Charlestown Holiday Rentals

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Charlestown holiday rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is HK$846
HK$2,183 total
includes taxes & fees
12 Apr - 13 Apr
Historic Chesapeake City Stay
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"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$550
HK$1,186 total
includes taxes & fees
12 Apr - 13 Apr
Summer Rustic Camping with AC and King Bed
Exterior

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, (40 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is HK$1,374
HK$1,623 total
includes taxes & fees
15 Apr - 16 Apr
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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
Elkton
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$940
HK$1,262 total
includes taxes & fees
22 Apr - 23 Apr
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Terrace/patio

Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (2 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 HK$388
HK$826 total
includes taxes & fees
4 May - 5 May
Restful Non-Shared Basement Suite In Harford MD
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (1 review)
The price is HK$830
HK$1,506 total
includes taxes & fees
13 Apr - 14 Apr
Amish Countryside Escape at Forest Edge Farm
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (13 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is HK$529
HK$727 total
includes taxes & fees
16 Apr - 17 Apr
Charming 2-bedroom house in Aberdeen with WiFi and AC
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is HK$2,084
HK$3,267 total
includes taxes & fees
13 Apr - 14 Apr
Long Beach Cottage, (romantic couple’s getaway)
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."
United States
Richard
The price is HK$548
HK$872 total
includes taxes & fees
12 May - 13 May
Country Get Away Studio Apartment
Outdoor dining

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is HK$981
HK$1,245 total
includes taxes & fees
12 Apr - 13 Apr
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Fridge, microwave, oven, stovetop

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 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,241
HK$1,897 total
includes taxes & fees
13 Apr - 14 Apr
Quarry Landing - Center of Town & River View - 3 Bedroom
Interior

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.6 out of 10, Exceptional, (10 reviews)
"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."
United States
Jeffrey R.
The price is HK$775
HK$967 total
includes taxes & fees
14 Apr - 15 Apr
Cozy loft above ink shop
Living area

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, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is HK$1,192
HK$1,637 total
includes taxes & fees
13 Apr - 14 Apr
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is HK$1,480
HK$1,868 total
includes taxes & fees
11 May - 12 May
Tiny Home Tranquil Oasis
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is HK$1,480
HK$1,782 total
includes taxes & fees
15 Apr - 16 Apr
Nature's Haven Tiny 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
Newark
9.6 out of 10, Exceptional, (21 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 HK$2,080
HK$3,239 total
includes taxes & fees
22 Apr - 23 Apr
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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
Nottingham
9.4 out of 10, Exceptional, (19 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveller
The price is HK$1,240
HK$1,804 total
includes taxes & fees
20 Apr - 21 Apr
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Sun-loungers, beach towels

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, (150 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is HK$2,024
HK$4,113 total
includes taxes & fees
13 Apr - 14 Apr
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"The house is very spacious with comfortable beds and numerous activities and games for the family. The hot tub was a feature we all truly enjoyed, especially while watching the snow come down.The location is very tranquil and the views are beautiful!The owner is very responsive to messages and was understanding when one of us had an issue requiring a later checkout. We would definitely book a future stay at Thunderhill!"
United States
Heather W.
The price is HK$1,714
HK$3,943 total
includes taxes & fees
15 Apr - 16 Apr
Thunder Hill Retreat - Spacious/Deck/Hot tub
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is HK$1,028
HK$1,287 total
includes taxes & fees
27 Apr - 28 Apr
High Tide Haven Suite
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

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

10/10 Excellent
"Clean rooms friendly staff "
Marketa 3-night trip
Posted 1 hour ago
Quality Inn Newark - Wilmington

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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  • 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?

Captivating Chesapeake experience: This holiday home rental outside of Charlestown is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.