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
The price is CA $35
CA $622 total
includes taxes & fees
May 11 - May 12
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
The price is CA $207
CA $438 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $159
CA $368 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $342
CA $705 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $260
CA $563 total
includes taxes & fees
May 12 - May 13
Wine Country Cottage in downtown Santa Rosa, CA

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.
The price is CA $359
CA $727 total
includes taxes & fees
May 10 - May 11
Glen Ellen Retreats Coastal Cottage

Charming Napa Retreat | Walk to Wineries & Dining

Charming Napa Retreat | Walk to Wineries & Dining
Napa County
8.4 out of 10, Very good, (21 reviews)
"Beautiful location. Some of the things listed as walking distance required a lot of walking."
United States
Debbi S.
The price is CA $151
CA $756 total
includes taxes & fees
Jun 1 - Jun 2
Charming Napa Retreat | Walk to Wineries & Dining

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.
The price is CA $376
CA $748 total
includes taxes & fees
May 10 - May 11
Glen Ellen Retreats Hot Tub Cottage

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
The price is CA $424
CA $751 total
includes taxes & fees
May 11 - May 12
Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa

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.
The price is CA $395
CA $537 total
includes taxes & fees
May 12 - May 13
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

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.
The price is CA $247
CA $377 total
includes taxes & fees
May 12 - May 13
Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is CA $286
CA $370 total
includes taxes & fees
May 13 - May 14
Charming King 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)
The price is CA $381
CA $436 total
includes taxes & fees
May 12 - May 13
Cozy Wine Country Guesthouse with Private Pool & Yard

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.
The price is CA $381
CA $523 total
includes taxes & fees
May 13 - May 14
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is CA $198
CA $561 total
includes taxes & fees
May 11 - May 12
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (73 reviews)
"Loved our stay!!"
United States
kristen s.
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is CA $245
CA $314 total
includes taxes & fees
May 18 - May 19
Comfort and Style in Our Queen Cottage

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.
The price is CA $304
CA $660 total
includes taxes & fees
May 11 - May 12
Bright & Stylish Home Stay Minutes from Wineries

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.
The price is CA $307
CA $734 total
includes taxes & fees
May 11 - May 12
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

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
The price is CA $287
CA $500 total
includes taxes & fees
Jun 1 - Jun 2
Cottage at Main Street Farmhouse!
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 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.