Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Oakville vacation rentals

Exterior
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (38)
"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 ￥19,468
￥43,748 total
includes taxes & fees
Dec 14 - Dec 15
Soul Oasis - home on the Chesapeake Bay
Outdoor dining
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Apartment in Port Republic

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
The price is ￥12,459
￥27,503 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Smart TV, books
4-BR Waterfront Turret Home

Vacation Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
United States
Rudy L.
The price is ￥46,722
￥105,480 total
includes taxes & fees
Dec 21 - Dec 22
4-BR Waterfront Turret Home
Sun loungers, beach towels
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Vacation Home in Montross

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (4)
"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.
The price is ￥26,563
￥63,807 total
includes taxes & fees
Dec 14 - Dec 15
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Smart TV, books
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Vacation Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5)
"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 ￥28,033
￥55,963 total
includes taxes & fees
Dec 17 - Dec 18
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Property grounds
Potomac Vista Cottage

Vacation Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is ￥20,246
￥56,998 total
includes taxes & fees
Dec 14 - Dec 15
Potomac Vista Cottage
Sun loungers
Cottage Located on the Patuxent River!

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"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.
The price is ￥41,349
￥49,443 total
includes taxes & fees
Dec 12 - Dec 13
Cottage Located on the Patuxent River!
Property grounds
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage in Benedict

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
The price is ￥28,033
￥45,451 total
includes taxes & fees
Dec 15 - Dec 16
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Vacation Home in Prince Frederick

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is ￥31,927
￥60,421 total
includes taxes & fees
Dec 14 - Dec 15
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Pool
Family Beach House: Spacious Deck, Grill & Views

Vacation Home in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ￥35,664
￥79,815 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Family Beach House: Spacious Deck, Grill & Views
TV, fireplace, video games, books
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Vacation Home in Lusby

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is ￥47,968
￥125,122 total
includes taxes & fees
Dec 16 - Dec 17
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Exterior
Charming Waterfront 3-bedroom house in Piney Point

Vacation Home in Piney Point

Charming Waterfront 3-bedroom house in 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 ￥46,722
￥89,261 total
includes taxes & fees
Dec 21 - Dec 22
Charming Waterfront 3-bedroom house in Piney Point
Fridge, microwave, oven, stovetop
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Leonardtown

Anne & Fred`s Leonardtown Home W/ Arcade room!
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 ￥38,935
￥88,392 total
includes taxes & fees
Dec 14 - Dec 15
Anne & Fred`s Leonardtown Home W/ Arcade room!
Interior
Peaceful tiny home Saltara where you can realx and unwind

Vacation Home in Lexington Park

Peaceful tiny home Saltara where you can realx and unwind
2.0 star property
The price is ￥22,302
￥28,057 total
includes taxes & fees
Dec 12 - Dec 13
Peaceful tiny home Saltara where you can realx and unwind
Dining
Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC

Cottage in Newburg

Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC
2.0 star property
The price is ￥28,228
￥71,313 total
includes taxes & fees
Dec 19 - Dec 20
Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC
Property grounds
Come relax yourself a while

Apartment in Mechanicsville

Come relax yourself a while
The price is ￥38,546
￥89,764 total
includes taxes & fees
Dec 12 - Dec 13
Come relax yourself a while
House (3 Bedrooms) | Interior
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Cottage in Lusby

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
The price is ￥66,501
￥140,957 total
includes taxes & fees
Dec 30 - Dec 31
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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

Extended Stay America Select Suites Lexington Park Pax River

Extended Stay America Select Suites Lexington Park Pax River

10/10 Excellent
"Clean room. Staff respect the room number privacy policy."
Derwin 1-night trip
Posted 3 days ago
Extended Stay America Select Suites Lexington Park Pax River

Find out more about Oakville

Search for holiday rentals in Oakville on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Oakville!

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?

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops: This vacation home rental near Oakville is located on the waterfront and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 6 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 Battle Creek Cypress Swamp Sanctuary. Greenwell State Park and Leonardtown Town Hall 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.