House vacation rentals in Chesapeake Ranch Estates-Drum Point

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Popular amenities for Chesapeake Ranch Estates-Drum Point house rentals

House rentals with a pool

Guest favorite
Home in Montross
4.98 out of 5 average rating, 107 reviews

Waterfront | Kayaks+Beach+Pool | Gameroom+Firepit

BrittanyRating, 5 stars2 weeks ago
Connie’s place was great! Looked just like the photos. The house was clean and in a great area. Nice and friendly neighbors. We enjoyed the community beaches that are super close, clean and dog friendly. It was a prefect weekend trip. We would book here again!
Superhost
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars4 weeks ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Superhost
Home in Montross
4.92 out of 5 average rating, 208 reviews

The Glebe

KristinaRating, 5 stars3 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 favorite
Home in Cambridge
4.97 out of 5 average rating, 116 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars3 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 favorite
Home in Lusby
5 out of 5 average rating, 19 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

AlanRating, 5 stars5 days ago
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!
Guest favorite
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.
Guest favorite
Home in Montross
4.99 out of 5 average rating, 156 reviews

Beach Please! River cottage w/private beach & dock

LisaRating, 5 stars2 weeks ago
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.
Guest favorite
Home in Fort Washington
4.92 out of 5 average rating, 156 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

TheresaRating, 5 stars1 week ago
Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel

Weekly house rentals

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

Spacious Lakefront Cottage w/ Private Pier

PaulRating, 5 stars2 weeks 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!
Superhost
Home in Lusby
4.79 out of 5 average rating, 24 reviews

Belle of the Chesapeake Bay

KennethRating, 5 stars1 day ago
We had family and friends come from out of state just as well as we did, and it was a great weekend for everyone! We all enjoyed the house, as we all had our own rooms and were able to share time with each other and enjoy the family time! Great house!
Guest favorite
Home in Solomons
4.96 out of 5 average rating, 28 reviews

Solomons Yellow House - Waterfront

BeckyRating, 5 stars2 weeks ago
Came to Solomon’s for a wedding . Had a wonderful stay at John’s Place. All the comforts of home. Very clean, Fantastic location- easy walk to restaurant’s, shops, And Mass on Sunday ! Beautful water front property. Lovely decor- excellent kitchen space. Lovely the unique lighting, screened -in porch, and front porch! Very Comfy beds. Would def stay here again!!
Guest favorite
Home in Lusby
4.99 out of 5 average rating, 89 reviews

Waterfront with sweeping bay view & private beach

RahinRating, 5 stars4 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 favorite
Home in Solomons
4.99 out of 5 average rating, 78 reviews

Solomons home with harbor view!

GingerRating, 5 stars2 weeks 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.
Top guest favorite
Home in Solomons
5 out of 5 average rating, 27 reviews

4-BR Unique Waterfront House - Your Perfect Escape

SueRating, 5 stars2 weeks 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 favorite
Home in Saint Leonard
5 out of 5 average rating, 6 reviews

Waterfront Home, Spectacular View & Private Beach!

MargaretRating, 5 stars4 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.
Guest favorite
Home in Saint Leonard
4.94 out of 5 average rating, 71 reviews

Cottage on the Bay

HarrietRating, 5 stars1 week ago
We had a lovely stay at Jennifer’s cottage. Was great to get out of the city and be in such a peaceful area. Loved the private beaches and how quiet they were and easy to get to (on is literally at the end of the road). The kitchen was well equipped as described and Jennifer was easy to get in touch with. Really enjoyed and would love to come back again.

Private house rentals

Top guest favorite
Home in Hollywood
4.99 out of 5 average rating, 80 reviews

Waterfront Home: Osprey Getaway

DamarisRating, 5 stars1 week 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 favorite
Home in Coltons Point
4.95 out of 5 average rating, 20 reviews

The Eventide at Serenity Lane

AlexisRating, 5 stars3 weeks ago
Absolutely lovely! The home was so cute and such a peaceful location. All instructions were so clear and helpful! Truly a wonderful time.
Top guest favorite
Home in Lexington Park
5 out of 5 average rating, 10 reviews

Stunning Views, Remodeled Family-Friendly Home

TammiRating, 5 stars4 days ago
This was a truly lovely and clean home. Staying there was so wonderful - sitting on the screened porch listening to the water, walking the waterfront, lovely. It was so peaceful and calming of a location. Also, walking or biking distance to the St. Marys college and historical park. I recommend anyone stay there - I would again. We felt so comfortable and welcomed into this gorgeous waterfront property. You cannot beat the views and location. Communicative hosts. Thanks for a great stay!
Guest favorite
Home in Montross
4.91 out of 5 average rating, 22 reviews

Potomac River Getaway

SkyRating, 5 stars2 weeks 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!
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 Piney Point
4.81 out of 5 average rating, 52 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!
Superhost
Home in Port Republic
4.78 out of 5 average rating, 23 reviews

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

TakishaRating, 5 stars3 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!!
Top guest favorite
Home in Prince Frederick
5 out of 5 average rating, 16 reviews

Downs By The River

JeffRating, 5 stars2 weeks ago
We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!

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