Oakville Vacation Rentals from CA $41: Short-Term Rentals for 2026

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Our top choices for Oakville vacation rentals

A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

1. RiverPointe Napa Valley Resort

Stonehouse

Waldemar.

CA $208 total

includes taxes & fees

Nov 9 - Nov 10

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

2. The Napa Residences

Napa

David

CA $651 total

includes taxes & fees

Nov 17 - Nov 18

3. Silverado Napa Luxury 1 Bed Jr. Suite

Napa

Shayna

CA $297 total

includes taxes & fees

Nov 17 - Nov 18

A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

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

Kenwood

Samantha S.

CA $728 total

includes taxes & fees

Nov 9 - Nov 10

A residential area with a large house, a circular driveway, and a lawn.

5. Napa Condo Escape at Silverado

Napa

Josiah

CA $320 total

includes taxes & fees

Nov 17 - Nov 18

A large, white building with a symmetrical facade, surrounded by well-maintained lawns and palm trees.

6. 1 bed | 1 bath | Silverado Resort Experience

Napa

Patricia L.

CA $327 total

includes taxes & fees

Nov 17 - Nov 18

A spacious indoor area with a patterned floor, wooden staircase, and large windows offering a view of the outdoors.

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

Napa

Jason H.

CA $589 total

includes taxes & fees

Nov 10 - Nov 11

A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

8. Glen Ellen Retreats Coastal Cottage

Glen Ellen

Amanda D.

CA $766 total

includes taxes & fees

Nov 17 - Nov 18

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.

9. Napa relaxation at its finest at Silverado Resort

Napa

Jennifer C.

CA $410 total

includes taxes & fees

Dec 1 - Dec 2

10. Loft Studio w/ Private Balcony and Steam Bath in Downtown St. Helena

Downtown St. Helena

Cheryl Z.

CA $773 total

includes taxes & fees

Nov 8 - Nov 9

A residential area with detached houses, a central circular driveway, and a parking lot.

11. Silverado Napa Luxury 1 Bedroom

Napa

Kimberly

CA $328 total

includes taxes & fees

Nov 17 - Nov 18

A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

12. Glen Ellen Retreats Sunset Cottage

Glen Ellen

patrick s.

CA $760 total

includes taxes & fees

Nov 8 - Nov 9

A wooden deck with potted plants, a bench, and a building with large windows and a door.

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

Glen Ellen

Robert K.

CA $768 total

includes taxes & fees

Nov 19 - Nov 20

14. 2 bed I Silverado Resort & Spa in Napa - Wine Town

Napa

Jack K.

CA $448 total

includes taxes & fees

Nov 30 - Dec 1

A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

15. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen

Amy

CA $808 total

includes taxes & fees

Nov 8 - Nov 9

A patio area with outdoor furniture, a pergola with string lights, and a stone fireplace.

16. Cottage at Main Street Farmhouse!

McPherson

Lori

CA $440 total

includes taxes & fees

Nov 10 - Nov 11

17. 1 bed 1 bath Silverado Resort Experience Jr. Suite Condo

Napa

Ann B.

CA $296 total

includes taxes & fees

Nov 17 - Nov 18

A pool with a wooden deck and lounge chairs, surrounded by lush greenery and a mountainous backdrop.

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

Glen Ellen

Garrett B.

CA $1,417 total

includes taxes & fees

Nov 8 - Nov 9

A stone pathway leading to a house with a large window and a well-maintained garden.

19. North Napa Short Term Rental

Napa

Andy

CA $1,012 total

includes taxes & fees

Nov 15 - Nov 16

A room with a round table and chairs, a white door, and two framed artworks on the wall.

20. Poolside Retreat | Patio | 10 Min to DT

Napa

Stephen G.

CA $544 total

includes taxes & fees

Nov 9 - Nov 10

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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

St. Helena

10/10 Excellent

Grant

Napa Winery Inn

Napa

10/10 Excellent

Very friendly staff, clean rooms. Pool was nice but small area for lounging. Noisy right beside highway when at the pool but our room was on the other side of the hotel and no road noise could be heard from our room. The fridge was our only complaint! Couldn't hold more than 1 bottle of wine and was useless at holding any snacks. There was two small drawers for belongings and some hangers, but there wasn't a lot of storage for two people's clothes etc for 4 nights. Few gluten free breakfast...

Marci

A garden pathway leading to a building with a white picket fence and hanging purple flowers.

Glen Ellen Inn

Glen Ellen

10/10 Excellent

WONDERFUL! This Inn is a little gem. We stayed in the cottages and it was quaint, very pretty, treats left snd extremely comfortable. Our room had a refrigerator, jetted tub and a steam shower which was wonderful after a brisk walk around the town. We can’t wait to go back (we were there in Jan) to spend even more time enjoying the property and patio. Wonderful communications and the easiest checkin and out ever! 10/10 for sure!

Roxanne

A room with wicker furniture, a glass table, and a view of a lush garden.

Southbridge Napa Valley

Downtown St. Helena

10/10 Excellent

Tracey

A patio with two rocking chairs and a small table, surrounded by lush greenery and a fire feature.

Hilton Garden Inn Napa

Linda Vista

10/10 Excellent

Brendan

A stone patio with outdoor seating and string lights.

Olea Hotel

Glen Ellen

10/10 Excellent

Jonathan

A modern bedroom with a bed, a desk, and a large mirror.

GoodSpring Motel

Pueblo Park

10/10 Excellent

Jennifer

A building with a porch, wooden benches, and a brick wall.

The Jack London Lodge

Glen Ellen

10/10 Excellent

Barbara

A modern hotel room with a large bed, two chairs, a small table with a bottle and glasses, and a ceiling fan.

Gaige House

Glen Ellen

10/10 Excellent

brian

A covered outdoor seating area with red walls, wooden flooring, and string lights.

Napa Valley Railway Inn

Yountville

10/10 Excellent

Kelly

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakville vacation rentals we have selected for you start as low as CA $41 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 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.

Oakville Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakville vacation rentals

1. RiverPointe Napa Valley Resort

2. The Napa Residences

3. Silverado Napa Luxury 1 Bed Jr. Suite

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

5. Napa Condo Escape at Silverado

6. 1 bed | 1 bath | Silverado Resort Experience

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

8. Glen Ellen Retreats Coastal Cottage

9. Napa relaxation at its finest at Silverado Resort

10. Loft Studio w/ Private Balcony and Steam Bath in Downtown St. Helena

11. Silverado Napa Luxury 1 Bedroom

12. Glen Ellen Retreats Sunset Cottage

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

14. 2 bed I Silverado Resort & Spa in Napa - Wine Town

15. Glen Ellen Retreats Hot Tub Cottage

16. Cottage at Main Street Farmhouse!

17. 1 bed 1 bath Silverado Resort Experience Jr. Suite Condo

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

19. North Napa Short Term Rental

20. Poolside Retreat | Patio | 10 Min to DT

Find vacation rentals that suit your style

Top Oakville Hotel Reviews

Rancho Caymus Inn

10/10 Excellent

Find out more about Oakville

Oakville vacation rentals: An excellent choice for every season

How to find incredible deals on Oakville rentals

Frequently Asked Questions

Can I find a vacation rental in Oakville?

What are some of the best vacation home rentals in Oakville?

What can I see and do in Oakville?

What are vacation rentals like in Oakville?