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

Oakville Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Oakville holiday rentals

Exterior

RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,412 reviews)
"Stayed here with parents for a weekend getaway. Was really nice, spacious accommodation and had everything we needed for our stay."
United States
Claudia
The price is HK$874
HK$1,276 total
includes taxes & fees
19 Jul - 20 Jul
RiverPointe Napa Valley Resort
Exterior

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is HK$2,422
HK$3,240 total
includes taxes & fees
16 Jul - 17 Jul
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is HK$2,422
HK$3,280 total
includes taxes & fees
16 Jul - 17 Jul
Escape to wine country in your independent cottage in downtown Calistoga
Internet

Lux Napa Escape King Bed Steps to Wineries

Lux Napa Escape King Bed Steps to Wineries
2.0 star property
Napa
The price is HK$966
HK$4,708 total
includes taxes & fees
16 Jul - 17 Jul
Lux Napa Escape King Bed Steps to Wineries
2 bedrooms, iron/ironing board, travel cot, free WiFi

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (80 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is HK$1,959
HK$4,038 total
includes taxes & fees
19 Jul - 20 Jul
Glen Ellen Retreats Sunset Cottage
Exterior

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (42 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is HK$2,579
HK$3,488 total
includes taxes & fees
20 Jul - 21 Jul
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Terrace/patio

Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (166 reviews)
"Fantastic getaway location. What a lovely town Glen Ellen is and convenient walking distance to coffee, shops and food as well as any sundries you may need. Highly recommend it as a great getaway great getaway."
United States
Randall
The price is HK$1,959
HK$4,038 total
includes taxes & fees
19 Jul - 20 Jul
Glen Ellen Retreats Coastal Cottage
Terrace/patio

Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (90 reviews)
"Beautiful home and very quiet town. Enjoyed my stay! "
United States
Adrian P.
The price is HK$2,155
HK$4,258 total
includes taxes & fees
16 Jul - 17 Jul
Glen Ellen Retreats Hot Tub Cottage
TV, fireplace

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (74 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is HK$2,265
HK$4,813 total
includes taxes & fees
20 Jul - 21 Jul
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Outdoor dining

Spacious 2BR at Silverado | Pool Access | Patio

Spacious 2BR at Silverado | Pool Access | Patio
Napa
10.0 out of 10, Exceptional, (5 reviews)
"Krista was a dream to work with and the condo was amazing. It had everything we needed for our stay."
United States
Mara F.
The price is HK$3,358
HK$6,252 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 2BR at Silverado | Pool Access | Patio
Outdoor pool, a heated pool

Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (20 reviews)
"This was the perfect cozy stay for a rainy weekend- a great pool and yard for all seasons."
United States
Anand D.
The price is HK$2,610
HK$2,947 total
includes taxes & fees
27 Jul - 28 Jul
Cozy Wine Country Guesthouse with Private Pool & Yard
Outdoor dining

Cottage at Main Street Farmhouse!

Cottage at Main Street Farmhouse!
McPherson
10.0 out of 10, Exceptional, (93 reviews)
"Excellent location and cozy!"
United States
Lori
The price is HK$1,646
HK$2,875 total
includes taxes & fees
19 Jul - 20 Jul
Cottage at Main Street Farmhouse!
TV, fireplace

Bright & Stylish Home Stay Minutes from Wineries

Bright & Stylish Home Stay Minutes from Wineries
Petaluma
9.6 out of 10, Exceptional, (4 reviews)
"The house was very roomy and comfortable for a group. We enjoyed the open downstairs and private backyard. Location was great and the stay worked out well."
United States
Chris J.
The price is HK$2,019
HK$4,049 total
includes taxes & fees
21 Jul - 22 Jul
Bright & Stylish Home Stay Minutes from Wineries
Coffee/tea maker, fridge, microwave, oven

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
Santa Rosa
9.4 out of 10, Exceptional, (26 reviews)
"Great place to stay and convenient to everything we wanted to do. Wish we could’ve stayed longer!! "
United States
kara l.
The price is HK$1,764
HK$4,209 total
includes taxes & fees
20 Jul - 21 Jul
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
Terrace/patio

The Harvard House: Napa, Hot Tub + Detached Studio

The Harvard House: Napa, Hot Tub + Detached Studio
Napa
9.4 out of 10, Exceptional, (53 reviews)
"My family felt at home every time returned to Harvard House after a Napa outing. The open layout is great for socializing and the house is well stocked. The location is excellent for wine tours and downtown restaurants and bars. The neighborhood also allows for easy morning walks. I would definitely stay again!"
United States
Shonda M.
The price is HK$2,980
HK$6,067 total
includes taxes & fees
20 Jul - 21 Jul
The Harvard House: Napa, Hot Tub + Detached Studio
Dining

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (84 reviews)
"Awesome pet friendly home with nice backyard, great location. Really enjoyed our two night stay in this well appointed home while visiting surrounding areas. Cynthia responded so quickly to any of our questions. Would love to stay here again! "
United States
Keri S.
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
1 bedroom, desk, iron/ironing board, free WiFi

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, (92 reviews)
"The host was wonderful- very responsive and accommodating. The location was perfect- walking distance to downtown. Also easy check-in and checkout process which was much appreciated. "
United States
Amy h.
The price is HK$1,842
HK$2,779 total
includes taxes & fees
19 Jul - 20 Jul
Luxe apartment close to wineries EZ walk downtown resturants and tasting rooms
Smart TV, fireplace, books, offices

Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
9.8 out of 10, Exceptional, (19 reviews)
"We loved our stay here, the spacious living space, gorgeous decor and lovely pool were the highlights. Can't wait to be back!"
United States
Amy M.
The price is HK$5,061
HK$11,534 total
includes taxes & fees
22 Jul - 23 Jul
Cloud 9 - A Retreat for Bliss and Happiness
Outdoor dining

Luxury 12-Sleeper: Pool, Hot Tub, Near Sonoma Plaza

Luxury 12-Sleeper: Pool, Hot Tub, Near Sonoma Plaza
Verano
10.0 out of 10, Exceptional, (7 reviews)
"Amazing property and very clean!"
United States
stephany g.
The price is HK$7,155
HK$12,991 total
includes taxes & fees
16 Jul - 17 Jul
Luxury 12-Sleeper: Pool, Hot Tub, Near Sonoma Plaza
2 bedrooms, desk, iron/ironing board, free WiFi

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (77 reviews)
"Overall a good place to stay in downtown Santa Rosa. "
United States
Stan R.
The price is HK$1,450
HK$3,137 total
includes taxes & fees
27 Jul - 28 Jul
Wine Country Cottage in downtown Santa Rosa, CA
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

Hotel Indigo Napa Valley by IHG

Hotel Indigo Napa Valley by IHG

10/10 Excellent
"Clean room,great staff."
Raymond 1-night trip
Posted less than an hour ago
Hotel Indigo Napa Valley by IHG

Find out more about Oakville

Search for holiday rentals in Oakville on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakville using one of the methods below:

  • View our selection of featured holiday rentals in Oakville
  • Use the map to find apartments and other holiday homes in the Oakville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakville while they last

Look no further and take a look at our great range of rental properties in Oakville!

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 Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10: This holiday home rental outside of Oakville offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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.