suite
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Master Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Conference Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Handicap Accessible Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second East Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second East Standard Suite
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Standard Suite
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second East Standard Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Master Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Conference Family Deluxe Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Standard Deluxe Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Family Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Standard Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Second Bay Standard Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Conference Standard Deluxe
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - Third Bay Family Deluxe Bay View
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Deluxe Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove - First Bay Standard Suite Bay View
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Showing results 1-50 of 55
Frequently Asked Questions about Charlestown
- Yes, here are some popular vacation rentals in Charlestown that have a pool:See all vacation rentals with a pool in Charlestown on Tripadvisor
- Yes, here are some popular vacation rentals in Charlestown that have internet access:See all vacation rentals in Charlestown on Tripadvisor
- The best pet friendly rentals in Charlestown are:See all pet friendly vacation rentals in Charlestown on Tripadvisor
- Some of the most popular kid friendly rentals in Charlestown are:See all kid friendly vacation rentals in Charlestown on Tripadvisor