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
4.99 out of 5 average rating, 105 reviews

Waterfront Retreat Beach+Pool | Gamerm | Dog+EV OK

DavidRating, 5 stars1 week ago
What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!
Superhost
Home in Montross
4.92 out of 5 average rating, 207 reviews

The Glebe

KateRating, 5 stars1 month ago
A great stay on the river. The kitchen was well equipped and the rest of the house was comfortable. The screened in porch and access to the dock/beach/river was our favorite part. Our dogs were in HEAVEN. The location is rather remote, so recommend bringing any food you'll want as there are no close stores or restaurants.
Guest favorite
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars1 week 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, 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 favorite
Home in Lusby
4.93 out of 5 average rating, 80 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, 155 reviews

Beach Please! River cottage w/private beach & dock

SarahRating, 5 stars1 week ago
My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!
Superhost
Home in Port Republic
4.78 out of 5 average rating, 23 reviews

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

TakishaRating, 5 stars1 week 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 favorite
Home in Fort Washington
4.92 out of 5 average rating, 155 reviews

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

SantiRating, 5 stars2 weeks ago
This place is fantastic for a stay. Daniel is super communicative and quick to respond. Plus, the pool is impeccably clean.

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

Waterfront Home: Osprey Getaway

DamarisRating, 5 starstoday
⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ 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 Cambridge
4.87 out of 5 average rating, 62 reviews

High St. Art Gallery Suite

NadineRating, 5 stars1 month ago
My husband and I had a nice peaceful retreat from city life. Kristin’s cute place was just what we needed. Highly recommend!
Guest favorite
Home in Taylors Island
5 out of 5 average rating, 15 reviews

Holliday House

JamesRating, 5 stars2 weeks ago
nice quiet place to relax and feel right at home
Guest favorite
Home in Lusby
4.99 out of 5 average rating, 88 reviews

Waterfront with sweeping bay view & private beach

MicheleRating, 5 stars3 weeks ago
The location is peaceful, private and gorgeous. It is as just what I wanted and needed for my 50th girls getaway! We loved every second there! The beds were comfy, location was quiet, the water and outdoor amenities were perfect! We easily made it work for 6 girls and one bathroom- which was no issue at all! A storm came through and left us a beautiful double rainbow! There is a resident bunny who comes out mornings to forage. We spent most of our time relaxing by the water with the chairs, loungers and umbrellas! My daughter and her friend played safely and happily on the shore by the water and my friend and I kayaked over by the cliffs. It was a perfect weekend at Colin’s and we plan to come back again! What fun and relaxation we had in a private setting with very nice neighbors. It went BEYOND our expectations! Colin was always kind and super timely when responding to any needs. We will be back! 💓🙌🏼
Top guest favorite
Home in Solomons
4.99 out of 5 average rating, 78 reviews

Solomons home with harbor view!

GingerRating, 5 stars6 days 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 stars3 weeks ago
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!
Top guest favorite
Home in Solomons
5 out of 5 average rating, 26 reviews

4-BR Unique Waterfront House - Your Perfect Escape

SueRating, 5 stars5 days 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!

Private house rentals

Superhost
Home in Lusby
4.86 out of 5 average rating, 50 reviews

Spacious Lakefront Cottage w/ Private Pier

PaulRating, 5 stars4 days 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 favorite
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 favorite
Home in Montross
4.9 out of 5 average rating, 21 reviews

Potomac River Getaway

SkyRating, 5 stars5 days 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 favorite
Home in Coltons Point
4.95 out of 5 average rating, 19 reviews

The Eventide at Serenity Lane

JulieRating, 5 stars2 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!
Top guest favorite
Home in Madison
5 out of 5 average rating, 27 reviews

Madison Bay Club House

JesseRating, 5 stars2 weeks ago
This place is amazing. We loved it and will be coming back soon. Jo was amazing and very responsive. Jo answered all text with questions we had and made our trip amazing. I recommend anyone looking for a peaceful water front getaway choose this house you won’t regret it. Very amazing place and host.
Top guest favorite
Home in Fishing Creek
5 out of 5 average rating, 47 reviews

Fishing Creek waterfront cottage

SophieRating, 5 stars3 weeks ago
Words cannot express how beautiful and picturesque Robin’s home and property is. I got married on Hoopers Island and we stayed at Robin’s home. The house itself is incredible, from the decorations, to the appliances, to the views; everything was phenomenal! I highly encourage anyone looking for a place to stay on Fishing Creek, to stay at Robins. Robin as a host was incredible. Responsive, generous and so kind. Thank you Robin for making my wedding weekend truly special!
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!
Guest favorite
Home in Saint Leonard
4.94 out of 5 average rating, 69 reviews

Cottage on the Bay

JaneRating, 5 stars1 week ago
Our third year of staying at Jennifer’s cottage and studio. A lovely location for a beach weekend with our family and grandchildren. The accommodation is comfortable and well equipped, the cottage having a full kitchen and large sunny deck with BBQ. The studio is cozy and perfect for a couple. The community beach is a 2 minute walk, quiet and safe for young swimmers. We didn’t get to enjoy the hot tub or use the kayaks ( too busy with little kids!) but maybe next year!

Destinations to explore