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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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Oakville vacation rentals

A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

1. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,534 reviews)
"Great place to stay"
United States
Waldemar.
$119 nightly
The price is $137
Nov 11 - Nov 12
Total with taxes and fees
RiverPointe Napa Valley Resort
An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

2. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (43 reviews)
"Nice, great location."
United States
Juan
$448 nightly
The price is $515
Nov 17 - Nov 18
Total with taxes and fees
The Napa Residences
Property grounds

3. Spacious Honeymoon Suite

Spacious Honeymoon Suite
Downtown St. Helena
10.0 out of 10, Exceptional, (23 reviews)
"Great location, clean, and quiet. We could walk to several great restaurants! "
United States
Cheryl Z.
$384 nightly
The price is $435
Nov 2 - Nov 3
Total with taxes and fees
Spacious Honeymoon Suite
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

4. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (179 reviews)
"Awesome place to stay! "
United States
Amanda D.
$466 nightly
The price is $515
Oct 20 - Oct 21
Total with taxes and fees
Glen Ellen Retreats Coastal Cottage
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

5. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (101 reviews)
"Enjoyed our stay! Walkable to restaurants, groceries, hiking trails. Well stocked kitchen for cooking. Beds and pillows extremely comfortable. The place was spotless and well maintained. Would stay here again and highly recommend!"
United States
Amy
$494 nightly
The price is $546
Oct 19 - Oct 20
Total with taxes and fees
Glen Ellen Retreats Hot Tub Cottage
A hot tub on a wooden deck with string lights, outdoor furniture, and a barbecue grill.

6. The Harvard House: Napa, Hot Tub + Detached Studio

The Harvard House: Napa, Hot Tub + Detached Studio
Napa
9.4 out of 10, Exceptional, (55 reviews)
"Location was great. Our party made comment time and time again on how open the gathering space was for us to hang out as a group. We jammed so much that we didn’t get a chance to take advantage of the outdoor space. Hopefully next time."
United States
Hilda K.
$1,081 nightly
The price is $1,081
Nov 5 - Nov 6
Total with taxes and fees
The Harvard House: Napa, Hot Tub + Detached Studio
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

7. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (87 reviews)
"Great house and location. Very clean and comfortable. Perfect location as a base for visiting wineries. Highly recommend"
United States
patrick s.
$466 nightly
The price is $515
Oct 19 - Oct 20
Total with taxes and fees
Glen Ellen Retreats Sunset Cottage
Exterior

8. Downtown Cottage House

Downtown Cottage House
Downtown St. Helena
9.6 out of 10, Exceptional, (25 reviews)
"The location of the property is the best. "
United States
Kim B.
$1,044 nightly
The price is $1,181
Nov 16 - Nov 17
Total with taxes and fees
Downtown Cottage House
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

9. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (23 reviews)
"Awesome stay. Perfect for three couples. Great support and communication from hosts and management team. Couldn’t have asked for better."
United States
Phillip T.
$1,163 nightly
The price is $1,283
Nov 2 - Nov 3
Total with taxes and fees
Cloud 9 - A Retreat for Bliss and Happiness
A spacious indoor area with a patterned floor, wooden staircase, and large windows offering a view of the outdoors.

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

Stylish Napa Retreat | Patio • W/D • 10 Min to DT
Napa
9.8 out of 10, Exceptional, (8 reviews)
"The stay was great!"
United States
Jason H.
$408 nightly
The price is $442
Oct 26 - Oct 27
Total with taxes and fees
Stylish Napa Retreat | Patio • W/D • 10 Min to DT
A living room with a grey sofa, a coffee table, a fireplace, a TV mounted on the wall, and a balcony with a view of greenery.

11. 2BR Near Wineries, Golf Course View, Parking

2BR Near Wineries, Golf Course View, Parking
4.0 star property
Napa
$861 nightly
The price is $990
Oct 22 - Oct 23
Total with taxes and fees
2BR Near Wineries, Golf Course View, Parking
A covered outdoor seating area with a pergola, a hot tub, and a wooden deck.

12. Outdoor Sonoma Escape with Hot Tub and Large Yard

Outdoor Sonoma Escape with Hot Tub and Large Yard
Fetters Hot Springs-Agua Caliente
10.0 out of 10, Exceptional, (21 reviews)
"Lovely property, very nice yard, enjoyed the hot tub."
United States
Innesa L.
$538 nightly
The price is $538
Oct 21 - Oct 22
Total with taxes and fees
Outdoor Sonoma Escape with Hot Tub and Large Yard
A two-story house with a garage, a balcony, and a driveway.

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

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
$256 nightly
The price is $283
Oct 19 - Oct 20
Total with taxes and fees
King bedroom #1 Wine Country Gateway With BBQ+Billiards
Two wicker chairs with blue patterned cushions on a wicker table, each with a glass of red wine and a vase of white flowers.

14. Ambrose Bierce House

Ambrose Bierce House
Downtown St. Helena
9.8 out of 10, Exceptional, (29 reviews)
"The innkeepers were outstanding. The facility is wonderful - easy location to enjoy St. Helena and Napa Valley."
United States
Steve H.
$1,533 nightly
The price is $1,742
Oct 19 - Oct 20
Total with taxes and fees
Ambrose Bierce House
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view of greenery outside.

15. 1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9

1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9
Downtown St. Helena
10.0 out of 10, Exceptional, (286 reviews)
"Absolutely amazing location and home! Highly recommend."
United States
Cruz P.
$1,656 nightly
The price is $1,874
Oct 19 - Oct 20
Total with taxes and fees
1 Block To St Helena Main Street Shops, Restaurants! Avail Sept 27-1, Oct 5-9
A spacious living room with a high ceiling, a large painting, and a view of the outdoors.

16. Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views

Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
Kenwood
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home & property. Great location. We thoroughly enjoyed our stay! "
United States
Laura G.
$1,105 nightly
The price is $1,221
Oct 27 - Oct 28
Total with taxes and fees
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
Exterior

17. Silverado Napa Luxury 1 Bed Jr. Suite

Silverado Napa Luxury 1 Bed Jr. Suite
Napa
9.8 out of 10, Exceptional, (69 reviews)
"Spacious room with amenities nearby. Great location for visiting the wineries. Safe environment. It was a very comfortable stay. We would definitely return here again!"
United States
Tim P.
$243 nightly
The price is $243
Nov 18 - Nov 19
Total with taxes and fees
Silverado Napa Luxury 1 Bed Jr. Suite
A round table with a bottle of wine, two glasses, and a tray of food. Two chairs with patterned cushions are positioned around the table.

18. Cozy Premium Jr. Suite, In Beautiful Napa Valley -Perfect for Couples

Cozy Premium Jr. Suite, In Beautiful Napa Valley -Perfect for Couples
Napa
9.2 out of 10, Wonderful, (55 reviews)
"We love staying at the Silverado Resort ♥️ it perfect for a week or weekend getaway. Can’t wait to revisit."
United States
Kim S.
$428 nightly
The price is $465
Oct 19 - Oct 20
Total with taxes and fees
Cozy Premium Jr. Suite, In Beautiful Napa Valley -Perfect for Couples
A hallway with a wooden door, a chair, a lamp, and a painting on the wall.

19. Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Downtown St. Helena
10.0 out of 10, Exceptional, (277 reviews)
"Beautiful rustic property. Great for family gatherings with large kitchen and open layout. It’s very close to St. Helena downtown where you could walk ~10 mins and even right across the street from Beringer. The Host was very responsive when we were checking in and helped us resolve our user-error quickly. Our family enjoyed our brief time here, and we would consider coming back for another reunion in the future."
United States
David
$1,942 nightly
The price is $2,197
Nov 1 - Nov 2
Total with taxes and fees
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
An outdoor deck with a round table and chairs, a sofa, and a fire pit.

20. Sonoma Gem! Modern. Serene. Wine Retreat w/ HOT TUB!

Sonoma Gem! Modern. Serene. Wine Retreat w/ HOT TUB!
Verano
10.0 out of 10, Exceptional, (16 reviews)
"This is a perfect place for a family to stay."
United States
Nachyun
$694 nightly
The price is $767
Oct 20 - Oct 21
Total with taxes and fees
Sonoma Gem! Modern. Serene. Wine Retreat w/ HOT TUB!
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

Silverado Resort

Silverado Resort

10/10 Excellent
"Beautiful property"
Melanie 2-night trip
Posted 1 hour ago
Silverado Resort

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 $137 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.

Explore a world of travel with Expedia

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.