Oakville Holiday Rentals

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Holiday Rentals in Oakville

RiverPointe Napa Valley Resort
3.0 star property
8.6 out of 10, Excellent, 1,110 reviews
"Diamond in the rough! Great stay!"
The price is NZ$296
includes taxes & fees
10 Jun - 11 Jun
RiverPointe Napa Valley Resort
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
10.0 out of 10, Exceptional, 49 reviews
"We had a girls weekend at the Villa and it was absolutely amazing. Randy and his staff were super attentive to us and helped us the entire weekend. The house is absolutely amazing and very well stocked. We have zero complaints and would love to stay here again. Highly recommend utilizing all of the amenities that the house has to offer including the pickle ball court, gym, steam room, hot tub and wine cave! Thanks Randy for an amazing experience"
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
10.0 out of 10, Exceptional, 15 reviews
"12 of us traveled to Napa for my 40th birthday and we had THE BEST trip ever. The accommodations were lovely, spacious, clean and luxurious. The concierge was so responsive and helpful. The chefs were fantastic. I'd highly recommend this property. As a frequent traveler, I've stayed in many luxury rentals and this was by far my favorite."
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
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Sonoma's Best Cottages
3.5 star property
9.6 out of 10, Exceptional, 52 reviews
"Very cute and clean environment"
Sonoma's Best Cottages
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, 198 reviews
"This property is amazing and conveniently located."
The price is NZ$3,418
includes taxes & fees
5 Jun - 6 Jun
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Safari West
2.0 star property
9.4 out of 10, Exceptional, 219 reviews
"Incredible experience!"
The price is NZ$875
includes taxes & fees
5 Jun - 6 Jun
Safari West
The Corner Cottage ~ Downtown out your door with Private Vineyard
10.0 out of 10, Exceptional, 194 reviews
"We were very fortunate to find this relaxing retreat in Napa. We enjoyed walks around town and easy access to wineries."
The Corner Cottage ~ Downtown out your door with Private Vineyard
Spacious Home Near Downtown Napa
9.8 out of 10, Exceptional, 99 reviews
"Super easy to check in. Lots of space for a group. Extremely clean and well stocked with kitchen and bath items. Great gas stove if you like to cook. Only negative is street noise with front bedrooms. And, not to seem picky but it really needs a professional sprayer for the kitchen sink."
Spacious Home Near Downtown Napa
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, 210 reviews
"We loved staying here. The openness of the property and our luck in great weather provided an idyllic place to enjoy the company of our group. We walked to dinner each night and gazed at the night sky upon return."
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Romantic Getaway
10.0 out of 10, Exceptional, 59 reviews
"Great location for a trip to Napa valley! Very convenient to local wineries and restaurants. Hope to visit again in the future!"
Romantic Getaway
Relaxing & Romantic 1 bedroom Condo, in the Heart of Wine Country
9.6 out of 10, Exceptional, 69 reviews
"We very much enjoyed our respite for a couple of nights here at this condo that is well-positioned location-wise. It is clean, with coffee maker, comfortable bed, with respectfully quiet neighbors. The resort's store/gift shop/bakery has a good selection of food and drink and other items one might need. Would stay here again."
The price is NZ$646
includes taxes & fees
30 Jun - 1 Jul
Relaxing & Romantic 1 bedroom Condo, in the Heart of Wine Country
Pool, Spa, Huge Backyard, 3 Miles from Sonoma Square and 1 mile from Wineries
10.0 out of 10, Exceptional, 186 reviews
"Awesome spot to relax after a full day of wine tasting"
Pool, Spa, Huge Backyard, 3 Miles from Sonoma Square and 1 mile from Wineries
Beautiful Home in Northwest Napa
10.0 out of 10, Exceptional, 7 reviews
"We stayed for two nights to celebrate birthdays. There was tons of space, a nice outdoor seating area, it was spotless and close to amazing wineries. The perfect place for our trip!"
Beautiful Home in Northwest Napa
Cozy Retreat, Studio Apartment, City Permit VR09-0038.
9.6 out of 10, Exceptional, 244 reviews
"Great for Bottlerock. Close to the venue, parking onsite and small kitchen for breakfast prep."
Cozy Retreat, Studio Apartment, City Permit VR09-0038.
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
9.8 out of 10, Exceptional, 176 reviews
"This weekend was great for my big group of friends visiting and celebrating in the Sonoma and Napa. The hot tub was always warm, the house was stocked and the hosts were very accommodating!"
The price is NZ$1,847
includes taxes & fees
18 Jun - 19 Jun
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
Luxury Napa Valley Estate Surrounded by Vineyards
9.8 out of 10, Exceptional, 24 reviews
"Blown away with this home and property. Couldn’t have imagined how beautiful and spacious it was. The grounds were gorgeous"
Luxury Napa Valley Estate Surrounded by Vineyards
Lovely 6 acre property near charming Sonoma Square, Napa Valley and all wineries
10.0 out of 10, Exceptional, 47 reviews
"It was such a great place for our family of 6 to stay at the property and enjoyed our Thanksgiving holiday. The property is beautiful and has a lot to offer for everyone. We had such a wonderful time! We look forward to come back and visit again soon. Hopefully in the summer time, so we will get to enjoy the pool. The hosts were very friendly and responsive, we are really thankful for the whole experience! JC"
Lovely 6 acre property near charming Sonoma Square, Napa Valley and all wineries
Secluded Sonoma Country Retreat Views Pool-Spa-Vineyard-Olive Grove
10.0 out of 10, Exceptional, 122 reviews
"Our stay was excellent! This was the perfect place for our group of 10 to relax and catch up and also well located for exploring the area and of course the vineyard tours!"
Secluded Sonoma Country Retreat Views Pool-Spa-Vineyard-Olive Grove
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, 211 reviews
"The home was a welcome respite from hotel life. In just minutes you are off the beaten track enjoying a beautifully appointed home in the woods. We loved it!!"
New Modern House in Sonoma Valley's Best Area
Napa Valley Modern Bungalow
10.0 out of 10, Exceptional, 14 reviews
"Love this 2bed 1 bath cottage in Napa. Loved the decor and the bathroom has a heated floor. Close to all that you want to do in Napa. A bakery and breakfast/lunch place are very close for the am coffee run. Easy walk to the river. I would stay here again!"
Napa Valley Modern Bungalow
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See all available properties in Oakville
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.

Other types of properties in Oakville you may be interested in

Silverado Resort
4.0 star property
8.4 out of 10, Very good, 1,007 reviews
"The resort was beautiful. Our room was really nice and private. We enjoyed it and would stay again. Would only have liked to have had information in the room on the amenities available to us. "
The price is NZ$518
includes taxes & fees
10 Jun - 11 Jun
Silverado Resort
Fairmont Sonoma Mission Inn & Spa
5.0 star property
8.6 out of 10, Excellent, 1,005 reviews
"This upscale property is clean and feels very safe. The room was ample and everything worked properly. Service at the front desk and all other employees were friendly and helpful. The mineral pools were clean and the surrounding areas, cabanas, etc. were lovely."
The price is NZ$644
includes taxes & fees
10 Jun - 11 Jun
Fairmont Sonoma Mission Inn & Spa
The Sandman Hotel
3.0 star property
8.2 out of 10, Very good, 1,783 reviews
"Nice & clean. Parking right in front of my room. Convenient. 5 star for sure "
The price is NZ$224
includes taxes & fees
10 Jun - 11 Jun
The Sandman Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakville holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakville. 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 Oakville. 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 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 holiday 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 Oakville short-term rentals, that won’t be hard to do.

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?

Sonoma's Best Cottages: This holiday home rental outside of Oakville has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. In the wider area, you’ll find popular places such as Sonoma Plaza and Napa Valley Wine Train.

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.

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