Chesapeake Ranch Estates-Drum Point Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chesapeake Ranch Estates-Drum Point vacation rentals

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

1. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $211
CA $422 total
includes taxes & fees
Nov 16 - Nov 17
Soul Oasis - home on the Chesapeake Bay
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

2. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is CA $497
CA $1,313 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

3. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is CA $612
CA $1,531 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront Cabin Near Solomons Island w/ Hot Tub
A pathway lined with trees and lights leading to a wooden building with a visible window.

4. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (16 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $653
CA $1,158 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

5. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $722
CA $1,617 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront Cabin Near Solomons Island w/ Hot Tub
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $216
CA $404 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A single-story house with a front porch, a small deck, and a number '4' on the side.

7. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
10.0 out of 10, Exceptional, (1 review)
"If you want a quiet slice of VA/Potomac waterfront, this is the place."
United States
John
The price is CA $217
CA $366 total
includes taxes & fees
Nov 10 - Nov 11
Coles Point Marina
A spacious living room with a large sofa, a television, and a view of the ocean.

8. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $424
CA $1,002 total
includes taxes & fees
Nov 10 - Nov 11
4-BR Waterfront Turret Home
A covered patio with a view of a lake, furnished with chairs and a table.

9. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $254
CA $509 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

10. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $228
CA $376 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

11. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $338
CA $790 total
includes taxes & fees
Nov 10 - Nov 11
Anne & Fred`s Leonardtown Home W/ Arcade room!
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

12. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is CA $276
CA $562 total
includes taxes & fees
Nov 20 - Nov 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A house with a large lawn and a dock extending into a calm lake.

13. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is CA $389
CA $448 total
includes taxes & fees
Nov 10 - Nov 11
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A house with a large lawn and a dock extending into a calm lake.

14. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is CA $350
CA $404 total
includes taxes & fees
Nov 10 - Nov 11
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A two-story house with a balcony, surrounded by trees and a wooden fence.

15. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (9 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is CA $370
CA $950 total
includes taxes & fees
Nov 10 - Nov 11
Charming Waterfront 3-bedroom house in Piney Point
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

16. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (56 reviews)
"My family and I had a great time at this property fishing and crabbing. We also did a day trip to Westmoreland State Park, where we got to hike to Fossils Beach."
United States
Carmelita A.
The price is CA $247
CA $460 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Virginia Potomac Riverfront Cottage
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

17. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is CA $312
CA $359 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront Getaway with Dock
Pool

18. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is CA $201
CA $567 total
includes taxes & fees
Dec 2 - Dec 3
Family Beach House: Spacious Deck, Grill & Views
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

19. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
The price is CA $551
CA $1,125 total
includes taxes & fees
Dec 1 - Dec 2
2 Acre Oasis with Private Beach! Family and dog friendly!
A lakeside view with chairs and a table, a rainbow, and trees.

20. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is CA $325
CA $517 total
includes taxes & fees
Nov 10 - Nov 11
Bright and airy waterfront getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Ranch Estates-Drum Point Hotel Reviews

A multi-story hotel with a covered entrance, large windows, and a prominent brand sign.
Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park
California

10/10 Excellent

It was great very clean and nice
Canada
Aaron
Reviewed November 10, 2025
Spark by Hilton California Lexington Park

Find out more about Chesapeake Ranch Estates-Drum Point

Everything you need to know about Chesapeake Ranch Estates-Drum Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Ranch Estates-Drum Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Ranch Estates-Drum Point vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake Ranch Estates-Drum Point vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake Ranch Estates-Drum Point. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Ranch Estates-Drum Point vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake Ranch Estates-Drum Point vacation rentals we have selected for you start as low as CA $210 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake Ranch Estates-Drum Point rentals

At Expedia, we put the best Chesapeake Ranch Estates-Drum Point vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesapeake Ranch Estates-Drum Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Ranch Estates-Drum Point vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Ranch Estates-Drum Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Chesapeake Ranch Estates-Drum Point?

Yes, we offer vacation rentals close to the most popular local attractions in Chesapeake Ranch Estates-Drum Point, or you can go with a more secluded option if you want a relaxing place to stay. Chesapeake Ranch Estates-Drum Point is known for its art.

What are some of the best vacation home rentals that Chesapeake Ranch Estates-Drum Point has to offer?

Belle of the Chesapeake Bay: This highly rated vacation home rental in Chesapeake Ranch Estates-Drum Point offers a patio, an arcade game room, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Chesapeake Ranch Estates-Drum Point is Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay.

How many vacation rentals will I find in Chesapeake Ranch Estates-Drum Point?

With 23 Expedia vacation rentals, you're sure to find just the right place for your Chesapeake Ranch Estates-Drum Point stay.

What can I see and do in Chesapeake Ranch Estates-Drum Point?

Chesapeake Bay and Drum Point Lake are a couple of lovely local spots to get outside and enjoy nature. Annmarie Sculpture Garden and Arts Center and Drum Point Lighthouse are a couple of places you'll find in the larger area.

What’s a vacation rental in Chesapeake Ranch Estates-Drum Point like?

A vacation rental is a private property you can stay in for a long or short time in Chesapeake Ranch Estates-Drum Point. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.