Holiday Homes in Charlestown

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Featured Holiday Homes in Charlestown

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Outdoor dining
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (52)
"Nice. Close to downtown. Great backyatd"
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Sweet Little Home Away From Home, North East, MD
Microwave, oven, stovetop, dishwasher
Sweet Little Home Away From Home, North East, MD
10.0 out of 10, Exceptional, (1)
"Top notch experience. "
Sweet Little Home Away From Home, North East, MD
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (93)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake
Captivating Chesapeake experience
Beach
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (249)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
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, (34)
"Debbie was a great communicator and very generous with allowing us to check in early - such a treat! The kitchen is well appointed and we were all impressed with the great bath towels and bed linens. The one thing to point out is that while this is a water front property, I didn't realize from the pictures, that its on a cliff, so you couldn't fish from the front of the property like I was imagining prior to arriving; luckily the walk to the beach was a short one so our kiddos fished from...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Top of the Chesapeake - Minutes from Historic Charlestown
View from property
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (133)
""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...
The price is AU$955
includes taxes & fees
8 Oct - 9 Oct
Top of the Chesapeake - Minutes from Historic Charlestown
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
A heated pool
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
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, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (95)
"Older home that was very clean. met our needs well. was close to the University of Delaware. "
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Chesapeake City Quiet Overlook
Outdoor dining
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (11)
"My wife and I booked Jane’s house for our wedding weekend in Chesapeake city. Jane allowed us to use her property for our wedding of 40 ppl. She could not have been nicer or more accommodating for this special occasion. She responded to all of our questions quickly and even made special offers to make our wedding weekend even more special. I cannot say enough nice things about Jane. The house and property were gorgeous in a really great location along the canal in Chesapeake city. The views...
Chesapeake City Quiet Overlook
Amazing Waterfront Home on the Bush River
Terrace/patio
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (17)
"We stayed here for our wedding weekend leading up to the big day with our families and this couldn't have asked for a better location and place to relax."
Amazing Waterfront Home on the Bush River
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, (20)
"Phyllis’ home was 100% newly remodeled and impeccably clean! We enjoyed a wonderful stay in her comfortable home. The fresh flowers were a welcome surprise after a long drive, and Phyllis checked in on us via text to make sure we made it there safely. Recommend! "
Clean and Cozy 2 BR home blocks away from downtown
Ultimate Retreat @ Papermill Rd
Aerial view
Ultimate Retreat @ Papermill Rd
10.0 out of 10, Exceptional, (4)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Historic home in the heart of Main Street- walkable to shops and restaurants
Interior
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
Historic home in the heart of Main Street- walkable to shops and restaurants
Sunset River Cottage encapsulates nautical romance.
Property grounds
Sunset River Cottage encapsulates nautical romance.
8.8 out of 10, Excellent, (10)
"Great view and cute cottage"
Sunset River Cottage encapsulates nautical romance.
Upper Chesapeake Getaway - Newly Renovated
Property grounds
Upper Chesapeake Getaway - Newly Renovated
9.8 out of 10, Exceptional, (12)
"We had a fabulous time and want you to come and decorate all of our homes! Just beautiful! The only suggestion is maybe swap out that thermostat for a simpler one. We spent way too much time fussing with that. Thank-you for everything!!! We’ll be back!! "
Upper Chesapeake Getaway - Newly Renovated
Christiana Home
Smart TV
Christiana Home
The price is AU$726
includes taxes & fees
3 Oct - 4 Oct
Christiana Home
Your perfect Maryland escape awaits!
3 bedrooms, desk, iron/ironing board, free WiFi
Your perfect Maryland escape awaits!
10.0 out of 10, Exceptional, (3)
"Our group had another great stay. The house is exactly as pictured and the host is very responsive. Everything was perfect from checkin to departure. We will definitely stay at this house again!! "
Your perfect Maryland escape awaits!
Spacious North East Home w/ Fenced Yard & Fire Pit
Terrace/patio
Spacious North East Home w/ Fenced Yard & Fire Pit
10.0 out of 10, Exceptional, (3)
"We came to town for a lacrosse tournament. Easy to get to the fields from this location. Our two families were so happy with the wonderful home and the spaces were fantastic! The towels are so soft. The photos do not do justice to the space and welcoming feeling you get. We were pleasantly pleased with our stay! Walking distance to fun restaurant and not too far from town. We would love to come back some time. Thanks for sharing your home."
Spacious North East Home w/ Fenced Yard & Fire Pit
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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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Other property types in Charlestown

Waterfront Historical District Home Near River
Fridge, microwave, stovetop, dishwasher
Waterfront Historical District Home Near River
10.0 out of 10, Exceptional, (6)
"House has recently been recently renovated and is beautiful and very comfortable!! Owners have gone above and beyond to make you comfortable. Definitely a rebook for me!! Convenient location as well, convenience store and restaurant walking distance. Live music at the restaurant certain nights. I’m amazed how they got those comfortable beds upstairs!!"
Waterfront Historical District Home Near River
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Terrace/patio
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (73)
"A hidden gem! Beautiful location on the bay with the cutest town!!! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Captivating Chesapeake experience
Beach
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (249)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
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.