Oakville Vacation Rentals

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Our top choices for Oakville vacation rentals

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
$881 nightly
The price is $978
May 26 - May 27
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
$288 nightly
The price is $313
Jun 1 - Jun 2
Total with taxes and fees
Coles Point Marina

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

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.0 out of 10, Wonderful, (7 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
$444 nightly
The price is $471
May 26 - May 27
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
$341 nightly
The price is $361
May 22 - May 23
Total with taxes and fees
Cottage Located on the Patuxent River!

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
$332 nightly
The price is $352
May 27 - May 28
Total with taxes and fees
Bright and airy waterfront getaway

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.
$930 nightly
The price is $1,027
May 25 - May 26
Total with taxes and fees
4-BR Waterfront Turret Home

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$389 nightly
The price is $423
May 22 - May 23
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$997 nightly
The price is $1,004
May 26 - May 27
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
$273 nightly
The price is $289
Jun 2 - Jun 3
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay

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, (4 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
$488 nightly
The price is $539
May 26 - May 27
Total with taxes and fees
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"This was a fantastic property and location for our stay in Lusby. The home is designed with families in mind, and there was plenty for everyone to do. The house is beautiful and in a quiet, residential community. You can walk to the beach less than two blocks away, and we found dozens of sharks teeth there! Josh was so helpful with advice throughout. We would definitely come again."
United States
Mollie O.
$1,014 nightly
The price is $1,075
Jun 21 - Jun 22
Total with taxes and fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr

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, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
$450 nightly
The price is $477
May 26 - May 27
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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.
$238 nightly
The price is $263
May 27 - May 28
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (3 reviews)
"Loved it! Wish we had more time to spend in the lovely rental. "
United States
Hilary B.
$537 nightly
The price is $593
May 28 - May 29
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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.
$466 nightly
The price is $488
May 26 - May 27
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views

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)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
$500 nightly
The price is $529
May 31 - Jun 1
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!

Come relax yourself a while

Come relax yourself a while
Mechanicsville
$532 nightly
The price is $587
May 25 - May 26
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $263 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville vacation 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 vacation.

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 vacation rentals in Oakville?

Yes, we offer vacation rentals close to well known sights in Oakville, or you can choose a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Oakville?

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.: This vacation home rental near Oakville is located on a river and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

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 larger area.

What’s a vacation rental in Oakville like?

A vacation rental is a private property you can book for several days or longer in Oakville. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family gatherings.