Oakville Holiday Rentals

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Holiday Rentals in Oakville

RiverPointe Napa Valley Resort

3.0 star property
8.8 out of 10, Excellent, (1316)
"Love being close to the river."
The price is AU$217
includes taxes & fees
23 Sept - 24 Sept
RiverPointe Napa Valley Resort

As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

9.8 out of 10, Exceptional, (89)
"The house was phenomenal and we truly enjoyed our stay. The bedrooms all have large beds and bathrooms and are separate which provided nice privacy. The hot tub, common areas, and view were all amazing."
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (65)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

The Napa Residences

4.5 star property
The price is AU$635
includes taxes & fees
21 Sept - 22 Sept
The Napa Residences

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (131)
"Cozy Location for a Corporate retreat!"
The price is AU$5,122
includes taxes & fees
20 Sept - 21 Sept
Casa Bella Estate in Wine Country w/ New Pool!

Historic Cuneo Cottage Downtown Sonoma

9.4 out of 10, Exceptional, (87)
"We enjoyed staying in your Cuneo Cottage. Loved the history and pictures throughout the house and the proximity to the Plaza, hiking trail and Sebastiani Winery!! "
The price is AU$1,230
includes taxes & fees
27 Sept - 28 Sept
Historic Cuneo Cottage Downtown Sonoma

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

10.0 out of 10, Exceptional, (242)
"Loved the house and location! "
The price is AU$3,615
includes taxes & fees
6 Oct - 7 Oct
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate

10.0 out of 10, Exceptional, (9)
"The property was great for a decent sized group! Nicely located and provided excellent space and amenities."
The price is AU$2,409
includes taxes & fees
29 Sept - 30 Sept
Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (237)
"Truly one of the best rentals I’ve ever stayed in. The host is super responsive and easy to work with, the house is great and the views/outdoor space are absolutely incredible. Would love to return in the future! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

9.8 out of 10, Exceptional, (203)
"Stunning home on a beautiful property. "
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

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

2.0 star property
10.0 out of 10, Exceptional, (8)
"Beautiful property"
The price is AU$563
includes taxes & fees
29 Sept - 30 Sept
2 bed I Silverado Resort & Spa in Napa - Wine Town

Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

9.8 out of 10, Exceptional, (190)
"We loved our stay, the kitchen was full of supplies, and more! Kids enjoyed the pool and games. Great convenient location."
The price is AU$1,293
includes taxes & fees
23 Sept - 24 Sept
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (25)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is AU$617
includes taxes & fees
24 Sept - 25 Sept
Escape to Wine County in your independant Cottage in Downtown Calistoga

When in Glen | Sonoma | Panoramic Views | 3bed / 3bath

10.0 out of 10, Exceptional, (11)
"Beautiful homeSpacious Well appointedVery comfortable beds"
The price is AU$1,275
includes taxes & fees
23 Sept - 24 Sept
When in Glen | Sonoma | Panoramic Views | 3bed / 3bath

VINEYARD VIEW 4 BED/3 BATH W//HOT TUB PERFECT LOCATION FOR WINE TASTING

9.8 out of 10, Exceptional, (389)
"Amazing house for a Napa get away. Perfect location and best backyard views around!"
VINEYARD VIEW 4 BED/3 BATH W//HOT TUB PERFECT LOCATION FOR WINE TASTING

Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!

10.0 out of 10, Exceptional, (83)
"Had a great time!"
Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!

Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10

9.8 out of 10, Exceptional, (154)
"Our stay was perfect. Great communication and super accommodating!"
Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10

Charming Newcomb Cottage Downtown Sonoma

10.0 out of 10, Exceptional, (44)
"What an amazing stay. This cottage was stunning. It was in the perfect location. The town plaza was so beautiful! This cottage had everything we needed for an amazing trip! "
Charming Newcomb Cottage Downtown Sonoma

Sonoma Victorian in Heart of Sonoma

10.0 out of 10, Exceptional, (17)
"The Bancroft Inn was lovely. It was a short walk in to downtown Sonoma. The management team was great to work with and we would recommend a stay here. "
Sonoma Victorian in Heart of Sonoma

Amy's Place

10.0 out of 10, Exceptional, (11)
"We loved staying at this property. So convenient and walkable to downtown. Extremely clean and tastefully decorated. Will definitely stay here again. Highly recommend. "
Amy's Place
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

Find out more about Oakville

Everything you need to know about Oakville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oakville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakville holiday rentals we have selected for you start as low as AU$217 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville holiday 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 holiday.

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 holiday rental in Oakville?

Yes, there are holiday rentals in Oakville close to Folie a Deux, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Oakville has to offer?

Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!: This holiday home rental outside of Oakville is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 holiday rentals like in Oakville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakville. Holiday rentals offer amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.