Holiday Rentals in Oakville

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Holiday Rentals in Oakville

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (178)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (51)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Tiny, Funky, and Full of Love - Welcome to the Love Shack

10.0 out of 10, Exceptional, (4)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (144)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront Solomons Apartment

9.6 out of 10, Exceptional, (11)
"Very clean, awesome location and amazing hosts!! "
The price is €255
includes taxes & fees
6 Sept - 7 Sept
Waterfront Solomons Apartment

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

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is €261
includes taxes & fees
26 Aug - 27 Aug
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (168)
"Rented the house to celebrate a graduation from St Mary’s College. It was perfect. "
Waterfront Wildlife Retreat on the Patuxent River

Maryland Vacation Rental w/ Private Pool & Dock

9.4 out of 10, Exceptional, (13)
"My daughter and I enjoyed the place, especially the pool. She really loved the bunk-beds too. I asked for an early check in and that was granted which gave my daughter and I more time to explore the area and Calvert Cliffs. It did rain the entire time which dampened the exploring, and it was low 70s in August for swimming, but we made the most of it and had enjoyable memories."
Maryland Vacation Rental w/ Private Pool & Dock

New! Cozy River Cottage with great views of the water!

9.6 out of 10, Exceptional, (10)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (16)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway

Cozy Virginia Potomac Riverfront Cottage

9.6 out of 10, Exceptional, (42)
"Clean, comfortable, quiet, and what a beautiful spot on the river! Thank you 😊 "
Cozy Virginia Potomac Riverfront Cottage

2 Mi to Lighthouse: Waterfront Home w/ Dock!

8.6 out of 10, Excellent, (38)
"we stayed for work, plenty of things to do in the area. plenty of space in the house. everything was clean."
2 Mi to Lighthouse: Waterfront Home w/ Dock!

Walk to Beach: Elegant Escape in Lusby!

10.0 out of 10, Exceptional, (1)
"The property was very comfortable, convenient, well organized and beautifully prepared. "
Walk to Beach: Elegant Escape in Lusby!

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (12)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

Beach & River Retreat. Spectacular house with private sand beach and hot tub!

10.0 out of 10, Exceptional, (49)
"We had the best time! It is a gorgeous and spacious house, and the beach and dock were perfect. Frank was so kind and easy to work with and we would all love to stay here again- highly recommend!"
Beach & River Retreat. Spectacular house with private sand beach and hot tub!

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

10.0 out of 10, Exceptional, (16)
"Great place! "
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (29)
"We had an amazing stay in this beautiful house! Inside was massive perfectly set up for our needs. Outside had stunning views and there is nothing better than being on the waters edge. The owners were easy to communicate with and they had everything ready in a timely manner for our check in. We didn’t get a chance to catch any crabs but we will definitely stay here again to try our hand at that."
WATERFRONT!!! The River's Roost on The Patuxent River

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

10.0 out of 10, Exceptional, (1)
"This is a beautiful cottage in a quiet country setting. Our travel had us arriving a little early and Hannah graciously allowed us to check in early. Bathroom doors were attractive and trendy but did not lock or offer complete privacy. "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths

10.0 out of 10, Exceptional, (78)
"Gorgeous property to stay in and celebrate our daughter's graduation from St Mary's College of Maryland. A paradise so close to campus. "
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
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 Oakville Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Oakville?

Yes, there are holiday rentals close to the most popular sights in Oakville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakville has to offer?

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: This holiday home rental outside of Oakville is located on a lake, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Oakville?

While exploring the area, visit family-friendly sights like R&J's PlayPark, or get outside and enjoy nature at Battle Creek Cypress Swamp Sanctuary. Port of Leonardtown Winery and Leonardtown Town Hall are a couple of places you'll find in the wider area.

What’s a holiday rental in Oakville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakville. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for small groups.