Search Vacation Homes in Oakville

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 589 Vacation Homes in Oakville with updated reviews, rates, and availability.

Beautiful Home in Northwest Napa

10.0 out of 10, Exceptional, (25)
"Great location in a quiet neighborhood. Host was super responsive throughout the visit. Perfect house for our family vacation to Napa Valley! "
Beautiful Home in Northwest Napa

Enjoy A Modern Hacienda In The Heart Of Sonoma!

9.8 out of 10, Exceptional, (161)
"The property was very much like it was advertised - nice gathering spaces and well-stocked kitchen for dishes and cookware. There could have been more towels to fit the number of guests allowed and there were no blankets. For the cooler seasons, some throw blankets would be good. The property is in a nice area with easy access to everything in sonoma. It was nice and quiet at night. We would definitely stay there again."
Enjoy A Modern Hacienda In The Heart Of Sonoma!

Napa Valley Modern Bungalow

10.0 out of 10, Exceptional, (37)
"We absolute loved our stay. So cozy, clean and inviting. Highly recommend! "
Napa Valley Modern Bungalow

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

9.8 out of 10, Exceptional, (173)
"We had an amazing time in Napa. The house had everything anyone might need and location was perfect. Hosts were very responsive when there was a small glitch. Would definitely stay here again!"
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

Wine Country Backyard Escape

10.0 out of 10, Exceptional, (13)
"We had two toddlers running around the house and backyard. They loved it. Was a wonderful place for us to relax and enjoy wine country"
Wine Country Backyard Escape

Central Napa Gem - Steps from Downtown Napa & Wineries

2.0 star property
10.0 out of 10, Exceptional, (2)
"This place was perfectly situated to explore downtown and go wine tasting. We loved the cozy house and enjoyed our days there. We have already said we would book this place again in the future. "
Central Napa Gem - Steps from Downtown Napa & Wineries

Kenwood Vista by AvantStay | 7acres w/ Pool, Fire Pit, Vineyard Views

Kenwood Vista by AvantStay | 7acres w/ Pool, Fire Pit, Vineyard Views

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

10.0 out of 10, Exceptional, (217)
"The drive in and out of the property will amaze from the start! The property is wonderfully situated a top a quiet and peaceful Sonoma mountain with fantastic views in all directions. The house is beautifully architected and great for a large group, including the guest house. Game room, hot tub, chef’s kitchen and fire places made for an excellent stay. Kenwood Winery was our fave right near the house. Host was excellent with any questions we had. Our group was super pleased! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

1 Acre with 3 homes in the heart of wine country with last minute specials!

9.6 out of 10, Exceptional, (28)
"A group of 11 stayed at this property over a long weekend and enjoyed our stay. The location was great, everything we needed was very easy to get to. It was nice that we could all stay together while still having our space when we needed. "
1 Acre with 3 homes in the heart of wine country with last minute specials!

Winepress Cozy Getaway

10.0 out of 10, Exceptional, (86)
"This is a beautifully decorated and maintained unit. Close to downtown. Property manager is top tier. Highly recommend. "
Winepress Cozy Getaway

Calistoga Vineyard House

10.0 out of 10, Exceptional, (33)
"This was a killer place and will be back. "
Calistoga Vineyard House

Annadel House Retreat- Stunning Wine Country Luxe!

9.4 out of 10, Exceptional, (27)
"We had a fantastic time with five ladies from across the country to celebrate two 50th birthdays. The place was fantastic – the kitchen was great for cooking a meal and for coffee in the morning. Plenty of space to spread out & the beds were comfortable!!!! We had a minor issue with the showerheads being scaled with water. We reached out to the property owner and while they didn’t fix it on our visit 6 pounds of salt were dropped off so I assume they are fixing it for the next guest. Highly...
The price is AED 1,245
AED 2,659 total
includes taxes & fees
14 Jan - 15 Jan
Annadel House Retreat- Stunning Wine Country Luxe!

Modern Napa 3BD Wine Country Escape w/ Pool & Spa

9.6 out of 10, Exceptional, (28)
"Great location. Had some cobwebs around. Needs more thorough cleaning and more wash rags and towels. "
Modern Napa 3BD Wine Country Escape w/ Pool & Spa

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

10.0 out of 10, Exceptional, (222)
"This is a beautiful home in a quaint location to build special memories. We will definitely return!!"
The price is AED 6,060
AED 7,706 total
includes taxes & fees
14 Jan - 15 Jan
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

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

9.8 out of 10, Exceptional, (187)
"The property was as advertised with ample space for all guests. There was supposed to be a twin bed in the king bed room but otherwise, we had the beds needed/expected. There was a plumbing issue with one of the bathrooms (water leaking to ceiling below) that needs to be addressed. All else was good."
The price is AED 1,466
AED 3,243 total
includes taxes & fees
2 Feb - 3 Feb
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (239)
"Wonderful property and location. Short scenic drive to several great wineries and restaurants. House was exactly as advertised. Drive through vineyards to get back to the property a nice touch"
New Modern House in Sonoma Valley's Best Area

Spanish Bungalow with Hot Tub! Close to downtown and easy access to Wine Country

9.8 out of 10, Exceptional, (266)
"We had a great stay here, mattresses were comfortable, and everything was clean and comfortable. Kitchen had the basics, there was a great Taco restaurant a few doors down, downtown Napa was a 10-15 min walk. Hot tub was lovely, but you will want to preheat it. It is elevated from the patio, so it takes two to remove and replace the cover. We had a little trouble with the controls, but there were some troubleshooting tips in the house binder. (We did have to turn on the outdoor...
The price is AED 716
AED 1,542 total
includes taxes & fees
15 Jan - 16 Jan
Spanish Bungalow with Hot Tub! Close to downtown and easy access to Wine Country

Home near Sonoma & Calistoga in heart of Wine Country

9.4 out of 10, Exceptional, (34)
"Simple property in a very quiet neighborhood. It is nothing fancy, but the price compared to everything else I could find for the same date. We needed three rooms with at least a double or larger for a long weekend stay. This fit the bill. The only odd thing to note is that some of the water valves are backwards. It didn't really impact our stay however. We would stay hear again."
Home near Sonoma & Calistoga in heart of Wine Country

Charm and Modern Luxury in Heart of Wine Country

10.0 out of 10, Exceptional, (132)
"House was clean. No issues with anything. Check in/out was easy and communication was just right. We’d stay here again "
Charm and Modern Luxury in Heart of Wine Country

Napa Valley: St Helena Designer Home & Guest House + Spool + Peloton Bike/Tread

10.0 out of 10, Exceptional, (111)
"Ideal location in St. Helena to use a base for wine tasting. Everything you need is walking distance. "
Napa Valley: St Helena Designer Home & Guest House + Spool + Peloton Bike/Tread
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.
Don't see what you're looking for?
See all available properties in Oakville
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Oakville

RiverPointe Napa Valley Resort

3.0 star property
8.6 out of 10, Excellent, (1223)
"The house is overall charming but has several issues that need attention: - There was an unpleasant smell in the bathroom. - The bathroom wasn't cleaned properly, as the tub had black hair. - The thermostat was challenging to figure out, and it was cold inside. - Equipment noises could be heard coming from the attic. - There were no power outlets near the nightstands in the bedroom to charge phones. - The TVs were outdated, making it impossible to watch YouTube. - There was no lighting above...
RiverPointe Napa Valley Resort

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

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Beautiful Home in Northwest Napa

10.0 out of 10, Exceptional, (25)
"Great location in a quiet neighborhood. Host was super responsive throughout the visit. Perfect house for our family vacation to Napa Valley! "
Beautiful Home in Northwest Napa
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.