Oakville Vacation Rentals

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Check prices for these dates

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

Our top choices for Oakville vacation 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
$419 nightly
The price is $482
Nov 12 - Nov 13
Total with taxes and fees
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, (1,557 reviews)
"Great place to stay"
United States
Waldemar.
$137 nightly
The price is $158
Dec 10 - Dec 11
Total with taxes and fees
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
$205 nightly
The price is $205
Nov 12 - Nov 13
Total with taxes and fees
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
$220 nightly
The price is $220
Nov 16 - Nov 17
Total with taxes and fees
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.
$228 nightly
The price is $228
Nov 11 - Nov 12
Total with taxes and fees
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.
$452 nightly
The price is $512
Nov 10 - Nov 11
Total with taxes and fees
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.
$290 nightly
The price is $290
Nov 30 - Dec 1
Total with taxes and fees
Napa relaxation at its finest at Silverado Resort
Room

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.
$206 nightly
The price is $206
Nov 11 - Nov 12
Total with taxes and fees
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.
$286 nightly
The price is $286
Nov 10 - Nov 11
Total with taxes and fees
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.
$489 nightly
The price is $542
Nov 11 - Nov 12
Total with taxes and fees
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.
$405 nightly
The price is $441
Nov 10 - Nov 11
Total with taxes and fees
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 had a really pleasant stay here. Lots of personal touches and amenities provided which are very thoughtful. Nice location away from Sonoma and accessible to the more Northern areas of Sonoma County as well."
United States
Steve M.
$485 nightly
The price is $550
Nov 23 - Nov 24
Total with taxes and fees
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.
$339 nightly
The price is $367
Nov 10 - Nov 11
Total with taxes and fees
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
$279 nightly
The price is $319
Nov 10 - Nov 11
Total with taxes and fees
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.
$489 nightly
The price is $542
Nov 10 - Nov 11
Total with taxes and fees
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.
$397 nightly
The price is $424
Dec 1 - Dec 2
Total with taxes and fees
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.
$407 nightly
The price is $436
Nov 12 - Nov 13
Total with taxes and fees
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.
$453 nightly
The price is $504
Nov 19 - Nov 20
Total with taxes and fees
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
$520 nightly
The price is $576
Nov 10 - Nov 11
Total with taxes and fees
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.
$380 nightly
The price is $380
Nov 30 - Dec 1
Total with taxes and fees
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

A stone fireplace with a fire, outdoor seating with chairs and a table, and a sign reading "Rancho Cayman Inn".
Rancho Caymus Inn

Rancho Caymus Inn

Rancho Caymus Inn
St. Helena

10/10 Excellent

We absolutely loved the inn. The breakfast was wonderful and the staff was great and incredibly helpful. The facilities were clean and comfortable and extremely well-managed. Our needs were attended whenever we needed something or advice on where to go. The burritos across the street were also AMAZING! Can’t wait to stay here again on our next trip to the area.
United States
Christine
Reviewed August 4, 2025
Rancho Caymus Inn

Find out more about Oakville

Everything you need to know about Oakville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville vacation 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 vacation.

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 vacation rental in Oakville?

Yes, we have vacation rentals in Oakville close to Folie a Deux, or you can go with a more remote option if you're looking for extra privacy while you relax. 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 vacation home rentals in Oakville?

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella: This vacation home rental outside of Oakville is located in the mountains and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and a 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 vacation rentals like in Oakville?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Oakville. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips.

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