Holiday Homes in Charlestown

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Featured Holiday Homes in Charlestown

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (1)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Easy check in process. House very clean. Going location. "
Chesapeake Bay House with Dock & Private Beach
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor spa tub

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (52)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay
Stay & Play at Our Beautiful Retreat located close to Fair Hill MD
Pool

Stay & Play at Our Beautiful Retreat located close to Fair Hill MD

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat located close to Fair Hill MD
5-bedroom vacation home 5 minutes from historic Charlestown
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is AU$850
includes taxes & fees
9 Sept - 10 Sept
5-bedroom vacation home 5 minutes from historic Charlestown
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Interior

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

2.0 star property
9.6 out of 10, Exceptional, (7)
"We had an excellent stay"
The price is AU$362
includes taxes & fees
3 Sept - 4 Sept
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (62)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (179)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (166)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Beach nearby

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

9.8 out of 10, Exceptional, (17)
"Enjoyed our stay. Location is beautiful and peaceful! Great place for a large group."
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Hobbit House one of a kind home
Property grounds

Hobbit House one of a kind home

10.0 out of 10, Exceptional, (6)
"Our family had a fantastic weekend here. The house fit our needs and was very relaxing and enjoyable."
Hobbit House one of a kind home
Clean and Cozy 2 BR home blocks away from downtown
Fridge, microwave, oven, stovetop

Clean and Cozy 2 BR home blocks away from downtown

10.0 out of 10, Exceptional, (28)
"Excellent Host, Phyllis goes above and beyond. Home is well maintained."
Clean and Cozy 2 BR home blocks away from downtown
Modern cozy get-away* game room-amish country
TV, fireplace

Modern cozy get-away* game room-amish country

10.0 out of 10, Exceptional, (3)
"Quiet, bucolic. House was spotless and well-organized and provisions. Hosts were both available and helpful and supportive. I would definitely stay there again. "
Modern cozy get-away* game room-amish country
Waterfront Lodge packed with Amenities
Pool

Waterfront Lodge packed with Amenities

10.0 out of 10, Exceptional, (1)
"Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. "
Waterfront Lodge packed with Amenities
Summer Rustic Camping with AC and King Bed
1 bedroom

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"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."
The price is AU$287
includes taxes & fees
3 Sept - 4 Sept
Summer Rustic Camping with AC and King Bed
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (272)
"Beautiful home and setting!"
Captivating Chesapeake experience
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Marina

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (40)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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

Find out more about Charlestown

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
Accommodation
125 Holiday Homes
Lowest Price
AU$287
Highest Price
AU$850

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