Charlestown Holiday Rentals

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Check prices for these dates

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

Holiday Rentals in Charlestown

Property grounds
Country Get Away 1 Bedroom Apartment
Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (39)
"Perfect in every way… a great stay"
Robert B.
The price is HK$544
HK$865 total
includes taxes & fees
17 Nov - 18 Nov
Country Get Away 1 Bedroom Apartment
Marina
Historic Chesapeake City Stay
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
Michael S.
The price is HK$839
HK$2,166 total
includes taxes & fees
19 Oct - 20 Oct
Historic Chesapeake City Stay
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom
Quarry Landing - Center of Town & River View - 3 Bedroom
9.8 out of 10, Exceptional, (9)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
Elise E.
The price is HK$1,150
HK$1,795 total
includes taxes & fees
4 Nov - 5 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom
1 bedroom
Summer Rustic Camping with AC and King Bed
Summer Rustic Camping with AC and King Bed
9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
Rees L.
The price is HK$652
HK$1,283 total
includes taxes & fees
20 Oct - 21 Oct
Summer Rustic Camping with AC and King Bed
Outdoor spa tub
Thunder Hill Retreat - Spacious/Deck/Hot tub
Thunder Hill Retreat - Spacious/Deck/Hot tub
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
Heidi Z.
The price is HK$1,500
HK$3,688 total
includes taxes & fees
20 Oct - 21 Oct
Thunder Hill Retreat - Spacious/Deck/Hot tub
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (27)
"Very nice cottage, as advertised"
nick k.
The price is HK$1,363
HK$1,610 total
includes taxes & fees
28 Oct - 29 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Iron/ironing board, WiFi, bed sheets
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
2.0 star property
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
Melissa J.
The price is HK$932
HK$1,252 total
includes taxes & fees
19 Oct - 20 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
1 bedroom, WiFi, bed sheets, wheelchair access
Restful Non-Shared Basement Suite In Harford MD
Restful Non-Shared Basement Suite In Harford MD
The price is HK$427
HK$865 total
includes taxes & fees
10 Nov - 11 Nov
Restful Non-Shared Basement Suite In Harford MD
Fridge, microwave, oven, stovetop
Cozy loft above ink shop
Cozy loft above ink shop
9.0 out of 10, Wonderful, (2)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
Krystle M.
The price is HK$643
HK$828 total
includes taxes & fees
23 Oct - 24 Oct
Cozy loft above ink shop
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
8.0 out of 10, Very good, (9)
"Nice and quiet place to stay"
Gary M.
The price is HK$1,049
HK$2,182 total
includes taxes & fees
18 Nov - 19 Nov
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
Anthony C.
The price is HK$1,049
HK$2,669 total
includes taxes & fees
19 Oct - 20 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Interior
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
9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
Chris J.
The price is HK$1,504
HK$2,589 total
includes taxes & fees
22 Oct - 23 Oct
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug
Grandma’s Cottage will wrap around you like a warm hug
The price is HK$1,748
HK$3,195 total
includes taxes & fees
22 Oct - 23 Oct
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
2.0 star property
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay."
Erik H.
The price is HK$1,183
HK$2,240 total
includes taxes & fees
21 Oct - 22 Oct
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Interior
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
2.0 star property
9.6 out of 10, Exceptional, (10)
"We had an excellent stay"
Meagan
The price is HK$1,231
HK$1,798 total
includes taxes & fees
30 Oct - 31 Oct
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Interior
Room #2 in Elkton, MD – Easy Access to I-95
Room #2 in Elkton, MD – Easy Access to I-95
2.0 star property
The price is HK$491
HK$767 total
includes taxes & fees
19 Oct - 20 Oct
Room #2 in Elkton, MD – Easy Access to I-95
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
10.0 out of 10, Exceptional, (4)
"The house was even better than I anticipated! It was very clean, quiet and comfy. The beds were amazing and we got the best nights sleep! Location was perfect for Ripken Experience. The owner was very helpful and quick to respond to my messages. "
Alexandra C.
The price is HK$1,301
HK$1,955 total
includes taxes & fees
20 Oct - 21 Oct
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Exterior
Private 3 room Queen Suite w/Kitchenette
Private 3 room Queen Suite w/Kitchenette
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
Hisham M.
The price is HK$979
HK$1,886 total
includes taxes & fees
27 Oct - 28 Oct
Private 3 room Queen Suite w/Kitchenette
1 bedroom, iron/ironing board, WiFi, bed sheets
High Tide Haven Suite
High Tide Haven Suite
The price is HK$1,346
HK$1,567 total
includes taxes & fees
19 Oct - 20 Oct
High Tide Haven Suite
Terrace/patio
Nature's Haven Tiny Home
Nature's Haven Tiny Home
10.0 out of 10, Exceptional, (3)
"Enjoyed"
Stephani M.
The price is HK$1,468
HK$1,806 total
includes taxes & fees
30 Oct - 31 Oct
Nature's Haven Tiny Home
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

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

10/10 Excellent
"Great staff, nice rooms, very fancy coffee machine for breakfast. Only complaint was breakfast was not stocked. Very few options and variety’s for breakfast. We ate around 8 which is the middle-ish of their breakfast hours and I feel it should have been stocked. (It wasn’t busy)"
Brody 1-night trip
Posted 2 days ago
Best Western Plus Newark/Christiana Inn

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
  • Use the map to find apartments and other holiday homes in the Charlestown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

Frequently asked questions

Can I find a holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay.

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

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Charlestown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Charlestown?

With 7 Expedia holiday rentals, you're guaranteed 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 Havre de Grace Maritime Museum, or get outside and enjoy nature at North East Beach Area. In the wider area, you’ll find Charlestown Town Hall and Hollywood Casino.

What are holiday rentals like in Charlestown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Charlestown. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a small group gathering.