Vacation rentals in Chesapeake Ranch Estates-Drum Point

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Popular amenities for Chesapeake Ranch Estates-Drum Point vacation rentals

Stay near Chesapeake Ranch Estates-Drum Point's top sights

The Tiki Bar23 locals recommend
The Lighthouse Restaurant and Dockbar30 locals recommend
Ruddy Duck Brewery & Grill14 locals recommend
The Island Hideaway31 locals recommend
The CD Cafe25 locals recommend
The Pier Restaurant39 locals recommend

Other great vacation rentals in Chesapeake Ranch Estates-Drum Point

Guest favorite
A sunlit corner of a room features large windows offering views of the waterfront and lush greenery. A spacious bed with a textured white coverlet is in the foreground, complemented by a yellow accent chair and a small round table set up beside a work desk.
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars1 month ago
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.
Guest favorite
A spacious screened porch features several white wicker chairs surrounding a coffee table. Ceiling fans rotate overhead while large windows provide expansive views of the water. The area includes a dining table and some colorful beach towels neatly organized on the wall.
Home in Montross
4.93 out of 5 average rating, 202 reviews

The Glebe

Irma VRating, 5 stars2 weeks ago
We loved the open space concept in the house. It has beautiful views and a fire pit. Beds were clean and comfortable. Very well supplied kitchen. We will come back. Thanks,
Superhost
A serene waterfront view is captured at dusk, with the moon reflecting on the calm water surface. Silhouetted trees frame the scene, enhancing the tranquility of the natural setting. The horizon showcases a subtle play of colors as night approaches.
Home in Lusby
4.89 out of 5 average rating, 37 reviews

Waterfront home with three bedrooms,3 full baths

JoyceRating, 5 stars3 weeks ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Guest favorite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars3 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Guest favorite
A pair of glass French doors provides a view of the outdoor seating area and pool. Bright red chairs are positioned around a fire pit on a stone patio, framed by a lush green lawn leading to the water.
Home in Tilghman Island
4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

RonnieRating, 5 stars3 months ago
Absolutely beautiful home! highly recommend!
Guest favorite
A spacious parking area is visible in front of a single-story house, surrounded by large trees. The building features a welcoming porch and two garage doors. An expansive blue sky complements the serene outdoor setting.
Home in Leonardtown
4.87 out of 5 average rating, 15 reviews

Garden Getaway

LindsayRating, 5 stars2 months ago
We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!
Guest favorite
A hammock is suspended between two trees, providing a shaded spot near the waterfront. In the background, a wooden pier extends into the water, along with a yellow kayak partially visible along the shoreline. A calm, clear view of the water and distant boats is presented.
Cottage in Leonardtown
4.92 out of 5 average rating, 143 reviews

Breton Breeze

PailinRating, 5 stars2 weeks ago
If you’re looking for a peaceful place to restore your soul and allow you to reconnect with nature, you’ll love Jan’s cozy waterside cottage. Beautifully decorated and well equipped, you’ll find everything you need provided for your stay. Thanks to Jan for sharing this special place!
Guest favorite
A two-story gray house is depicted with large arched windows and a welcoming front porch. The structure sits on stilts above the water, while a wooden dock extends towards it, surrounded by quiet water and greenery. The sky displays soft evening light.
Home in Scotland
5 out of 5 average rating, 29 reviews

Bay Front Beach House

NicholasRating, 5 stars2 weeks ago
Wow what a view. Family had a wonderful stay. House is big and well equipped. Internet is strong and plenty of hot water for all. House has access to a private beach that the small grandkids enjoyed. Definitely would stay again.

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