House holiday rentals in Chesapeake Ranch Estates-Drum Point

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Popular amenities for house rentals in Chesapeake Ranch Estates-Drum Point

House rentals with a pool

Guest favourite
Home in Montross
4.97 out of 5 average rating, 89 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

CourtneyRating, 5 stars2 weeks ago
Andrea was so responsive from day 1 when I had questions about the house! We had 10 people in town for a wedding and her house was only 3 miles from the venue which was ideal! The house was clean and had nice little extra touches; the bottom floor was surprisingly spacious and perfect for hanging out! And the hot tub was a nice add also! Overall, it was a great experience!
Superhost
Home in Montross
4.92 out of 5 average rating, 208 reviews

The Glebe

KristinaRating, 5 stars2 weeks ago
We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars2 weeks ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Top guest favourite
Home in Lusby
5 out of 5 average rating, 16 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars7 months ago
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!
Guest favourite
Home in Lusby
4.91 out of 5 average rating, 81 reviews

Spacious and private waterfront, sleeps 10

MichaelRating, 5 stars2 months ago
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.
Superhost
Home in Port Republic
4.78 out of 5 average rating, 23 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

TakishaRating, 5 stars2 weeks ago
This was one of the most well equipped houses I have ever stayed in. The hosts were very easy to communicate with and responded quickly to each contact. I highly recommend this place!!
Guest favourite
Home in Lexington Park
4.93 out of 5 average rating, 86 reviews

Serenity Bay-Priv Pool-ask about 2-night stays!

JosephRating, 5 stars2 weeks ago
A really great place! Beautiful, peaceful surroundings. House was perfect for a family getaway. Kitchen was well stocked. Room layout allowed for togetherness and privacy. The fire pit was super nice and the lake was great for the kids. Highly recommend!
Top guest favourite
Home in Tracys Landing
4.99 out of 5 average rating, 213 reviews

The Little Gypsy BoHome

ColleenRating, 5 stars2 days ago
This home was the perfect way to spend a long weekend with our family and our dog! We enjoyed every amenity (the pool, the beach, the paddleboards, the sauna, the cold plunge, the grill, and even the steam shower!) and had a great time venturing into the nearby town. The home is well taken care of and you can tell that a lot of thought went into its set up. We'll definitely be back!

Weekly house rentals

Superhost
Home in Lusby
4.78 out of 5 average rating, 23 reviews

Belle of the Chesapeake Bay

KoryRating, 5 stars5 months ago
The hosts were amazing and responsive, and the house was beautiful! I would definitely stay at this home again!
Top guest favourite
Home in Hollywood
4.99 out of 5 average rating, 80 reviews

Waterfront Home: Osprey Getaway

DamarisRating, 5 stars4 days ago
⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ We came here to celebrate my daughter graduating from HS. This place is perfectly prepared and exactly as described. In a nutshell, the home is brand new and beautifully designed, yet tastefully simple, all in an amazing-looking and peaceful setting. Garrett and Lauren thought about everything. I am so used to renting AirBNBs and always having to pack extra "stuff" in case the towels end up being too thin, or the bed sheets below standards. THAT WAS NOT THE CASE here. The hosts made sure to have high-quality and clean linens, towels, appliances, furniture, mattresses, you name it... They did not cut corners, which reflects the utmost respect to guests. Wonderful experience. Thank you, Garrett and Lauren, for the awesome home, kindness, and above and beyond attention before, during, and after our stay.
Guest favourite
Home in Taylors Island
5 out of 5 average rating, 15 reviews

Holliday House

JamesRating, 5 stars3 weeks ago
nice quiet place to relax and feel right at home
Guest favourite
Home in Lusby
4.99 out of 5 average rating, 89 reviews

Waterfront with sweeping bay view & private beach

RahinRating, 5 stars3 weeks ago
We recently stayed at Colin’s Airbnb in Lusby, MD, and it was an absolute gem. Nestled right by the ocean, the home was quaint, peaceful, and filled with charm. The views and the serenity of the surroundings made our getaway feel truly special. Colin was a wonderful host—quick to respond, kind, and genuinely pleasant to chat with. When we reached out for local bakery recommendations for our daughter’s birthday cake, he gladly shared a few. We ended up choosing one and couldn’t have been happier—the cake was perfect! The home itself was cozy and comfortable. The IKEA bedding added a clean, modern touch and made for a restful night’s sleep. There was just the right amount of space for the three of us to relax and enjoy our time together. Thank you, Colin, for making our stay memorable—we’d love to return someday!
Top guest favourite
Home in Solomons
4.99 out of 5 average rating, 78 reviews

Solomons home with harbor view!

GingerRating, 5 stars1 week ago
This was our first visit to Solomon’s Island and the location of this home was perfect. Mother uses a rollator for walking and could easily walk from the house to the boardwalk daily. We spent many hours on the second floor covered deck enjoying the activity at the harbor. Terri gave us good upfront information to help us prepare for our stay. The home was clean, quiet, and comfortable.
Superhost
Home in Piney Point
4.86 out of 5 average rating, 51 reviews

2 Bedroom Cozy Beach Cottage

WillieRating, 5 stars1 month ago
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!
Top guest favourite
Home in Solomons
5 out of 5 average rating, 27 reviews

4-BR Unique Waterfront House - Your Perfect Escape

SueRating, 5 stars1 week ago
The home was perfect! Nice large kitchen and family room area. Beds were very comfortable and there was all the amenities we needed. The yard and water views were wonderful. While we didn’t get a ton of time to enjoy the property because we were attending a wedding In Lexington Park on the water, the home was perfect for getting ready for the event. We were grateful for an early check-in time. We would definitely come back!
Guest favourite
Home in Saint Leonard
5 out of 5 average rating, 5 reviews

Waterfront Home, Spectacular View & Private Beach!

MargaretRating, 5 stars3 weeks ago
We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

Private house rentals

Superhost
Home in Lusby
4.86 out of 5 average rating, 51 reviews

Spacious Lakefront Cottage w/ Private Pier

PaulRating, 5 stars1 week ago
A Great Weekend Getaway! The Lake House is a fantastic place to stay! We had three families together for a long weekend, and it was perfect for both relaxing and having fun. The teenagers especially loved kayaking and canoeing — the highlight for them. We all enjoyed gathering around the fire pit in the evenings, and the outdoor lights added a warm, cozy touch. We tried our hand at crabbing—we didn’t catch much (probably due to our lack of skills!), but it was still a fun experience. A couple of tips for future guests: * If you plan to use the oven, bring your own baking sheets as none are available. * The fridge water dispenser is very slow, so you might want to bring some bottled water or gallon jugs. Aside from those small things, everything was great. We had a fantastic time and are already looking forward to booking another stay!
Guest favourite
Home in Solomons
4.96 out of 5 average rating, 27 reviews

Solomons Yellow House - Waterfront

SheilaRating, 5 stars5 months ago
Really enjoyed holiday get away . Place was located near water with great views. We enjoyed walking around the neighborhood was quaint. The town was was pretty with water on each side with the Christmas lights at night . We truly enjoyed our relaxing stay . Would definitely book again
Guest favourite
Home in Lexington Park
5 out of 5 average rating, 8 reviews

Stunning Views, Remodeled Family-Friendly Home

MaureenRating, 5 stars1 week ago
We had a fabulous stay! So very peaceful and relaxing. We spent the whole weekend on the screened in porch enjoying the view.
Guest favourite
Home in Montross
4.91 out of 5 average rating, 22 reviews

Potomac River Getaway

SkyRating, 5 stars1 week ago
Had a great weekend in the Northern Neck here! We watched a pod of dolphins and stingrays from the backyard, enjoyed easy access to nearby parks, and had a great time cooking in the kitchen. This is seemingly a very recently renovated house, and all the towels, sheets, beds, etc. seemed brand new as well. It was super clean, super comfy, and the hosts were very responsive! I liked that the property was surrounded on one side by forest as well—it was nice and quiet and secluded. Finally, they have a super cute collection of board games disguised as old timey books. I'd definitely stay here again!
Top guest favourite
Home in Coltons Point
4.95 out of 5 average rating, 19 reviews

The Eventide at Serenity Lane

JulieRating, 5 stars3 weeks ago
What a great find! We loved our stay and enjoyed the special touches that made us feel right at home. Definitely recommend and will be back!
Superhost
Home in Leonardtown
4.91 out of 5 average rating, 32 reviews

Abells Wharf Cottage - Natural Splendor Getaway

BrianRating, 5 stars8 months ago
We enjoyed our stay at Jan's cottage. Very clean, spacious and very good amenities. Jan was very responsive and informative on local places to visit/eat. The property is beautiful and peaceful. Just what we needed to have a relaxing weekend. Will visit again, Highly recommend!
Superhost
Home in Saint Leonard
4.85 out of 5 average rating, 48 reviews

Waterfront house with private beach and pier

GilRating, 5 stars1 month ago
We had a great stay on the water at Shuran’s place. Charming house with a beautiful view, very peaceful and quiet. The house was well stocked, with everything you would need, including in the kitchen. Very nice outdoor area with plenty of opportunities to fish, go kayaking, or just relax next to the water. Highly recommend and would definitely stay again.
Top guest favourite
Home in Saint Leonard
4.95 out of 5 average rating, 40 reviews

J.K.'s by the Bay

AliceRating, 5 stars1 week ago
We had a great weekend stay at Jeri and Dave’s home. It is a true vintage beach cottage, beautifully and comfortably decorated. It’s a short walk to both community beaches which were almost empty when we went. We enjoyed the huge deck and backyard fire pit. Jeri and Dave were very kind and helpful, proactive with recommendations, and even gave us some shark teeth for our son to “find” on the beach. It was a great weekend escape from Baltimore, and we’d absolutely return.

Destinations to explore