Charlestown Holiday Rentals

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Check prices for these dates

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Charlestown holiday rentals

Exterior
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is HK$545
HK$866 total
includes taxes & fees
29 Dec - 30 Dec
Country Get Away 1 Bedroom Apartment
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is HK$630
HK$1,922 total
includes taxes & fees
29 Dec - 30 Dec
Historic Chesapeake City Stay
1 bedroom
Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
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."
United States
Rees L.
The price is HK$644
HK$1,276 total
includes taxes & fees
14 Jan - 15 Jan 2026
Summer Rustic Camping with AC and King Bed
Fridge, microwave, oven, stovetop
Quarry Landing - Center of Town & River View - 3 Bedroom

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, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,152
HK$1,798 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom
Smart TV
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

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
Elkton
9.8 out of 10, Exceptional, (7)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$934
HK$1,254 total
includes taxes & fees
24 Dec - 25 Dec
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (31)
"The River Cottage is very charming, cozy, and well-stocked with all the essentials. The host is quick to respond to inquiries. We had a wonderful and relaxing stay!"
United States
Xiaodong F.
The price is HK$1,366
HK$1,612 total
includes taxes & fees
24 Dec - 25 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior
Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is HK$1,348
HK$3,474 total
includes taxes & fees
5 Jan - 6 Jan 2026
Thunder Hill Retreat - Spacious/Deck/Hot tub
Interior
Small House on Gentleman’s Farm

Small House on Gentleman’s Farm

Small House on Gentleman’s Farm
Bel Air
10.0 out of 10, Exceptional, (13)
"Great little getaway, very clean, and the bedding was so comfy! "
United States
Joan F.
The price is HK$1,002
HK$2,499 total
includes taxes & fees
28 Dec - 29 Dec
Small House on Gentleman’s Farm
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

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is HK$1,050
HK$2,656 total
includes taxes & fees
1 Jan - 2 Jan 2026
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Interior
Cozy loft above ink shop

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.6 out of 10, Exceptional, (5)
"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."
United States
Krystle M.
The price is HK$716
HK$904 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy loft above ink shop
Interior
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.2 out of 10, Very good, (12)
"Nice and quiet place to stay"
United States
Gary M.
The price is HK$1,050
HK$2,186 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Interior
Hobbit House one of a kind home

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
The price is HK$885
HK$2,300 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hobbit House one of a kind home
Dining
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

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (21)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is HK$1,527
HK$2,607 total
includes taxes & fees
30 Dec - 31 Dec
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Dining
Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is HK$1,751
HK$3,241 total
includes taxes & fees
30 Dec - 31 Dec
Grandma’s Cottage will wrap around you like a warm hug
Smart TV, table football, books
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is HK$1,401
HK$2,606 total
includes taxes & fees
24 Dec - 25 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Interior
Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is HK$1,089
HK$1,955 total
includes taxes & fees
24 Dec - 25 Dec
Private 3 room Queen Suite w/Kitchenette
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

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
2.0 star property
Nottingham
9.2 out of 10, Wonderful, (13)
"We had an excellent stay"
United States
Meagan
The price is HK$1,233
HK$1,792 total
includes taxes & fees
25 Dec - 26 Dec
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Terrace/patio
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

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
Newark
10.0 out of 10, Exceptional, (4)
"Enjoyed our stay."
United States
Erik H.
The price is HK$1,118
HK$2,106 total
includes taxes & fees
14 Jan - 15 Jan 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is HK$1,348
HK$1,554 total
includes taxes & fees
29 Dec - 30 Dec
High Tide Haven Suite
Outdoor dining
Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
2.0 star property
Nottingham
The price is HK$949
HK$1,620 total
includes taxes & fees
13 Jan - 14 Jan 2026
Amish Countryside Escape at Forest Edge Farm
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

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"The room was new and clean. The pool was small but did the trick. Staff was kind "
Richard 1-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Middletown

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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Charlestown is located on a river, and has a patio, a garden 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 can relax into your holiday with a selection of games and 1 hot tub.

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 Plumpton Park Zoo, 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.