Holiday Rentals in Oakville

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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

A spacious living room with a ceiling fan, wooden flooring, a sofa, a coffee table, and a television.

1. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,563 reviews)
"Great place to stay"
United States
Waldemar.
The price is €137
includes taxes & fees
15 Nov - 16 Nov
RiverPointe Napa Valley Resort
An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

2. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (46 reviews)
"A very comfortable bed and beautiful pool setting in Napa Valley!"
United States
David
The price is €463
includes taxes & fees
17 Nov - 18 Nov
The Napa Residences
A pool with a wooden deck and lounge chairs, surrounded by lush greenery and a mountainous backdrop.

3. Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more

Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more
Glen Ellen
9.4 out of 10, Exceptional, (12 reviews)
" Comfortable home and great host. "
United States
Garrett B.
Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more
A patio with a round table and chairs, surrounded by lush greenery and flowering plants.

4. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (183 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is €508
includes taxes & fees
13 Dec - 14 Dec
Glen Ellen Retreats Coastal Cottage
A backyard with a hot tub, a wooden deck, and a patio area with a table and chairs.

5. 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
Glen Ellen Retreats Hot Tub Cottage
A covered outdoor seating area with a pergola, a hot tub, and a wooden deck.

6. Outdoor Sonoma Escape with Hot Tub and Large Yard

Outdoor Sonoma Escape with Hot Tub and Large Yard
Fetters Hot Springs-Agua Caliente
9.8 out of 10, Exceptional, (23 reviews)
"Lovely property, very nice yard, enjoyed the hot tub."
United States
Innesa L.
The price is €461
includes taxes & fees
16 Nov - 17 Nov
Outdoor Sonoma Escape with Hot Tub and Large Yard
A poolside area with a fire pit, two sofas, and a view of a mountain landscape.

7. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (23 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.
Cloud 9 - A Retreat for Bliss and Happiness
A backyard with a wooden deck, a barbecue grill, and a small garden with various plants and flowers.

8. 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 €508
includes taxes & fees
14 Dec - 15 Dec
Glen Ellen Retreats Sunset Cottage
A tree with red flowers and green leaves.

9. North Napa Short Term Rental

North Napa Short Term Rental
Napa
9.2 out of 10, Wonderful, (19 reviews)
"Great location between downtown Napa and Yountville - perfectly placed! Quiet neighborhood. Comfortable spaces and beds!"
United States
Andy
The price is €656
includes taxes & fees
15 Nov - 16 Nov
North Napa Short Term Rental
A wooden deck with potted plants, a bench, and a building with large windows and a door.

10. 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 €495
includes taxes & fees
14 Dec - 15 Dec
The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
A building with a central entrance, surrounded by a well-maintained lawn and a variety of flowering plants.

11. Spacious 2BR at Silverado | Pool Access | Patio

Spacious 2BR at Silverado | Pool Access | Patio
Napa
9.8 out of 10, Exceptional, (7 reviews)
"Great spot!"
United States
Patrice M.
The price is €710
includes taxes & fees
17 Nov - 18 Nov
Spacious 2BR at Silverado | Pool Access | Patio
A building with a central entrance, surrounded by a well-maintained lawn and a variety of flowering plants.

12. 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 €504
includes taxes & fees
22 Nov - 23 Nov
Stylish Napa Retreat | Patio • W/D • 10 Min to DT
A wooden deck with a bench and a table, surrounded by trees and a pathway leading to a building.

13. 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.
Fireside Sips & Oak Dreams in Sonoma Valley
A white building with a wooden fence, a window, and a wall-mounted air conditioning unit.

14. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
8.0 out of 10, Very good, (3 reviews)
"Old but quaint. No amenities, no updates. Coffee cups looked like thrift shop purchases. Bed was comfortable. Bath shower drained poorly. Too expensive for a 2 star property."
United States
Chris
The price is €259
includes taxes & fees
22 Nov - 23 Nov
Hideaway Cottages
A hot tub, wooden deck, outdoor seating, and a staircase leading to a wooden cabin.

15. Sonoma Gem! Modern. Serene. Wine Retreat w/ HOT TUB!

Sonoma Gem! Modern. Serene. Wine Retreat w/ HOT TUB!
Verano
10.0 out of 10, Exceptional, (16 reviews)
"This is a perfect place for a family to stay."
United States
Nachyun
Sonoma Gem! Modern. Serene. Wine Retreat w/ HOT TUB!
A dining table set for a meal with wine glasses, plates, and a vase of flowers.

16. Romantic Wine Country Retreat with Hot Tub

Romantic Wine Country Retreat with Hot Tub
Boyes Hot Springs
9.8 out of 10, Exceptional, (55 reviews)
"Nice cozy spot. Small but clean. Great location. Hot tub is nice. Recommend."
United States
James D.
The price is €290
includes taxes & fees
25 Nov - 26 Nov
Romantic Wine Country Retreat with Hot Tub
Living area

17. 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 €328
includes taxes & fees
14 Dec - 15 Dec
2 bed I Silverado Resort & Spa in Napa - Wine Town
A hot tub on a wooden deck with string lights, outdoor furniture, and a barbecue grill.

18. The Harvard House: Napa, Hot Tub + Detached Studio

The Harvard House: Napa, Hot Tub + Detached Studio
Napa
9.4 out of 10, Exceptional, (56 reviews)
"It was easy to find the house, the bushes hide the driveway, would suggest trimming the height. The house was clean, except the garage where the washer and dryer were, cobwebs everywhere. The front bedroom bed, the top right kept falling down where my niece put her head! Over all it is a very nice house and easy access to every where."
United States
Katrina M
The price is €1,167
includes taxes & fees
15 Nov - 16 Nov
The Harvard House: Napa, Hot Tub + Detached Studio
A patio area with outdoor furniture, a pergola with string lights, and a stone fireplace.

19. 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 €297
includes taxes & fees
15 Nov - 16 Nov
Cottage at Main Street Farmhouse!
A backyard with a swimming pool and hot tub, surrounded by outdoor furniture and plants.

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

Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
Boyes Hot Springs
9.8 out of 10, Exceptional, (219 reviews)
"Perfect stay with a great host!"
United States
Anonymous traveller
The price is €689
includes taxes & fees
18 Nov - 19 Nov
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
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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Find holiday rentals that suit your style

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Top Oakville Hotel Reviews

An outdoor patio area with stone walls, tables, and chairs, and a pizzeria visible through the windows.
North Block Hotel

North Block Hotel

North Block Hotel
Yountville

10/10 Excellent

Wonderful service, great location
Ireland
Pragnesh
Reviewed June 17, 2018
North Block Hotel

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 €136 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.