Oakville Holiday Rentals

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Our top choices for Oakville holiday rentals

9.8 out of 10, Exceptional, (40)
"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 NZ$469
includes taxes & fees
28 Jan - 29 Jan 2026
Soul Oasis - home on the Chesapeake Bay

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is NZ$547
includes taxes & fees
1 Jan - 2 Jan 2026
Cottage Located on the Patuxent River!
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
The price is NZ$515
includes taxes & fees
31 Dec - 1 Jan 2026
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.4 out of 10, Exceptional, (6)
"Great place to stay for a getaway "
United States
Adam W.
The price is NZ$304
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$744
includes taxes & fees
28 Jan - 29 Jan 2026
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.6 out of 10, Exceptional, (5)
"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 NZ$667
includes taxes & fees
4 Jan - 5 Jan 2026
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is NZ$703
includes taxes & fees
14 Jan - 15 Jan 2026
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
3.0 star property
The price is NZ$1,553
includes taxes & fees
30 Jan - 31 Jan 2026
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Holiday Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is NZ$661
includes taxes & fees
6 Jan - 7 Jan 2026
Potomac Vista Cottage

Holiday Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,293
includes taxes & fees
1 Jan - 2 Jan 2026
4-BR Waterfront Turret Home
2.0 star property
Peaceful tiny home Saltara where you can realx and unwind
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,505
includes taxes & fees
6 Jan - 7 Jan 2026
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is NZ$961
includes taxes & fees
31 Dec - 1 Jan 2026
Charming Waterfront 3-bedroom house in Piney Point
9.2 out of 10, Wonderful, (5)
"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 NZ$1,003
includes taxes & fees
7 Jan - 8 Jan 2026
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Mechanicsville

Come relax yourself a while
The price is NZ$1,011
includes taxes & fees
7 Jan - 8 Jan 2026
Come relax yourself a while
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 favorite 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 depends 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 NZ$469 per night. Entering your travel dates in the search wizard you might find 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?

Luxury estate with jacuzzi and private pier: This holiday home rental outside of Oakville is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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. Leonardtown Town Hall 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.