Oakville Vacation Rentals

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Our top choices for Oakville vacation rentals

The Napa Residences

The Napa Residences
5.0 star property
Napa
8.8 out of 10, Excellent, (32 reviews)
"Great stay! Would highly recommend!"
United States
Sophie
$395 nightly
The price is $454
May 12 - May 13
Total with taxes and fees
The Napa Residences

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
8.0 out of 10, Very Good, (1 review)
"Muy bonito diseño interior en ambos la recepción y el cuarto."
Mexico
Tara
$291 nightly
The price is $338
May 17 - May 18
Total with taxes and fees
Sonoma Stonehouse, Wine Country Vibes

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$237 nightly
The price is $267
May 14 - May 15
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (77 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
$463 nightly
The price is $512
May 12 - May 13
Total with taxes and fees
Glen Ellen Retreats Sunset Cottage

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (73 reviews)
"We stayed for a girls weekend for a napa get away. and we brought the dog and it was a great stay. And clean too. Easy for a home base. And it was affordable. Would stay again "
United States
Valerie C.
$371 nightly
The price is $392
May 12 - May 13
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"Yes, our little buddy was welcome!"
United States
Doug G.
$318 nightly
The price is $382
May 13 - May 14
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (39 reviews)
"Perfect little cottage within walking distance to everything in downtown Calistoga! Bed was so comfy and the fireplace made it feel extra cozy. We definitely want to stay here again!"
United States
Cameron D.
$269 nightly
The price is $326
Jun 11 - Jun 12
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (85 reviews)
"Great house in a perfect location. Short distance to Jack London State Park, various wineries, and walking distance to lovely restaurants near by. We enjoyed our long weekend and will definitely stay here again when we're up in the area!"
United States
sandra h.
$482 nightly
The price is $534
May 12 - May 13
Total with taxes and fees
Glen Ellen Retreats Hot Tub Cottage

RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,374 reviews)
"Very friendly staff!"
Canada
Holly
$129 nightly
The price is $148
May 18 - May 19
Total with taxes and fees
RiverPointe Napa Valley Resort

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
$306 nightly
The price is $367
May 12 - May 13
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga

Bright & Stylish Home Stay Minutes from Wineries

Bright & Stylish Home Stay Minutes from Wineries
Petaluma
10.0 out of 10, Exceptional, (2 reviews)
"Host was very responsive to messages."
United States
Kelly P.
$486 nightly
The price is $486
May 18 - May 19
Total with taxes and fees
Bright & Stylish Home Stay Minutes from Wineries

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
$238 nightly
The price is $269
May 13 - May 14
Total with taxes and fees
Charming King Cottage

Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown

Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown
Petaluma
9.8 out of 10, Exceptional, (110 reviews)
"This was hands-down, one of my favorite VRBO‘s!!!! 5 star service gorgeous property, incredible amenities. "
United States
Jessieca M.
$271 nightly
The price is $271
May 12 - May 13
Total with taxes and fees
Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown

Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (163 reviews)
"Absolutely loved our time at the Glen Ellen retreat. The home is so cozy and welcoming. "
United States
Amanda D.
$479 nightly
The price is $530
May 18 - May 19
Total with taxes and fees
Glen Ellen Retreats Coastal Cottage

Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (11 reviews)
$318 nightly
The price is $318
May 12 - May 13
Total with taxes and fees
Cozy Wine Country Guesthouse with Private Pool & Yard

Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa

Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa
Napa
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was extremely nice and complete with all you could need while in vacation with your family. Everything was very comfortable. Kitchen was complete for us to cook our dinners and breakfasts. Krista, our host, was always available with constant communication with us. Lovely place to stay to visit Napa. "
United States
Rene Arturo Chen
$443 nightly
The price is $484
May 12 - May 13
Total with taxes and fees
Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa

Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun

Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun
Southwest Santa Rosa
9.8 out of 10, Exceptional, (61 reviews)
"The house is beautiful and clean and very accommodating!"
United States
Marcie N.
$598 nightly
The price is $671
May 17 - May 18
Total with taxes and fees
Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun

Cottage at Main Street Farmhouse!

Cottage at Main Street Farmhouse!
McPherson
10.0 out of 10, Exceptional, (88 reviews)
"Excellent location and cozy!"
United States
Lori
$326 nightly
The price is $369
Jun 1 - Jun 2
Total with taxes and fees
Cottage at Main Street Farmhouse!

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
Santa Rosa
9.4 out of 10, Exceptional, (25 reviews)
"Excellent place to relax with my family!"
United States
Tatem D.
$483 nightly
The price is $534
May 12 - May 13
Total with taxes and fees
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
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 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 $148 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 a vacation rental in Oakville?

Yes, we have vacation rentals in Oakville close to Folie a Deux, or you can go with a more remote option if you're looking for extra privacy while you relax. Oakville is known for its wineries and restaurants. Make sure you have time to check out the local tours and mountain views during your trip.

What are some of the best vacation home rentals in Oakville?

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella: This vacation home rental outside of Oakville is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and a hot tub.

What can I see and do in Oakville?

Family-friendly attractions include Folie a Deux, whereas Napa River is a spot to enjoy the outdoors. Opus One Winery and Robert Mondavi Winery are other places to visit while you're in town.

What are vacation rentals like in Oakville?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Oakville. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips.