Chesapeake Ranch Estates-Drum Point Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

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

House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is ￥37,963
￥110,616 total
includes taxes & fees
Apr 20 - Apr 21
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (44 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 ￥20,014
￥45,123 total
includes taxes & fees
Apr 22 - Apr 23
Soul Oasis - home on the Chesapeake Bay
TV, fireplace, video games, books

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 ￥76,879
￥159,441 total
includes taxes & fees
Apr 21 - Apr 22
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is ￥37,863
￥69,388 total
includes taxes & fees
Apr 21 - Apr 22
Coles Point Marina
Sun loungers

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 ￥46,461
￥55,647 total
includes taxes & fees
Apr 16 - Apr 17
Cottage Located on the Patuxent River!
Smart TV

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 ￥44,974
￥87,745 total
includes taxes & fees
Apr 20 - Apr 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, books

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 ￥33,356
￥68,358 total
includes taxes & fees
Apr 20 - Apr 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Property grounds

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 ￥24,303
￥42,269 total
includes taxes & fees
Apr 16 - Apr 17
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Dining

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, (12 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is ￥37,327
￥71,217 total
includes taxes & fees
Apr 21 - Apr 22
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior

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 ￥42,887
￥52,027 total
includes taxes & fees
Apr 16 - Apr 17
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is ￥48,608
￥93,786 total
includes taxes & fees
Apr 20 - Apr 21
Charming Waterfront 3-bedroom house in Piney Point
View from property

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 ￥39,710
￥85,035 total
includes taxes & fees
May 3 - May 4
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Smart TV, books

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.
The price is ￥55,594
￥123,665 total
includes taxes & fees
Apr 19 - Apr 20
4-BR Waterfront Turret Home
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is ￥54,800
￥67,228 total
includes taxes & fees
Apr 20 - Apr 21
2 Bedroom Cottage at Coles Point Marina
Beach

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 ￥43,204
￥80,144 total
includes taxes & fees
Apr 20 - Apr 21
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Interior

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, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is ￥29,385
￥62,208 total
includes taxes & fees
Apr 21 - Apr 22
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Pool

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 ￥27,003
￥69,655 total
includes taxes & fees
Apr 20 - Apr 21
Family Beach House: Spacious Deck, Grill & Views
Sun loungers, beach towels

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 ￥27,918
￥76,691 total
includes taxes & fees
Apr 19 - Apr 20
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Exterior

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 ￥42,887
￥52,027 total
includes taxes & fees
Apr 18 - Apr 19
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Outdoor dining

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 ￥54,345
￥67,756 total
includes taxes & fees
May 6 - May 7
Sunset Breezes - quiet waterfront retreat
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

Island Inn & Suites, an Ascend Collection Hotel

Island Inn & Suites, an Ascend Collection Hotel

6/10 Okay
"The lead-up to this one night stay was THE most stressful hotels dot com experience of my entire life. I paid for the room in December 2025, and between December 2025 and April 2026, I called Hotels.com for help to reschedule since I made a mistake and scheduled it during a time when one of my children was still in school and the other was on spring break. Numerous hours spent on phone calls, chats and emails were in vain as they claimed they couldn’t reach the property. I could not reach the property either, but since it is 2026, a landline phone should not have been their only option. I was forced to take my child out of school for two days. Even calling Choice Hotels, the parent company, didn’t help. When we finally got to the hotel, I asked why they didn’t answer their phones - ever - and they claimed their phone system was down and it would be back up shortly. How could a phone system be down for three months? They gave me an email address for future reference. Why didn’t Hotels.com have this? The stay itself was OK. We were just there for the sunrise, and nothing else. We had the free continental breakfast ( no eggs ) and coffee, and the staff apologized to us for the inconvenience. My husband told me that being on the balcony, watching the sun come up was his “happy place” on two different occasions, so I guess it was worth it. "
Adriann 1-night trip
Posted 17 hours ago
Island Inn & Suites, an Ascend Collection Hotel

Find out more about Chesapeake Ranch Estates-Drum Point

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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?

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR: This highly rated vacation home rental in Chesapeake Ranch Estates-Drum Point offers a fireplace, a patio, and a barbecue grill 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. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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

With 25 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. Calvert Marina and Harbor Island Marina 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.