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

Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (43 reviews)
"Nice, great location."
United States
Juan
$495 nightly
The price is $569
Sep 27 - Sep 28
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, (1,501 reviews)
"Great place to stay"
United States
Waldemar.
$132 nightly
The price is $152
Sep 29 - Sep 30
Total with taxes and fees
RiverPointe Napa Valley Resort
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

3. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (173 reviews)
"Awesome place to stay! "
United States
Amanda D.
$468 nightly
The price is $517
Sep 29 - Sep 30
Total with taxes and fees
Glen Ellen Retreats Coastal Cottage
A courtyard with stone buildings, outdoor seating, and a central tree.

4. Romantic Wine Country Retreat with Hot Tub

Romantic Wine Country Retreat with Hot Tub
Boyes Hot Springs
9.8 out of 10, Exceptional, (54 reviews)
"This is just what you need for a getaway to enjoy the sights and tastes of Sonoma and Napa. Our hosts were exceptional from start to finish and truly care about your experience at their quaint and spotless property. "
United States
Lisa G.
$267 nightly
The price is $295
Sep 29 - Sep 30
Total with taxes and fees
Romantic Wine Country Retreat with Hot Tub
A patio area with outdoor furniture, a pergola with string lights, and a stone fireplace.

5. Cottage at Main Street Farmhouse!

Cottage at Main Street Farmhouse!
McPherson
10.0 out of 10, Exceptional, (97 reviews)
"Excellent location and cozy!"
United States
Lori
$337 nightly
The price is $381
Sep 30 - Oct 1
Total with taxes and fees
Cottage at Main Street Farmhouse!
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

6. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (96 reviews)
"The stay was very nice"
United States
ladonna A.
$491 nightly
The price is $543
Oct 20 - Oct 21
Total with taxes and fees
Glen Ellen Retreats Hot Tub Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

7. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (84 reviews)
"Lovely, clean home in great location. Beautiful back yard. Great host. We loved our stay and plan to return!"
United States
Michelle W.
$463 nightly
The price is $512
Oct 19 - Oct 20
Total with taxes and fees
Glen Ellen Retreats Sunset Cottage

8. Spacious Honeymoon Suite

Spacious Honeymoon Suite
Downtown St. Helena
10.0 out of 10, Exceptional, (23 reviews)
"Great location, clean, and quiet. We could walk to several great restaurants! "
United States
Cheryl Z.
$408 nightly
The price is $461
Oct 6 - Oct 7
Total with taxes and fees
Spacious Honeymoon Suite
A two-story house with a garage, a balcony, and a driveway.

9. King bedroom #1 Wine Country Gateway With BBQ+Billiards

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
$254 nightly
The price is $281
Sep 27 - Sep 28
Total with taxes and fees
King bedroom #1 Wine Country Gateway With BBQ+Billiards
An outdoor dining area with a central fountain, surrounded by trees and illuminated by chandeliers.

10. Luxe Golf View Condo | Prime Napa Location

Luxe Golf View Condo | Prime Napa Location
Napa County
8.4 out of 10, Very good, (47 reviews)
"Great space for our weekend stay. Beautiful views of the golf course."
United States
Dan & Laura R.
$526 nightly
The price is $632
Sep 27 - Sep 28
Total with taxes and fees
Luxe Golf View Condo | Prime Napa Location
A large, white building with a symmetrical facade, surrounded by well-maintained lawns and palm trees.

11. 1 bed | 1 bath | Silverado Resort Experience

1 bed | 1 bath | Silverado Resort Experience
Napa
10.0 out of 10, Exceptional, (21 reviews)
"Great location on the property and close to all the sites Napa has to offer. "
United States
Patricia L.
$265 nightly
The price is $265
Oct 13 - Oct 14
Total with taxes and fees
1 bed | 1 bath | Silverado Resort Experience
A large, white, two-story building with a symmetrical facade, surrounded by well-maintained lawns and palm trees.

12. Cozy Napa Escape Silverado Resort

Cozy Napa Escape Silverado Resort
Napa
9.6 out of 10, Exceptional, (15 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
$270 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
Cozy Napa Escape Silverado Resort
A terrace with wicker chairs overlooking a scenic valley.

13. The Moonlit Retreat + Casita,Bocce & Sunset Views!

The Moonlit Retreat + Casita,Bocce & Sunset Views!
Glen Ellen
9.2 out of 10, Wonderful, (17 reviews)
"My family met for a family wedding and we stayed at this wonderful property . It is a perfect distance to get away yet close enough for ease of conveyance to stores , restaurants etc . The hosts were very good communicators and made us feel totally comfortable . The place was spotlessly clean and very comfortable . Nature abounds with deer , big bunnies and birds galore . Great guest experience and we would definitely stay again when visiting the area."
United States
Alfie H.
$951 nightly
The price is $951
Oct 11 - Oct 12
Total with taxes and fees
The Moonlit Retreat + Casita,Bocce & Sunset Views!
A modern bedroom with a large bed, a desk, and a dining area.

14. 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, (97 reviews)
"Amazing host, beautiful property, great location to downtown Napa! "
United States
Connie G.
$323 nightly
The price is $354
Oct 12 - Oct 13
Total with taxes and fees
Luxe apartment close to wineries EZ walk downtown resturants and tasting rooms
A dining table with two wine glasses and a plate of bread.

15. Romantic Napa Escape Prime Location King Bed, Private Patio & Pool

Romantic Napa Escape Prime Location King Bed, Private Patio & Pool
3.0 star property
Napa
$656 nightly
The price is $754
Sep 30 - Oct 1
Total with taxes and fees
Romantic Napa Escape Prime Location King Bed, Private Patio & Pool
A swimming pool with a slide, a barbecue area, and a wooden deck.

16. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$235 nightly
The price is $265
Oct 4 - Oct 5
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
A spacious indoor area with a tiled floor, a staircase, and large windows offering a view of the outdoors.

17. Poolside Retreat | Patio | 10 Min to DT

Poolside Retreat | Patio | 10 Min to DT
Napa
10.0 out of 10, Exceptional, (31 reviews)
"Nice place. Easy to book, checkin and checkout."
United States
Stephen G.
$445 nightly
The price is $485
Oct 7 - Oct 8
Total with taxes and fees
Poolside Retreat | Patio | 10 Min to DT
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

18. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (79 reviews)
"Lovely vacation rental"
United States
suzanne g.
$373 nightly
The price is $395
Oct 1 - Oct 2
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA

19. 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, (16 reviews)
"We had a great weekend getaway! Great location to both downtown Napa and wineries. "
United States
Joy S.
$384 nightly
The price is $384
Oct 13 - Oct 14
Total with taxes and fees
2 bed I Silverado Resort & Spa in Napa - Wine Town
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.

20. 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.
$362 nightly
The price is $362
Oct 25 - Oct 26
Total with taxes and fees
Napa relaxation at its finest at Silverado Resort
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

Napa Winery Inn

Napa Winery Inn

10/10 Excellent
"Staff was very helpful and friendly; room was exceptionally clean and quiet!"
Vicki 1-night trip
Posted 4 hours ago
Napa Winery 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 $152 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.

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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.