A vineyard with rows of grapevines, a wooden post with the number 7, and a mountain range in the background.

Oakville Vacation Rentals

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Our top choices for Oakville vacation rentals

1. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (41 reviews)
"Nice, great location."
United States
Juan
The price is CA $42
CA $647 total
includes taxes & fees
Sep 8 - Sep 9
The Napa Residences

2. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,477 reviews)
"The room was clean and the location was great."
United States
Cynthia
The price is CA $136
CA $204 total
includes taxes & fees
Sep 21 - Sep 22
RiverPointe Napa Valley Resort

3. King bedroom #1 Wine Country Gateway With BBQ+Billiards

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is CA $311
CA $393 total
includes taxes & fees
Sep 8 - Sep 9
King bedroom #1 Wine Country Gateway With BBQ+Billiards

4. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (171 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is CA $346
CA $717 total
includes taxes & fees
Sep 8 - Sep 9
Glen Ellen Retreats Coastal Cottage

5. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (81 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is CA $346
CA $717 total
includes taxes & fees
Sep 7 - Sep 8
Glen Ellen Retreats Sunset Cottage

6. Romantic Wine Country Retreat with Hot Tub

Romantic Wine Country Retreat with Hot Tub
Boyes Hot Springs
9.8 out of 10, Exceptional, (54 reviews)
"This is just what you need for a getaway to enjoy the sights and tastes of Sonoma and Napa. Our hosts were exceptional from start to finish and truly care about your experience at their quaint and spotless property. "
United States
Lisa G.
The price is CA $244
CA $465 total
includes taxes & fees
Sep 29 - Sep 30
Romantic Wine Country Retreat with Hot Tub

7. 2 bed I Silverado Resort & Spa in Napa - Wine Town

2 bed I Silverado Resort & Spa in Napa - Wine Town
Napa
10.0 out of 10, Exceptional, (16 reviews)
"We had a great weekend getaway! Great location to both downtown Napa and wineries. "
United States
Joy S.
The price is CA $230
CA $500 total
includes taxes & fees
Sep 9 - Sep 10
2 bed I Silverado Resort & Spa in Napa - Wine Town

8. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (94 reviews)
"The stay was very nice"
United States
ladonna A.
The price is CA $381
CA $760 total
includes taxes & fees
Sep 7 - Sep 8
Glen Ellen Retreats Hot Tub Cottage

9. Cozy Napa Escape Silverado Resort

Cozy Napa Escape Silverado Resort
Napa
9.4 out of 10, Exceptional, (13 reviews)
"Loved to stay at this property. It was a short Uber ride to lots of wineries and the resort was so beautiful. Super comfy and convenient. The parking was easy, super clean and the check in was so easy."
United States
Carla
The price is CA $172
CA $371 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Napa Escape Silverado Resort

10. 1 bed | 1 bath | Silverado Resort Experience

1 bed | 1 bath | Silverado Resort Experience
Napa
10.0 out of 10, Exceptional, (20 reviews)
"Great location on the property and close to all the sites Napa has to offer. "
United States
Patricia L.
The price is CA $247
CA $453 total
includes taxes & fees
Oct 4 - Oct 5
1 bed | 1 bath | Silverado Resort Experience

11. Napa relaxation at its finest at Silverado Resort

Napa relaxation at its finest at Silverado Resort
Napa
10.0 out of 10, Exceptional, (7 reviews)
"Place was great, wish we could’ve stayed longer. "
United States
Jennifer C.
The price is CA $196
CA $462 total
includes taxes & fees
Sep 8 - Sep 9
Napa relaxation at its finest at Silverado Resort

12. Cottage at Main Street Farmhouse!

Cottage at Main Street Farmhouse!
McPherson
10.0 out of 10, Exceptional, (96 reviews)
"Excellent location and cozy!"
United States
Lori
The price is CA $298
CA $514 total
includes taxes & fees
Sep 7 - Sep 8
Cottage at Main Street Farmhouse!

13. Luxe 1BR Condo Par Excellence at Silverado Resort

Luxe 1BR Condo Par Excellence at Silverado Resort
Napa
9.8 out of 10, Exceptional, (34 reviews)
"Great place to stay and host was on top of all communication !"
United States
Nina S.
Luxe 1BR Condo Par Excellence at Silverado Resort

14. Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools

Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools
Glen Ellen
The price is CA $415
CA $743 total
includes taxes & fees
Sep 7 - Sep 8
Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools

15. Luxe apartment close to wineries EZ walk downtown resturants and tasting rooms

Luxe apartment close to wineries EZ walk downtown resturants and tasting rooms
McPherson
10.0 out of 10, Exceptional, (96 reviews)
"Lovely place, host was wonderful."
United States
Matthew S.
The price is CA $305
CA $463 total
includes taxes & fees
Sep 7 - Sep 8
Luxe apartment close to wineries EZ walk downtown resturants and tasting rooms

16. Romantic Napa Escape Prime Location King Bed, Private Patio & Pool

Romantic Napa Escape Prime Location King Bed, Private Patio & Pool
3.0 star property
Napa
The price is CA $221
CA $1,033 total
includes taxes & fees
Sep 13 - Sep 14
Romantic Napa Escape Prime Location King Bed, Private Patio & Pool

17. Stylish Napa Retreat | Patio • W/D • 10 Min to DT

Stylish Napa Retreat | Patio • W/D • 10 Min to DT
Napa
10.0 out of 10, Exceptional, (7 reviews)
"The stay was great!"
United States
Jason H.
The price is CA $360
CA $691 total
includes taxes & fees
Sep 8 - Sep 9
Stylish Napa Retreat | Patio • W/D • 10 Min to DT

18. Explore the Beauty of Napa Valley - Hike, Bike, Paddle, Wine and Dine

Explore the Beauty of Napa Valley - Hike, Bike, Paddle, Wine and Dine
Napa
9.8 out of 10, Exceptional, (33 reviews)
"Great place beautiful property all around just a really nice day"
United States
Jim
The price is CA $303
CA $584 total
includes taxes & fees
Sep 7 - Sep 8
Explore the Beauty of Napa Valley - Hike, Bike, Paddle, Wine and Dine

19. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (28 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 $135
CA $341 total
includes taxes & fees
Sep 13 - Sep 14
2 Hidden Wine Country Gem Upstairs Unit

20. Silverado Napa Luxury 1 Bedroom

Silverado Napa Luxury 1 Bedroom
Napa
8.8 out of 10, Excellent, (9 reviews)
"It was a great place to stay! The pool was fabulous! Host was also wonderful answering questions very quickly!! We will be staying there again!!"
United States
Kimberly
The price is CA $212
CA $417 total
includes taxes & fees
Sep 9 - Sep 10
Silverado Napa Luxury 1 Bedroom
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.