Holiday Rentals in Oakville

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Our top choices for Oakville holiday rentals

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"Yes, our little buddy was welcome!"
United States
Doug G.
The price is €353
includes taxes & fees
18 May - 19 May
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,375 reviews)
"Very friendly staff!"
Canada
Holly
The price is €133
includes taxes & fees
19 May - 20 May
RiverPointe Napa Valley Resort

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, (3 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveller
The price is €353
includes taxes & fees
18 May - 19 May
Escape to wine country in your independent cottage in downtown Calistoga

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
8.0 out of 10, Very good, (1 review)
"Muy bonito diseño interior en ambos la recepción y el cuarto."
Mexico
Tara
The price is €315
includes taxes & fees
9 Jun - 10 Jun
Sonoma Stonehouse, Wine Country Vibes

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, (39 reviews)
"Perfect little cottage within walking distance to everything in downtown Calistoga! Bed was so comfy and the fireplace made it feel extra cozy. We definitely want to stay here again!"
United States
Cameron D.
The price is €296
includes taxes & fees
11 Jun - 12 Jun
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

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, (73 reviews)
"Loved our stay!!"
United States
kristen s.
The price is €459
includes taxes & fees
18 May - 19 May
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Available * Downtown Napa- Beautifully Remodeled --2Bedroom 2 Bathroom Home

Available * Downtown Napa- Beautifully Remodeled --2Bedroom 2 Bathroom Home
Central Napa
10.0 out of 10, Exceptional, (303 reviews)
"Great stay. Very close to downtown and the Napa train!!"
United States
Cissy C.
The price is €438
includes taxes & fees
15 Jun - 16 Jun
Available * Downtown Napa- Beautifully Remodeled --2Bedroom 2 Bathroom Home

Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (85 reviews)
"Great house in a perfect location. Short distance to Jack London State Park, various wineries, and walking distance to lovely restaurants near by. We enjoyed our long weekend and will definitely stay here again when we're up in the area!"
United States
sandra h.
The price is €473
includes taxes & fees
18 May - 19 May
Glen Ellen Retreats Hot Tub Cottage

Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa

Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa
Napa
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was extremely nice and complete with all you could need while in vacation with your family. Everything was very comfortable. Kitchen was complete for us to cook our dinners and breakfasts. Krista, our host, was always available with constant communication with us. Lovely place to stay to visit Napa. "
United States
Rene Arturo Chen
The price is €425
includes taxes & fees
19 May - 20 May
Napa Escape, Patio, Washer/Dryer, 10 MIN 2 DT Napa

Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (11 reviews)
The price is €338
includes taxes & fees
16 Jun - 17 Jun
Cozy Wine Country Guesthouse with Private Pool & Yard

Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (163 reviews)
"Absolutely loved our time at the Glen Ellen retreat. The home is so cozy and welcoming. "
United States
Amanda D.
The price is €446
includes taxes & fees
18 May - 19 May
Glen Ellen Retreats Coastal Cottage

When in Glen | Panoramic View | Pool / Hot Tub

When in Glen | Panoramic View | Pool / Hot Tub
Glen Ellen
10.0 out of 10, Exceptional, (17 reviews)
"Clean, beautiful views"
United States
Carol Y.
The price is €894
includes taxes & fees
9 Jun - 10 Jun
When in Glen | Panoramic View | Pool / Hot Tub

Bright & Stylish Home Stay Minutes from Wineries

Bright & Stylish Home Stay Minutes from Wineries
Petaluma
10.0 out of 10, Exceptional, (3 reviews)
"Host was very responsive to messages."
United States
Kelly P.
Bright & Stylish Home Stay Minutes from Wineries

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (77 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is €472
includes taxes & fees
20 May - 21 May
Glen Ellen Retreats Sunset Cottage

Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun

Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun
Southwest Santa Rosa
9.8 out of 10, Exceptional, (61 reviews)
"The house is beautiful and clean and very accommodating!"
United States
Marcie N.
The price is €564
includes taxes & fees
25 May - 26 May
Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (75 reviews)
"We stayed for a girls weekend for a napa get away. and we brought the dog and it was a great stay. And clean too. Easy for a home base. And it was affordable. Would stay again "
United States
Valerie C.
The price is €354
includes taxes & fees
1 Jun - 2 Jun
Wine Country Cottage in downtown Santa Rosa, CA

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is €235
includes taxes & fees
18 May - 19 May
2 Hidden Wine Country Gem Upstairs Unit

Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown

Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown
Petaluma
9.8 out of 10, Exceptional, (110 reviews)
"This was hands-down, one of my favorite VRBO‘s!!!! 5 star service gorgeous property, incredible amenities. "
United States
Jessieca M.
The price is €238
includes taxes & fees
18 May - 19 May
Petaluma Wine Country relaxing get away w/salt water pool/ spa close to downtown

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is €245
includes taxes & fees
1 Jun - 2 Jun
Charming King Cottage

The Palmer Farmhouse Pool Spa Putting Sauna Walk to DT

The Palmer Farmhouse Pool Spa Putting Sauna Walk to DT
Four Corners
10.0 out of 10, Exceptional, (42 reviews)
"Excellent house, clean, had everything we need. Good location. "
United States
Colin J.
The price is €1,367
includes taxes & fees
19 May - 20 May
The Palmer Farmhouse Pool Spa Putting Sauna Walk to DT
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

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, apart-hotels, 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 favorite 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 depends 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 €133 per night. Entering your travel dates in the search wizard you might find 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?

Chic Sonoma Oasis w/ Pool, Bocce, Hot Tub + Minutes to Downtown & Vineyards: This holiday home rental outside of Oakville offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 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 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.