Holiday Homes in Charlestown

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Featured Holiday Homes in Charlestown

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

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

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."
The price is AU$711
includes taxes & fees
2 Dec - 3 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants

Beautiful Colonial Style Home in Nottingham PA

9.8 out of 10, Exceptional, (6)
"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."
Beautiful Colonial Style Home in Nottingham PA

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River

Ultimate Retreat @ Papermill Rd

8.8 out of 10, Excellent, (5)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd

Sweet Little Home Away From Home, North East, MD

10.0 out of 10, Exceptional, (4)
"My family enjoyed our stay at Angela's house in North East. The house was clean, beds were comfortable, kitchen had what we needed. We'd stay there again."
Sweet Little Home Away From Home, North East, MD

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

9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook

Christiana Home

The price is AU$772
includes taxes & fees
2 Dec - 3 Dec
Christiana Home

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (6)
"This was a wonderful home. The amenities were great, the home was clean and the communication couldn't have been better. "
Spacious North East Home w/ Fenced Yard & Fire Pit

White Clay Creek Cottage

10.0 out of 10, Exceptional, (1)
"The house was beautiful and nice. Only the way in and out posed any issue. Would definitely stay again. Perfect location and close to everything in the area. Lots of beautiful colors."
The price is AU$307
includes taxes & fees
1 Dec - 2 Dec
White Clay Creek Cottage

Tip Of The Town Fresh and New 3 Bedroom Nest

9.8 out of 10, Exceptional, (7)
"Loved the convenience to the town of South East and Blue Elk Vineyard. The property was very clean. Having an EV charger was so helpful."
The price is AU$567
includes taxes & fees
2 Dec - 3 Dec
Tip Of The Town Fresh and New 3 Bedroom Nest

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub

Charming 3-bedroom house with AC and WiFi in fabulous Newark

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a perfect place for family to stay during our wedding. The house was very clean and very well maintained. Would definitely recommend to anyone. Thanks again for letting us use your home. "
Charming 3-bedroom house with AC and WiFi in fabulous Newark

Luxurious and spacious townhome with all necessary amenities awaits your stay.

10.0 out of 10, Exceptional, (3)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

The Riverside Oasis waterfront with hot tub

10.0 out of 10, Exceptional, (1)
"We had a great weekend! The house was amazingly decorated. All the furnishings were comfy and soft. We loved it. There were plenty of games both indoor and outdoor to keep everyone busy. The views from pretty much every room were stunning. Can’t wait to come back!"
The Riverside Oasis waterfront with hot tub

River Haven with Hot Tub | 4 Bed, 3.5 Bath

9.8 out of 10, Exceptional, (22)
"Very secluded and a great house for a family reunion."
River Haven with Hot Tub | 4 Bed, 3.5 Bath

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

9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
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

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

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.