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Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Oakville vacation rentals

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

1. 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, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$260 nightly
The price is $287
Nov 2 - Nov 3
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Private kitchen

2. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
$209 nightly
The price is $230
Nov 2 - Nov 3
Total with taxes and fees
Just a getaway piece of property
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

3. 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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$269 nightly
The price is $285
Nov 2 - Nov 3
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A lakeside view with chairs and a table, a rainbow, and trees.

4. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
$361 nightly
The price is $383
Nov 2 - Nov 3
Total with taxes and fees
Bright and airy waterfront getaway
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

5. 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.
$548 nightly
The price is $581
Nov 1 - Nov 2
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
A single-story house with a front porch, a small deck, and a number '4' on the side.

6. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
10.0 out of 10, Exceptional, (1 review)
"If you want a quiet slice of VA/Potomac waterfront, this is the place."
United States
John
$255 nightly
The price is $278
Nov 2 - Nov 3
Total with taxes and fees
Coles Point Marina
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

7. 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
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
$292 nightly
The price is $309
Nov 2 - Nov 3
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A spacious living room with a large sofa, a television, and a view of the ocean.

8. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$665 nightly
The price is $734
Nov 1 - Nov 2
Total with taxes and fees
4-BR Waterfront Turret Home
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

9. 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.
$1,041 nightly
The price is $1,125
Nov 1 - Nov 2
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

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, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
$960 nightly
The price is $966
Nov 3 - Nov 4
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A pathway lined with trees and lights leading to a wooden building with a visible window.

11. 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, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
$803 nightly
The price is $851
Nov 2 - Nov 3
Total with taxes and fees
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

12. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (56 reviews)
"This is our 4th time to come here and the view still amaze me. Fishing is great in this area. My family and I really had an amazing, fun and relaxing stay as always. See you next time."
United States
Natt L.
$315 nightly
The price is $343
Oct 30 - Oct 31
Total with taxes and fees
Cozy Virginia Potomac Riverfront Cottage
A modern kitchen with stainless steel appliances, a central island, and a dining area with a view of the outdoors.

13. Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks

Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
$452 nightly
The price is $484
Nov 1 - Nov 2
Total with taxes and fees
Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

14. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
$768 nightly
The price is $848
Nov 2 - Nov 3
Total with taxes and fees
2 Acre Oasis with Private Beach! Family and dog friendly!
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

15. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
$1,031 nightly
The price is $1,144
Nov 1 - Nov 2
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
Fire pit (2)

16. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$429 nightly
The price is $474
Oct 30 - Oct 31
Total with taxes and fees
Plum Point Cottage #17
A two-story house with a balcony, surrounded by trees and a wooden fence.

17. 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
$693 nightly
The price is $765
Oct 30 - Oct 31
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
A single-story house with a front porch, a small deck, and a number '4' on the side.

18. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$389 nightly
The price is $423
Oct 30 - Oct 31
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina
Fire pit (2)

19. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
$507 nightly
The price is $560
Oct 30 - Oct 31
Total with taxes and fees
Plum Point Cottage #14
Fire pit (2)

20. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
$534 nightly
The price is $590
Oct 30 - Oct 31
Total with taxes and fees
Plum Point Cottage #15
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

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"Quiet clean, decent breakfast, plenty of parking"
Terri 1-night trip
Posted 4 hours ago
avid hotel California - Lexington Park by IHG

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 $278 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?

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 Three Notch Park. Jefferson Patterson Park and Museum and Running Hare Vineyard 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.