Oakville holiday rentals

We found 41 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of holiday rentals in Oakville that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a fireplace. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Oakville

Showing deals for:21 Nov - 28 Nov

Exceptional

(14 reviews)

Resort Style Country Living on the Patuxent River

St. Leonard, MD

9% off

AU$2,911 per night

includes taxes & fees

Sit on the patio and enjoy your coffee in the morning.

Exceptional

(24 reviews)

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby, MD

8% off

AU$981 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Oakville

Private, gated pier with amazing sunrise and sunset views!

Waterfront Cottage w/ Private Pier & Beach ~ Lil' Paradise On The Potomac

Sleeps 5 · 2 bedrooms · 1+ bathroom

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

Sleeps 3 · 1 bedroom · 1 bathroom

250 steps to beach & 4 blocks to boardwalk! Early/late in & out is standard!

Sleeps 6 · 3 bedrooms · 2 bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Book a holiday rental for your Oakville getaway

Learn about the unique charm of Oakville with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Oakville

Are you searching for top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Oakville a one-of-a-kind holiday spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Port of Leonardtown Winery (6.2 mi / 10 km)
Running Hare Vineyard (8.1 mi / 13.1 km)
Maryland International Raceway (10.2 mi / 16.4 km)
Perigeaux Vineyards and Winery (7.5 mi / 12.1 km)
Wicomico Shores Golf Course (11.2 mi / 18.1 km)
Breton Bay Golf Course (8.6 mi / 13.9 km)

Exploring the natural landscape of Oakville

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oakville is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

Battle Creek Cypress Swamp Sanctuary (7.4 mi / 11.9 km)
Barrett Island (9.1 mi / 14.6 km)
Matoaka Beach (10.4 mi / 16.7 km)
St. Mary's River State Park (10.4 mi / 16.7 km)
Flag Ponds Nature Park (10.5 mi / 16.9 km)
Annmarie Sculpture Garden and Arts Center (10.8 mi / 17.4 km)

Frequently asked questions

How much does it cost to rent a holiday home in Oakville?

Several things determine how much you pay for a holiday home in Oakville, including the time of year, property type and length of stay. But, all our holiday homes have one thing in common — amazing value. Just add your travel dates to find your home away from home.

How much does it cost to rent a beach house in Oakville?

The average price for a holiday home near the beach in Oakville depends on when you're travelling and the size and type of property you're searching for. Find prices easily and quickly on Stayz by entering your destination and travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.

What are the top attractions for families in Oakville?

Cape Saint Marys Marina will keep the kids busy during your Oakville escape. You'll find this family-friendly attraction within easy reach of the centre.

How old do you have to be to rent a holiday home in Oakville?

The minimum age allowed can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Oakville you want. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Oakville for?

It really depends on the Oakville property. To view all available options offering extended stays, just enter your travel dates and number of people into the Stayz search page. Enjoy having the whole property to yourself, along with home comforts like a kitchen, air conditioning and an outdoor space to run around in. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.