
House vacation rentals in Chesapeake Ranch Estates-Drum Point
Find and book unique houses on Airbnb
Top-rated house rentals in Chesapeake Ranch Estates-Drum Point
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Ranch Estates-Drum Point house rentals
House rentals with a pool

Waterfront | Kayaks+Beach+Pool | Gameroom+Firepit
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!

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

The Glebe
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!

Gorgeous, waterfront home - Perfect for Families.
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.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
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!

Spacious and private waterfront, sleeps 10
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.

Beach Please! River cottage w/private beach & dock
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.

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

Spacious Lakefront Cottage w/ Private Pier
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!

Belle of the Chesapeake Bay
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!

Solomons Yellow House - Waterfront
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!!

Waterfront with sweeping bay view & private beach
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!

Solomons home with harbor view!
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.

4-BR Unique Waterfront House - Your Perfect Escape
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!

Waterfront Home, Spectacular View & Private Beach!
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.

Cottage on the Bay
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

Waterfront Home: Osprey Getaway
⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ 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.

The Eventide at Serenity Lane
Absolutely lovely! The home was so cute and such a peaceful location. All instructions were so clear and helpful! Truly a wonderful time.

Stunning Views, Remodeled Family-Friendly Home
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!

Potomac River Getaway
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!

Abells Wharf Cottage - Natural Splendor Getaway
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!

2 Bedroom Cozy Beach Cottage
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!

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

Downs By The River
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!
Destinations to explore
- Washington Vacation rentals
- South Jersey Vacation rentals
- Philadelphia Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- Outer Banks Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- Hudson Valley Vacation rentals
- The Hamptons Vacation rentals
- Rentals with a patio Chesapeake Ranch Estates-Drum Point
- Pet-friendly rentals Chesapeake Ranch Estates-Drum Point
- Kid-friendly rentals Chesapeake Ranch Estates-Drum Point
- Rentals with a fire pit Chesapeake Ranch Estates-Drum Point
- Rentals with a fireplace Chesapeake Ranch Estates-Drum Point
- Rentals with a washer and dryer Chesapeake Ranch Estates-Drum Point
- Waterfront rentals Chesapeake Ranch Estates-Drum Point
- Rentals with beach access Chesapeake Ranch Estates-Drum Point
- Rentals with outdoor seating Chesapeake Ranch Estates-Drum Point
- Rentals with a kayak Chesapeake Ranch Estates-Drum Point
- Rentals with lake access Chesapeake Ranch Estates-Drum Point
- House rentals Calvert County
- House rentals Maryland
- House rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Nationals Park
- District Wharf
- Sandy Point State Park
- National Air and Space Museum
- National Harbor
- Lincoln Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Library of Congress
- Gerry Boyle Park
- Ragged Point Beach
- Leesylvania State Park
- Six Flags America
- Breezy Point Beach & Campground
- International Spy Museum
- Chesapeake Beach Water Park
- Idlewilde Restoration Project
- Sandyland Beach
- United States Botanic Garden
- Bayfront Beach
- Brownies Beach
- Rose Haven Memorial Park
- Quiet Waters Dog Beach
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes