Oakville Vacation Rentals

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Our top choices for Oakville vacation rentals

10.0 out of 10, Exceptional, (41 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is CA $187
CA $407 total
includes taxes & fees
Mar 9 - Mar 10
Soul Oasis - home on the Chesapeake Bay
9.0 out of 10, Wonderful, (8 reviews)
"Very nice location. Everything as described. Responsive host."
United States
Michael L.
The price is CA $209
CA $367 total
includes taxes & fees
Mar 4 - Mar 5
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cabin in Hague

Coles Point Marina
2.0 star property
The price is CA $363
CA $511 total
includes taxes & fees
Mar 4 - Mar 5
Coles Point Marina

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is CA $363
CA $438 total
includes taxes & fees
Mar 4 - Mar 5
Cottage Located on the Patuxent River!

Vacation Home in Chesapeak beach

Family Beach House: Spacious Deck, Grill & Views
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 $232
CA $605 total
includes taxes & fees
Mar 18 - Mar 19
Family Beach House: Spacious Deck, Grill & Views
The price is CA $327
CA $405 total
includes taxes & fees
Mar 15 - Mar 16
2 Bedroom Cottage at Coles Point Marina
9.6 out of 10, Exceptional, (5 reviews)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is CA $293
CA $559 total
includes taxes & fees
Mar 30 - Mar 31
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (8 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 $335
CA $607 total
includes taxes & fees
Mar 16 - Mar 17
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Vacation Home in Solomons

4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $479
CA $1,078 total
includes taxes & fees
Mar 4 - Mar 5
4-BR Waterfront Turret Home
9.4 out of 10, Exceptional, (6 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.
The price is CA $307
CA $766 total
includes taxes & fees
Mar 10 - Mar 11
Anne & Fred`s Leonardtown Home W/ Arcade room!
The price is CA $246
CA $544 total
includes taxes & fees
Mar 5 - Mar 6
Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is CA $220
CA $637 total
includes taxes & fees
Mar 4 - Mar 5
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is CA $246
CA $584 total
includes taxes & fees
Mar 9 - Mar 10
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is CA $409
CA $783 total
includes taxes & fees
Apr 3 - Apr 4
Charming Waterfront 3-bedroom house in Piney Point
3.0 star property
The price is CA $375
CA $949 total
includes taxes & fees
Mar 5 - Mar 6
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $450
CA $1,146 total
includes taxes & fees
Mar 5 - Mar 6
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Apartment in Mechanicsville

Come relax yourself a while
The price is CA $338
CA $810 total
includes taxes & fees
Mar 6 - Mar 7
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?

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! : This vacation home rental near Oakville is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and an arcade game room so you can immerse yourself in your vacation.

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 Leonardtown Park. Jefferson Patterson Park and Museum and Battle Creek Cypress Swamp Sanctuary 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.