A marina with boats docked, a river, and a row of houses along the riverbank.

Charlestown Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Charlestown vacation rentals

Marina

1. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is ￥17,207
￥45,091 total
includes taxes & fees
Aug 17 - Aug 18
Historic Chesapeake City Stay
Exterior

2. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful property in a quiet location. Immaculate! Will definitely be back. "
United States
Mary S.
The price is ￥11,152
￥17,732 total
includes taxes & fees
Aug 31 - Sep 1
Country Get Away Studio Apartment
Exterior

3. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥19,118
￥25,669 total
includes taxes & fees
Aug 17 - Aug 18
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior

4. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (51 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is ￥27,961
￥33,692 total
includes taxes & fees
Aug 17 - Aug 18
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
TV

5. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is ￥11,471
￥15,537 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2-bedroom house in Aberdeen with WiFi and AC
Interior

6. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is ￥26,288
￥46,442 total
includes taxes & fees
Aug 17 - Aug 18
Private 3 room Queen Suite w/Kitchenette
1 bedroom, desk, WiFi, bed sheets

7. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (2 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is ￥26,288
￥30,341 total
includes taxes & fees
Aug 24 - Aug 25
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Sun loungers, beach towels

8. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (156 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is ￥51,938
￥97,612 total
includes taxes & fees
Sep 16 - Sep 17
5-bedroom vacation home 5 minutes from historic Charlestown
Smart TV

9. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
The price is ￥31,402
￥42,913 total
includes taxes & fees
Aug 18 - Aug 19
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Coffee/tea maker, fridge, microwave, oven

10. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥23,802
￥57,485 total
includes taxes & fees
Aug 25 - Aug 26
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Coffee/tea maker, fridge, microwave, oven

11. Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥32,979
￥48,468 total
includes taxes & fees
Sep 14 - Sep 15
Quarry Landing - Center of Town & River View - 3 Bedroom
Outdoor dining

12. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
8.8 out of 10, Excellent, (3 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is ￥21,030
￥36,114 total
includes taxes & fees
Aug 31 - Sep 1
Amish Countryside Escape at Forest Edge Farm
Bar (on property)

13. Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses

Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.6 out of 10, Exceptional, (21 reviews)
"Laura was very welcoming and we loved the loft! Such a charming place for a quiet get away!"
United States
Dominic L.
The price is ￥22,369
￥39,284 total
includes taxes & fees
Aug 17 - Aug 18
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Exterior

14. Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (10 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
The price is ￥24,695
￥29,723 total
includes taxes & fees
Aug 17 - Aug 18
Cozy 1-bedroom bungalow in quaint Darlington with AC
Terrace/patio

15. Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (5 reviews)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is ￥11,758
￥20,908 total
includes taxes & fees
Sep 15 - Sep 16
Restful Non-Shared Basement Suite In Harford MD
1 bedroom, iron/ironing board, WiFi (free), bed sheets

16. Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is ￥16,657
￥35,726 total
includes taxes & fees
Aug 22 - Aug 23
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Exterior

17. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is ￥35,173
￥81,048 total
includes taxes & fees
Aug 17 - Aug 18
Thunder Hill Retreat - Spacious/Deck/Hot tub
Terrace/patio

18. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is ￥30,111
￥37,521 total
includes taxes & fees
Aug 17 - Aug 18
Nature's Haven Tiny Home
Smart TV

19. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
The price is ￥22,305
￥33,233 total
includes taxes & fees
Aug 18 - Aug 19
Cozy 1-bedroom apartment in Lincoln University
Dining

20. Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (24 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is ￥30,828
￥53,087 total
includes taxes & fees
Aug 24 - Aug 25
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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 Charlestown Hotel Reviews

Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

10/10 Excellent
"Thank yhu so much the ! It’s Was very nice and clean"
Walesha 1-night trip
Posted 7 hours ago
Sonesta Select Newark Christiana Mall

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
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Look no further and take a look at our great range of rental properties in Charlestown!

Frequently asked questions

Can I find a vacation rental in Charlestown?

Yes, you can find vacation rentals near popular sights in Charlestown, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Charlestown has to offer?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This vacation home near Charlestown is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals will I find in Charlestown?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Charlestown stay.

What can I see and do in Charlestown?

While exploring the area, visit family-friendly sights like Plumpton Park Zoo, or get outside and enjoy nature at North East Beach Area. In the larger area, you’ll find Charlestown Town Hall and Upper Bay Museum.

What are vacation rentals like in Charlestown?

Vacation rentals are private accommodations you can reserve for several days or more in Charlestown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.