Oakville Holiday Rentals

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Holiday Rentals in Oakville

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons
9.6 out of 10, Exceptional, (7)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
The price is AU$863
includes taxes & fees
19 Nov - 20 Nov
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

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

Piney Point
10.0 out of 10, Exceptional, (13)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
United States
Dawn B.
Tiny, Funky, and Full of Love - Welcome to the Love Shack

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

Port Republic
10.0 out of 10, Exceptional, (180)
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and...
United States
Vicki K.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Nice little place to stay"
United States
Eric S.
The price is AU$430
includes taxes & fees
19 Nov - 20 Nov
Peaceful Waterfront Apartment in the Heart of Solomons Island

Shewell's A-Frame on Mill Creek

Lusby
10.0 out of 10, Exceptional, (6)
"Nice quiet area for a peaceful break from the hustle and bustle of daily living!"
United States
Nancy B.
Shewell's A-Frame on Mill Creek

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Tall Timbers
9.8 out of 10, Exceptional, (58)
"We had a wonderful experience and stay at this cute little cottage. Hosts were amazing as well. Cottage has everything you need. Cute decor, plenty of cookware, towels, linens, TV with streaming and comfortable couch. Communication with host was outstanding and easy check-in and check-out. Will definitely stay here again and strongly recommend to others as a place to stay in the area."
United States
Mary S.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
10.0 out of 10, Exceptional, (123)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (37)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is AU$434
includes taxes & fees
25 Nov - 26 Nov
Soul Oasis - home on the Chesapeake Bay

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

Newburg
9.8 out of 10, Exceptional, (154)
"Lovely place and location!"
United States
Christa W.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Discover tranquility near Calvert Cliffs

Saint Leonard
9.8 out of 10, Exceptional, (18)
"Comfortable beds, large house with awesome views…had a great experience"
United States
Deborah R.
Discover tranquility near Calvert Cliffs

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Lusby
9.6 out of 10, Exceptional, (5)
"So communicative and thoughtful- helpful throughout and it’s a wonderful house stocked with everything we’d want. Thank you!!"
United States
Elizabeth S.
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

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

Prince Frederick
9.4 out of 10, Exceptional, (3)
"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 AU$536
includes taxes & fees
25 Nov - 26 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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

Prince Frederick
10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is AU$531
includes taxes & fees
24 Nov - 25 Nov
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Cozy Virginia Potomac Riverfront Cottage

Hague
9.6 out of 10, Exceptional, (45)
"Wonderful views, clean home and quaint ! We highly recommend!"
United States
Tim R.
Cozy Virginia Potomac Riverfront Cottage

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

Lusby
10.0 out of 10, Exceptional, (62)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
United States
Whitney H.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Belle of the Chesapeake Bay

Lusby
9.0 out of 10, Wonderful, (18)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
United States
Christopher H.
Belle of the Chesapeake Bay

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

Lusby
10.0 out of 10, Exceptional, (53)
"Incredible property and stay."
United States
Hunter B.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby
10.0 out of 10, Exceptional, (26)
"Great place. Would definitely stay here again. "
United States
Joshua M.
Stunning Water Front Home with Private Dock and Beach and Sunsets

Privacy and space with world class views

Montross
9.8 out of 10, Exceptional, (89)
"A group of us stayed over a long weekend and had an amazing time on the property. This was an excellent spot to host friends for the weekend. "
United States
Stu D.
Privacy and space with world class views

Beach Club: your own private "Caribbean" resort

Piney Point
10.0 out of 10, Exceptional, (12)
"Beautiful home with lots of room for all 11 of us to enjoy meals and hanging out. Great space to accommodate all ages from 4 to 80. Hosts were very responsive and made us feel welcome. The pavilion at the beach was awesome and we spent alot of time there. Great stay , great memories and all had a memorable time. "
United States
Jen B.
Beach Club: your own private "Caribbean" resort
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

Find out more about Oakville

Everything you need to know about Oakville 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 Oakville 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 Oakville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oakville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakville. 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 Oakville 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 Oakville holiday rentals we have selected for you start as low as AU$430 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville 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 Oakville 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 Oakville 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 Oakville. 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 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?

Belle of the Chesapeake Bay: This holiday home rental outside of Oakville offers a patio, an arcade/games 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 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. Greenwell State Park and Jefferson Patterson Park and Museum 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.