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
The price is CA $587
CA $1,345 total
includes taxes & fees
May 26 - May 27
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $321
CA $476 total
includes taxes & fees
May 21 - May 22
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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is CA $316
CA $631 total
includes taxes & fees
May 21 - May 22
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.
The price is CA $414
CA $500 total
includes taxes & fees
May 25 - May 26
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.
The price is CA $284
CA $489 total
includes taxes & fees
May 31 - Jun 1
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.
The price is CA $756
CA $1,431 total
includes taxes & fees
May 25 - May 26
4-BR Waterfront Turret Home

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $474
CA $587 total
includes taxes & fees
May 28 - May 29
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.
The price is CA $665
CA $1,399 total
includes taxes & fees
May 21 - May 22
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.
The price is CA $190
CA $414 total
includes taxes & fees
May 26 - May 27
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.
The price is CA $357
CA $725 total
includes taxes & fees
May 21 - May 22
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.
The price is CA $448
CA $984 total
includes taxes & fees
Jun 2 - Jun 3
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.
The price is CA $337
CA $659 total
includes taxes & fees
May 26 - May 27
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.
The price is CA $210
CA $366 total
includes taxes & fees
May 31 - Jun 1
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.
The price is CA $423
CA $816 total
includes taxes & fees
Jun 1 - Jun 2
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.
The price is CA $234
CA $668 total
includes taxes & fees
May 26 - May 27
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.
The price is CA $278
CA $736 total
includes taxes & fees
Jun 1 - Jun 2
Anne & Fred`s Leonardtown Home W/ Arcade room!

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is CA $340
CA $814 total
includes taxes & fees
May 25 - May 26
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.