Oakville Holiday Rentals

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Our top choices for Oakville holiday rentals

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AU$529
includes taxes & fees
23 Feb - 24 Feb
Coles Point Marina

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is AU$741
includes taxes & fees
24 Feb - 25 Feb
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Back Creek Villa Open Deck Solomons Island Maryland

Back Creek Villa Open Deck Solomons Island Maryland
Solomons
The price is AU$365
includes taxes & fees
15 Mar - 16 Mar
Back Creek Villa Open Deck Solomons Island Maryland

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (41 reviews)
"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$412
includes taxes & fees
10 Mar - 11 Mar
Soul Oasis - home on the Chesapeake Bay

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is AU$832
includes taxes & fees
23 Feb - 24 Feb
Come relax yourself a while

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 AU$425
includes taxes & fees
23 Feb - 24 Feb
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AU$419
includes taxes & fees
23 Feb - 24 Feb
2 Bedroom Cottage at Coles Point Marina

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 AU$1,078
includes taxes & fees
23 Feb - 24 Feb
4-BR Waterfront Turret Home

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is AU$451
includes taxes & fees
23 Feb - 24 Feb
Cottage Located on the Patuxent River!

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is AU$521
includes taxes & fees
23 Feb - 24 Feb
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 AU$611
includes taxes & fees
18 Mar - 19 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (1 review)
"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 AU$813
includes taxes & fees
23 Feb - 24 Feb
Charming Waterfront 3-bedroom house in Piney Point

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, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is AU$571
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Prince Frederick
9.0 out of 10, Wonderful, (10 reviews)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
United States
Timothy H.
The price is AU$1,042
includes taxes & fees
16 Mar - 17 Mar
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

Cozy Beach Retreat with three bedrooms and three queen size beds...

Cozy Beach Retreat with three bedrooms and three queen size beds...
Saint Leonard
The price is AU$507
includes taxes & fees
1 Mar - 2 Mar
Cozy Beach Retreat with three bedrooms and three queen size beds...

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"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 AU$855
includes taxes & fees
10 Mar - 11 Mar
Anne & Fred`s Leonardtown Home W/ Arcade room!
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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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$412 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?

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! : This holiday home rental outside of Oakville is located on the beach, and has an outdoor pool, a fireplace 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 patio, a garden and an arcade/games room 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 Leonardtown Park. Jefferson Patterson Park and Museum and Battle Creek Cypress Swamp Sanctuary 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.