Waterfront holiday rentals in Chesapeake Ranch Estates-Drum Point

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Popular amenities for Chesapeake Ranch Estates-Drum Point waterfront rentals

Waterfront apartment accommodation

Top Guest favourite
Apartment in Solomons
5 out of 5 average rating, 31 reviews

Escape to Pax River!

MariaRating, 5 stars2 weeks ago
Location, both the island and apartment, is wonderful. View of the water. Close to restaurants. Our stay this May was peaceful. Host treated my spouse and I kindly. Super clean apartment. Advice: do the easy hike to Calvert Cliffs for fossils on beach. Visit the Annmarie sculpture garden and art center. It's a true gem.
Top Guest favourite
Apartment in California
4.98 out of 5 average rating, 86 reviews

Blue Heron on Little Kingston Creek

VasuhiRating, 5 stars1 month ago
This is a beautiful waterfront property located close to everything that Lexington Park had to offer. The host has organized the apartment very neatly with lots of useful information and entertainment. We enjoyed our stay and look forward to visiting again
Apartment in Piney Point
5 out of 5 average rating, 4 reviews

Cozy in Saint George Island

CynthiaRating, 5 stars1 week ago
We wanted peace and quiet and that’s what it offered. Our children sent me for my birthday. We arrived at night so it was hard to see the address that’s when we realized others were on the property. Very clean and fresh. A few more kitchen amenities would have been nice. A nice touch of a birthday balloon and treats. We would come back again. Thanks
Top Guest favourite
Apartment in Leonardtown
4.98 out of 5 average rating, 135 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

KyleRating, 5 stars1 month ago
What a calm and peaceful private retreat! My fiancée and I spent a couple of days enjoying the brisk bay breezes and beautiful sunsets at Vickie’s. Everything was exactly as advertised and Vickie (and Scott) are true treasures—extremely responsive and thoughtful hosts who want you to have everything you need. Plus, their knowledge of the area gave us a great introduction to Leonardtown. So much more to the area than we thought! Whether birdwatching from “the best view on the block” or reflecting on the glider by the bay, we loved every moment of quiet and can’t wait to visit again. Thank you!
Top Guest favourite
Apartment in Port Republic
4.97 out of 5 average rating, 205 reviews

Serenity Suite on Chesapeake Bay

KristaRating, 5 stars3 days ago
This is our second time staying at this cozy and tranquil retreat—and it won’t be our last. We first came here six months ago for a quiet getaway from the kids, and we liked it so much we knew we’d be back. This time was just as wonderful. The place is spotless, peaceful, and incredibly relaxing. The view of the bay is absolutely stunning—calm, quiet, and the perfect backdrop for unwinding. The hosts are warm and welcoming, and the space has everything you need for a comfortable and refreshing stay. If you’re looking for a serene escape with beautiful scenery and thoughtful touches, this is the place. We’re already planning our next visit.
Guest favourite
Apartment in Colonial Beach
5 out of 5 average rating, 31 reviews

Sandy Feet Retreat - Beachfront

ElizabethRating, 5 stars1 week ago
Brittany’s waterfront home in Colonial Beach was a beautiful and peaceful retreat for me, my husband, and our 2 year old son. The space is beautiful and clean and offers lovely views of the sparkling water and beach just steps from the front door. We loved having beach days and visiting the pool, and nearby restaurants made it easy to grab lunch and dinner after a busy day in the sun. The in-unit washer and dryer made it easy to clean our swimsuits and stay on top of laundry, and the fully stocked kitchen made cooking a breeze. The porch also provides a nice space to take in the views and the sounds of waves crashing in a private and peaceful retreat. We loved visiting Colonial Beach and would happily stay at Brittany’s home again!
Top Guest favourite
Apartment in Lexington Park
4.97 out of 5 average rating, 568 reviews

Historic St. Mary's City, MD

AnnaRating, 5 stars6 days ago
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.
Superhost
Apartment in Solomons
4.74 out of 5 average rating, 35 reviews

Waterfront Solomons Apartment

ElizabethRating, 5 stars2 weeks ago
We came in very late our 3 hour drive turned into 4 1/2 due to severe thunderstorms and heavy rain. It’s was our safe harbor. Solomans island is very beautiful. Unfortunately we misunderstood the check out time on top of we were waiting on a boat surveyor. The place was clean and close to many attractions and shops.

Waterfront house rentals

Guest favourite
Home in Hague
4.97 out of 5 average rating, 162 reviews

Osprey's roost: Spring and summer 2025

DavidRating, 5 stars1 day ago
Very roomy for a family vacation. Great location and covered porch was great for taking in views of river and enjoying summer breeze. Host was responsive and provided detailed instructions.
Guest favourite
Home in Lusby
4.89 out of 5 average rating, 64 reviews

Beachfront Oasis with Amazing Views

NguyetRating, 5 stars3 weeks ago
We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.
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.
Top Guest favourite
Home in TYLERTON
4.96 out of 5 average rating, 134 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

SusanRating, 5 stars2 weeks ago
Wonderful accommodations for a relaxing visit to a beautiful island!
Guest favourite
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 Scotland
4.9 out of 5 average rating, 132 reviews

Spacious Gorgeous Waterfront Home with Sunset View

AlisonRating, 5 stars1 week ago
This home is just as advertised...it is very large, great for several families vacationing together! Our group was small so we didn't even make use of all of the space. The house is right on Tanner Creek which is just beautiful for sitting on the dock and relaxing, paddleboarding and kayaking, birdwatching, etc. It's also about a mile from Lookout Point State Park which is absolutely gorgeous. Restaurants and grocery stores are few and far between in this area, so it's a good idea to bring your own food, and the kitchen is well stocked with pots and pans for cooking. If you are looking for a place to relax in a calm and beautiful setting, this is it!
Top Guest favourite
Home in Lusby
4.93 out of 5 average rating, 15 reviews

Riverview Retreat

Helena LightRating, 5 stars2 weeks ago
This served as a low key weekend retreat for us. We unplugged and enjoyed being in each other’s company. Being on the river, surrounded by trees and birdwatching was exactly what we needed. The kitchen was well appointed so we were able to enjoy family favorite activities (cooking together and playing board games).
Top Guest favourite
Home in Tracys Landing
4.99 out of 5 average rating, 212 reviews

The Little Gypsy BoHome

Jane AnnRating, 5 stars1 week ago
Wonderful place - pictures do not do it justice. Home is spotless and beautifully furnished! We had a great time relaxing on our babymoon. Lots of great restaurants close by and so much to do at the house you never have to leave. Really appreciated the details such as the coloring station and ample beach towels. Hope to stay again in the future!

Destinations to explore