Holiday Rentals in Chesapeake Ranch Estates-Drum Point

  • 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

10.0 out of 10, Exceptional, (41 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is €245
includes taxes & fees
15 Mar - 16 Mar
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €708
includes taxes & fees
3 Mar - 4 Mar
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
3.0 star property
The price is €589
includes taxes & fees
3 Mar - 4 Mar
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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 €224
includes taxes & fees
4 Mar - 5 Mar
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (11 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is €265
includes taxes & fees
3 Mar - 4 Mar
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is €269
includes taxes & fees
3 Mar - 4 Mar
Cottage Located on the Patuxent River!
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 €367
includes taxes & fees
18 Mar - 19 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Cabin in Hague

Coles Point Marina
2.0 star property
The price is €317
includes taxes & fees
3 Mar - 4 Mar
Coles Point Marina
The price is €249
includes taxes & fees
3 Mar - 4 Mar
2 Bedroom Cottage at Coles Point Marina
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is €304
includes taxes & fees
16 Mar - 17 Mar
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
9.6 out of 10, Exceptional, (5 reviews)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is €327
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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 €274
includes taxes & fees
3 Mar - 4 Mar
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
The price is €225
includes taxes & fees
15 Mar - 16 Mar
Back Creek Villa Open Deck Solomons Island Maryland
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is €375
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is €350
includes taxes & fees
3 Mar - 4 Mar
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is €386
includes taxes & fees
3 Mar - 4 Mar
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
9.4 out of 10, Exceptional, (6 reviews)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
The price is €465
includes taxes & fees
15 Mar - 16 Mar
Anne & Fred`s Leonardtown Home W/ Arcade room!

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is €233
includes taxes & fees
3 Mar - 4 Mar
Waterfront Getaway with Dock

Holiday Home in Solomons

4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €663
includes taxes & fees
3 Mar - 4 Mar
4-BR Waterfront Turret Home
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 €441
includes taxes & fees
3 Mar - 4 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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, apart-hotels, 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 favorite 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 depends 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 €245 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 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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of Chesapeake Ranch Estates-Drum Point is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

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

With 23 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?

Drum Point Lake and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Annmarie Sculpture Garden and Arts Center and Harbor Island Marina 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.