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Compare 159 Vacation Homes in Chaptico with updated reviews, rates, and availability.

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.4 out of 10, Exceptional, (30)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Colonial Beach Cottage, 7 minutes walk to beach!

9.6 out of 10, Exceptional, (25)
"It was okay for a short stay. "
Colonial Beach Cottage, 7 minutes walk to beach!

Hawthorn House Remodeled 3BR Walk to Town!

10.0 out of 10, Exceptional, (3)
"This house has been beautifully restored and was the perfect getaway for 2 couples & 2 kids under 5. The rooms are spacious, the front porch & back deck are great outdoor spaces, and the kids loved running around the backyard and hanging in the hammocks. The linens were soft & clean & plentiful, and we had everything we needed in the kitchen & for using the grill. Also, the host was very responsive & accommodating. We literally couldn’t ask for more in a vacation rental house. Thank you for...
Hawthorn House Remodeled 3BR Walk to Town!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (63)
"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "
Inviting and Serene Home on Monroe Bay Creek

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is SAR 844
SAR 2,208 total
includes taxes & fees
24 Feb - 25 Feb
4-BR Waterfront Turret Home

Spectacular Waterfront Retreat with Pier

10.0 out of 10, Exceptional, (7)
"Classic cottage, very clean and well-supplied. Comfy bed in main bedroom! Beautiful property on the river - quiet and peaceful. Lovely sitting areas both inside and out. Restorative!"
Spectacular Waterfront Retreat with Pier

PRIVATE BEACHFRONT STUNNING HOME, FOSSILS, 450 PIER, MILES OF HIKING TRAILS

10.0 out of 10, Exceptional, (112)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
PRIVATE BEACHFRONT STUNNING HOME, FOSSILS, 450 PIER, MILES OF HIKING TRAILS

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!

10.0 out of 10, Exceptional, (2)
"Quite and friendly neighbors "
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

9.8 out of 10, Exceptional, (10)
"Awesome property/location/amenities/host! We enjoyed every nano-second of our stay, and that is due to the host/hostess and the property they maintain and provide in the best way possible. We couldn't have wished for a better experience and hope to visit again and again. If you are planning to visit Cobb Island, this is the property you want to be at. Every inquiry before arrival was responded to promptly, and upon arrival, we were amazed at how clean and well addressed all our needs were...
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Luxury Modern Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very nice inside, love all the windows"
The price is SAR 596
SAR 1,759 total
includes taxes & fees
24 Feb - 25 Feb
Luxury Modern Waterfront Retreat

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Waterfront Lusby Escape w/ Fire Pit & Kayaks!

10.0 out of 10, Exceptional, (6)
"Our family was looking for a place to gather to visit our Aunt who lives in the area. Six of us stayed at the Waterfront Lusby home and hosted a dinner for our Aunt and cousins. There was plenty of space for our gathering in addition to the comfortable accommodations for our weekend stay. The neighbors were very friendly and welcoming."
Waterfront Lusby Escape w/ Fire Pit & Kayaks!

Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly

10.0 out of 10, Exceptional, (5)
"This property is outstanding! Absolutely spotless and host super to work with. Great neighborhood, easy walking and our dogs loved it too!"
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly

Cheerful 6 bedroom House with free parking wldf

5.0 out of 10, (2)
"Nice house in a quiet neighborhood that is huge. One upstairs room you could even put an air mattress in if needed more room. Any issues I had the owner fixed quickly. Have stayed here twice now for work and will stay again if needed. "
Cheerful 6 bedroom House with free parking wldf

Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (2)
Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi

Unplug and unwind at your Leonardtown waterfront vacation home!

8.8 out of 10, Excellent, (5)
"We were here for Thanksgiving, but were thinking the whole time that this would be a great spot in warmer weather. With the water access and spacious accommodations it would be a great basecamp."
Unplug and unwind at your Leonardtown waterfront vacation home!

Waterfront Beauty on the Bay

10.0 out of 10, Exceptional, (1)
"Nice house, well stocked kitchen and truly gorgeous sunsets right on the water. Had a great time!"
Waterfront Beauty on the Bay
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 Chaptico

Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

9.8 out of 10, Exceptional, (7)
"Great place.. quiet neighborhood.. our only regret is that the weather was to cold to enjoy it to its fullest. The sunsets are gorgeous. The host was great as well."
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (171)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
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.