Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Oakville vacation rentals

Exterior

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (40 reviews)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$252 nightly
The price is $267
Jan 26 - Jan 27
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Cottage, 2 Bedrooms, Kitchen | Exterior

Cabin in Hague

Coles Point Marina
2.0 star property
$344 nightly
The price is $375
Jan 15 - Jan 16
Total with taxes and fees
Coles Point Marina
Property grounds

Cottage in Benedict

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.0 out of 10, Wonderful, (8 reviews)
"The owner was very nice "
United States
karen
$273 nightly
The price is $301
Jan 15 - Jan 16
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Marina

Vacation Home in Solomons

Back Creek Villa Open Deck Solomons Island Maryland
2.0 star property
$245 nightly
The price is $260
Jan 15 - Jan 16
Total with taxes and fees
Back Creek Villa Open Deck Solomons Island Maryland
Sun loungers

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
$303 nightly
The price is $321
Jan 15 - Jan 16
Total with taxes and fees
Cottage Located on the Patuxent River!
Property grounds

Vacation Home in Leonardtown

Potomac Vista Cottage
2.0 star property
$351 nightly
The price is $353
Jan 19 - Jan 20
Total with taxes and fees
Potomac Vista Cottage
Exterior

Cottage in Hague

2 Bedroom Cottage at Coles Point Marina
2.0 star property
$268 nightly
The price is $292
Jan 15 - Jan 16
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina
Sun loungers, beach towels

Vacation Home in Montross

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
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.
$374 nightly
The price is $407
Jan 25 - Jan 26
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
House (3 Bedrooms) | Interior

Cottage in Lusby

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
$754 nightly
The price is $837
Jan 15 - Jan 16
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Beach

Vacation Home in Prince Frederick

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (8 reviews)
"Everything was amazing. "
United States
Lorie S.
$385 nightly
The price is $408
Jan 15 - Jan 16
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Exterior

Vacation Home in Piney Point

Charming Waterfront 3-bedroom house in 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.
$519 nightly
The price is $573
Jan 15 - Jan 16
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
Smart TV, books

Vacation Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$677 nightly
The price is $748
Jan 21 - Jan 22
Total with taxes and fees
4-BR Waterfront Turret Home
TV, fireplace, video games, books

Vacation Home in Lusby

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$868 nightly
The price is $874
Jan 15 - Jan 16
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Fridge, microwave, oven, stovetop

Apartment in Leonardtown

Anne & Fred`s Leonardtown Home W/ Arcade room!
9.2 out of 10, Wonderful, (5 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.
$541 nightly
The price is $573
Jan 18 - Jan 19
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
Property grounds

Apartment in Mechanicsville

Come relax yourself a while
$536 nightly
The price is $591
Jan 15 - Jan 16
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

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"My stay was great! The staff was courteous and helpful, and the room was nice and clean."
Linda 1-night trip
Posted 3 days ago
Solomons Inn Resort & Marina

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 $267 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.

Explore a world of travel with Expedia

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?

Shewell's A-Frame on Mill Creek: This vacation home rental near Oakville offers a patio, a selection of games, 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 fridge, and a stovetop, 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 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.