Chesapeake Ranch Estates-Drum Point Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is AU$406
includes taxes & fees
30 Apr - 1 May
Soul Oasis - home on the Chesapeake Bay

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, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AU$1,379
includes taxes & fees
6 May - 7 May
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is AU$373
includes taxes & fees
29 Apr - 30 Apr
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is AU$606
includes taxes & fees
29 Apr - 30 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$609
includes taxes & fees
27 May - 28 May
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is AU$488
includes taxes & fees
29 Apr - 30 Apr
Cottage Located on the Patuxent River!

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AU$490
includes taxes & fees
29 Apr - 30 Apr
Coles Point Marina

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 AU$451
includes taxes & fees
30 Apr - 1 May
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is AU$723
includes taxes & fees
29 Apr - 30 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (13 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is AU$619
includes taxes & fees
3 May - 4 May
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is AU$781
includes taxes & fees
4 May - 5 May
Anne & Fred`s Leonardtown Home W/ Arcade room!

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$743
includes taxes & fees
29 Apr - 30 Apr
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (8 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is AU$538
includes taxes & fees
12 May - 13 May
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is AU$608
includes taxes & fees
13 May - 14 May
Sunset Breezes - quiet waterfront retreat

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (55 reviews)
"Great place, will stay again"
United States
Matt S.
The price is AU$389
includes taxes & fees
27 May - 28 May
Waterfront Getaway with Dock

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is AU$653
includes taxes & fees
5 May - 6 May
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is AU$605
includes taxes & fees
29 Apr - 30 Apr
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is AU$854
includes taxes & fees
3 May - 4 May
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (19 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is AU$496
includes taxes & fees
29 Apr - 30 Apr
Bright and airy waterfront getaway

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
4-BR Waterfront Turret Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Ranch Estates-Drum Point Hotel Reviews

Find out more about Chesapeake Ranch Estates-Drum Point

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

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Ranch Estates-Drum Point holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake Ranch Estates-Drum Point holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Ranch Estates-Drum Point holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake Ranch Estates-Drum Point holiday rentals we have selected for you start as low as AU$373 per night. Entering your travel dates in the search wizard might find you 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 holiday 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 holiday.

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 holiday rental in Chesapeake Ranch Estates-Drum Point?

Yes, there are holiday rentals close to the most popular sights in Chesapeake Ranch Estates-Drum Point, or you can select a more secluded option if you're looking for a relaxing stay. Chesapeake Ranch Estates-Drum Point is known for its art.

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

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR: This highly rated holiday home rental in Chesapeake Ranch Estates-Drum Point offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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

With 26 Expedia holiday rentals, you're guaranteed 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. Harbor Island Marina and Drum Point Lighthouse are a couple of places you'll find in the wider area.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake Ranch Estates-Drum Point. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family getaway.