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Oakville Vacation Rentals

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Our top choices for Oakville vacation rentals

1. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 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 $286
CA $496 total
includes taxes & fees
Sep 8 - Sep 9
Bright and airy waterfront getaway

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $331
CA $811 total
includes taxes & fees
Sep 8 - Sep 9
Anne & Fred`s Leonardtown Home W/ Arcade room!

3. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is CA $599
CA $1,611 total
includes taxes & fees
Sep 8 - Sep 9
Lakefront Cabin Near Solomons Island w/ Hot Tub

4. 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
9.2 out of 10, Wonderful, (15 reviews)
"The owner was very nice "
United States
karen
The price is CA $212
CA $370 total
includes taxes & fees
Sep 8 - Sep 9
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

5. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $415
CA $1,003 total
includes taxes & fees
Sep 8 - Sep 9
4-BR Waterfront Turret Home

6. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (60 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $209
CA $430 total
includes taxes & fees
Oct 7 - Oct 8
Soul Oasis - home on the Chesapeake Bay

7. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $707
CA $1,583 total
includes taxes & fees
Sep 8 - Sep 9
Lakefront Cabin Near Solomons Island w/ Hot Tub

8. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $639
CA $1,175 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

9. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (55 reviews)
"My husband and I had a great 3 day getaway here. The view was spectacular! The convenience from walking to the dock to the house was awesome! The only “bad” thing I would say is the water….it has an awful sulfur smell that is very strong. Overall, we loved our stay & would stay here again!"
United States
Ashley D.
The price is CA $242
CA $471 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Virginia Potomac Riverfront Cottage

10. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $639
CA $1,372 total
includes taxes & fees
Sep 29 - Sep 30
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

11. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is CA $475
CA $1,104 total
includes taxes & fees
Sep 8 - Sep 9
Charming Waterfront 3-bedroom house in Piney Point

12. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is CA $217
CA $629 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (7 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $171
CA $363 total
includes taxes & fees
Sep 16 - Sep 17
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

14. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $477
CA $592 total
includes taxes & fees
Sep 8 - Sep 9
2 Bedroom Cottage at Coles Point Marina

15. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $191
CA $336 total
includes taxes & fees
Oct 5 - Oct 6
Coles Point Marina

16. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $377
CA $635 total
includes taxes & fees
Sep 9 - Sep 10
Plum Point Cottage #17

17. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
Lusby
The price is CA $274
CA $573 total
includes taxes & fees
Oct 7 - Oct 8
3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

18. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $199
CA $634 total
includes taxes & fees
Sep 8 - Sep 9
Family Beach House: Spacious Deck, Grill & Views
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?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This vacation home rental near Oakville offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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 St. Mary's River State Park. 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.