Oakville Holiday Rentals

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Holiday Rentals in Oakville

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (37)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is NZ$471
includes taxes & fees
27 Nov - 28 Nov
Soul Oasis - home on the Chesapeake Bay

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict
9.0 out of 10, Wonderful, (6)
"Sophia the host is super attentive and responsive"
United States
Mayela
The price is NZ$529
includes taxes & fees
14 Nov - 15 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage Located on the Patuxent River!

Prince Frederick
10.0 out of 10, Exceptional, (42)
"Nice and quiet beautiful cottage. A+ communication and a gem. 10/10 will stay again."
United States
chris W.
The price is NZ$561
includes taxes & fees
14 Nov - 15 Nov
Cottage Located on the Patuxent River!

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick
9.4 out of 10, Exceptional, (3)
"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 NZ$693
includes taxes & fees
16 Nov - 17 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
The price is NZ$762
includes taxes & fees
14 Dec - 15 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Montross
10.0 out of 10, Exceptional, (4)
"They thought of everything. I would definitely come back for another stay."
United States
Donna D.
The price is NZ$739
includes taxes & fees
16 Nov - 17 Nov
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Port Republic
9.4 out of 10, Exceptional, (6)
"Great place to stay. Quiet comfortable neighborhood, plenty to do around if you’re outdoorsy. The location was comfortable & well stocked with anything you’d need. Would return. "
United States
Caleb R.
The price is NZ$312
includes taxes & fees
14 Nov - 15 Nov
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

3.0 star property
Lusby
The price is NZ$1,283
includes taxes & fees
14 Nov - 15 Nov
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
The price is NZ$487
includes taxes & fees
14 Nov - 15 Nov
Peaceful Waterfront Apartment in the Heart of Solomons Island

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick
10.0 out of 10, Exceptional, (8)
"This house was extremely clean and a comfortable choice for 4 older adults attending a family wedding in St Leonard. "
United States
Susan W.
The price is NZ$723
includes taxes & fees
17 Nov - 18 Nov
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

Prince Frederick
9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
United States
Timothy H.
The price is NZ$1,030
includes taxes & fees
14 Nov - 15 Nov
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

4-BR Waterfront Turret Home

2.0 star property
Solomons
10.0 out of 10, Exceptional, (7)
"A truly incredible property. Home is beyond beautiful, interesting design, terrific location where the river meets the bay. Saw dolphins jumping. Easy walk to downtown and restaurants. Turret style home is fascinating. Host incredibly accessible. Rent with confidence."
United States
Laura
The price is NZ$1,304
includes taxes & fees
1 Dec - 2 Dec
4-BR Waterfront Turret Home

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons
9.6 out of 10, Exceptional, (7)
"The house was beautiful and well stocked with the necessities and even extras we didn’t expect. The service from the owner was great and always quick to respond to our questions. We are definitely looking forward to staying at this or another property next year! "
United States
Shewana S.
The price is NZ$958
includes taxes & fees
17 Nov - 18 Nov
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Charming Waterfront 3-bedroom house in Piney Point

Piney Point
10.0 out of 10, Exceptional, (1)
"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 NZ$1,012
includes taxes & fees
16 Nov - 17 Nov
Charming Waterfront 3-bedroom house in Piney Point

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

Leonardtown
9.2 out of 10, Wonderful, (5)
"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 NZ$1,053
includes taxes & fees
14 Dec - 15 Dec
Anne & Fred`s Leonardtown Home W/ Arcade room!

Come relax yourself a while

Mechanicsville
The price is NZ$1,037
includes taxes & fees
14 Nov - 15 Nov
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

Everything you need to know about Oakville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakville holiday rentals we have selected for you start as low as NZ$487 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville holiday 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 holiday.

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 holiday rentals in Oakville?

Yes, there are holiday rentals close to the most popular sights in Oakville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakville has to offer?

Belle of the Chesapeake Bay: This holiday home rental outside of Oakville offers a patio, an arcade/games room and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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. Greenwell State Park and Jefferson Patterson Park and Museum are a couple of places you'll find in the wider area.

What’s a holiday rental in Oakville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakville. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for small groups.