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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Oakville holiday rentals

An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

1. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (45 reviews)
"A very comfortable bed and beautiful pool setting in Napa Valley!"
United States
David
The price is £353
includes taxes & fees
12 Nov - 13 Nov
The Napa Residences
A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

2. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,561 reviews)
"Great place to stay"
United States
Waldemar.
The price is £114
includes taxes & fees
15 Nov - 16 Nov
RiverPointe Napa Valley Resort
Exterior

3. Silverado Napa Luxury 1 Bed Jr. Suite

Silverado Napa Luxury 1 Bed Jr. Suite
Napa
9.6 out of 10, Exceptional, (72 reviews)
"I was shocked by how big the space was! So easy to find, the grounds are well taken care of, super clean and stocked with just about anything you’d need. The perfect stay!"
United States
Shayna
The price is £156
includes taxes & fees
7 Dec - 8 Dec
Silverado Napa Luxury 1 Bed Jr. Suite
A large, white, two-story building with a symmetrical facade, surrounded by well-maintained lawns and palm trees.

4. Cozy Napa Escape Silverado Resort

Cozy Napa Escape Silverado Resort
Napa
9.6 out of 10, Exceptional, (18 reviews)
"Loved to stay at this property. It was a short Uber ride to lots of wineries and the resort was so beautiful. Super comfy and convenient. The parking was easy, super clean and the check in was so easy."
United States
Carla
The price is £171
includes taxes & fees
17 Nov - 18 Nov
Cozy Napa Escape Silverado Resort
A large, white building with a symmetrical facade, surrounded by well-maintained lawns and palm trees.

5. 1 bed | 1 bath | Silverado Resort Experience

1 bed | 1 bath | Silverado Resort Experience
Napa
9.8 out of 10, Exceptional, (23 reviews)
"Great location on the property and close to all the sites Napa has to offer. "
United States
Patricia L.
The price is £174
includes taxes & fees
11 Nov - 12 Nov
1 bed | 1 bath | Silverado Resort Experience
A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

6. Modern Organic 3BR Oasis w/ Creek&Near State Park

Modern Organic 3BR Oasis w/ Creek&Near State Park
Kenwood
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is £378
includes taxes & fees
11 Nov - 12 Nov
Modern Organic 3BR Oasis w/ Creek&Near State Park
A modern living room with a sofa, coffee table, and a fireplace. There is a television mounted on the wall and a large window with a view of a green landscape.

7. Napa relaxation at its finest at Silverado Resort

Napa relaxation at its finest at Silverado Resort
Napa
10.0 out of 10, Exceptional, (7 reviews)
"Place was great, wish we could’ve stayed longer. "
United States
Jennifer C.
The price is £221
includes taxes & fees
1 Dec - 2 Dec
Napa relaxation at its finest at Silverado Resort
Exterior

8. 1 bed 1 bath Silverado Resort Experience Jr. Suite Condo

1 bed 1 bath Silverado Resort Experience Jr. Suite Condo
Napa
9.6 out of 10, Exceptional, (41 reviews)
"This unit is in a wonderful location and the environment and grounds are beautiful and serene!"
United States
Ann B.
The price is £184
includes taxes & fees
6 Dec - 7 Dec
1 bed 1 bath Silverado Resort Experience Jr. Suite Condo
Living area

9. 2 bed I Silverado Resort & Spa in Napa - Wine Town

2 bed I Silverado Resort & Spa in Napa - Wine Town
Napa
10.0 out of 10, Exceptional, (17 reviews)
"Great value, resort is beautiful"
United States
Jack K.
The price is £225
includes taxes & fees
11 Nov - 12 Nov
2 bed I Silverado Resort & Spa in Napa - Wine Town
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

10. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (182 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is £404
includes taxes & fees
11 Nov - 12 Nov
Glen Ellen Retreats Coastal Cottage
A spacious indoor area with a patterned floor, wooden staircase, and large windows offering a view of the outdoors.

11. Stylish Napa Retreat | Patio • W/D • 10 Min to DT

Stylish Napa Retreat | Patio • W/D • 10 Min to DT
Napa
9.8 out of 10, Exceptional, (9 reviews)
"The stay was great!"
United States
Jason H.
The price is £345
includes taxes & fees
11 Nov - 12 Nov
Stylish Napa Retreat | Patio • W/D • 10 Min to DT
A sliding glass door leading to an outdoor deck with a wooden bench, a table, and a chair.

12. Fireside Sips & Oak Dreams in Sonoma Valley

Fireside Sips & Oak Dreams in Sonoma Valley
Glen Ellen
10.0 out of 10, Exceptional, (11 reviews)
"We loved our stay in Glen Ellen! The space was perfect for our family of 4! It was very well stocked! Our host was wonderful and extremely informative about the area."
United States
Kristin B.
The price is £334
includes taxes & fees
15 Nov - 16 Nov
Fireside Sips & Oak Dreams in Sonoma Valley
A spacious indoor area with a tiled floor, a staircase, and large windows offering a view of the outdoors.

13. Poolside Retreat | Patio | 10 Min to DT

Poolside Retreat | Patio | 10 Min to DT
Napa
10.0 out of 10, Exceptional, (32 reviews)
"Nice place. Easy to book, checkin and checkout."
United States
Stephen G.
The price is £282
includes taxes & fees
11 Nov - 12 Nov
Poolside Retreat | Patio | 10 Min to DT
A patio area with outdoor furniture, a pergola with string lights, and a stone fireplace.

14. Cottage at Main Street Farmhouse!

Cottage at Main Street Farmhouse!
McPherson
10.0 out of 10, Exceptional, (99 reviews)
"Excellent location and cozy!"
United States
Lori
The price is £245
includes taxes & fees
11 Nov - 12 Nov
Cottage at Main Street Farmhouse!
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

15. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (89 reviews)
"Great house and location. Very clean and comfortable. Perfect location as a base for visiting wineries. Highly recommend"
United States
patrick s.
The price is £409
includes taxes & fees
18 Nov - 19 Nov
Glen Ellen Retreats Sunset Cottage
A modern living room with a fireplace, a television, a sofa, a coffee table, and a view of a golf course through large windows.

16. Wine Country Escape at Silverado in Napa!

Wine Country Escape at Silverado in Napa!
Napa
9.0 out of 10, Wonderful, (55 reviews)
"Great location in Napa! I would stay here again."
United States
Erin Y.
The price is £320
includes taxes & fees
1 Dec - 2 Dec
Wine Country Escape at Silverado in Napa!
A living room with a fireplace, a sofa set, a coffee table with a bottle and glasses, and a television displaying a golf scene.

17. Incredible Golf Course View at Silverado

Incredible Golf Course View at Silverado
Napa
8.6 out of 10, Excellent, (40 reviews)
"Kitchen and sitting area was very comfortable."
United States
Greg S.
The price is £334
includes taxes & fees
12 Nov - 13 Nov
Incredible Golf Course View at Silverado
A wooden deck with potted plants, a bench, and a building with large windows and a door.

18. The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!

The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
Glen Ellen
9.8 out of 10, Exceptional, (139 reviews)
"Great home, hosts, and area. We loved everything about the trip and will be back in the fall. Thank you for the wonderful experience."
United States
Robert K.
The price is £389
includes taxes & fees
19 Nov - 20 Nov
The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

19. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (101 reviews)
"Enjoyed our stay! Walkable to restaurants, groceries, hiking trails. Well stocked kitchen for cooking. Beds and pillows extremely comfortable. The place was spotless and well maintained. Would stay here again and highly recommend!"
United States
Amy
The price is £443
includes taxes & fees
11 Nov - 12 Nov
Glen Ellen Retreats Hot Tub Cottage
A spacious kitchen with a large island, a dining area with a sofa and chairs, and a view of the outdoors.

20. Silverado Napa Breath Taking Remodel 3 bed 2 bath

Silverado Napa Breath Taking Remodel 3 bed 2 bath
Napa
9.8 out of 10, Exceptional, (14 reviews)
"Clean and pet friendly place"
United States
Tracie T.
The price is £284
includes taxes & fees
1 Dec - 2 Dec
Silverado Napa Breath Taking Remodel 3 bed 2 bath
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

An outdoor patio area with wicker furniture, a stone fire pit, and a pergola structure.
Napa Valley Lodge

Napa Valley Lodge

Napa Valley Lodge
Yountville

10/10 Excellent

Great!
United Kingdom
Peter
Reviewed February 8, 2026
Napa Valley Lodge

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 £113 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?

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella: This holiday home rental outside of Oakville is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 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 library 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.