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

Oakville Vacation Rentals

Dates

November 2026

December 2026

Check prices for these dates

In two weeks

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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

Napa

David

$419 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

2. RiverPointe Napa Valley Resort

Stonehouse

Waldemar.

$137 nightly

Dec 10 - Dec 11

Total with taxes and fees

3. Silverado Napa Luxury 1 Bed Jr. Suite

Napa

Shayna

$205 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

4. Cozy Napa Escape Silverado Resort

Napa

Carla

$220 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

5. 1 bed | 1 bath | Silverado Resort Experience

Napa

Patricia L.

$228 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Kenwood

Samantha S.

$452 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Jennifer C.

$290 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

Napa

Ann B.

$206 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Napa

Jack K.

$286 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

10. Glen Ellen Retreats Coastal Cottage

Glen Ellen

Amanda D.

$489 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Napa

Jason H.

$405 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Glen Ellen

Steve M.

$485 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

Napa

Stephen G.

$339 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

14. Cottage at Main Street Farmhouse!

McPherson

Lori

$279 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

patrick s.

$489 nightly

Nov 10 - Nov 11

Total with taxes and fees

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!

Napa

Erin Y.

$397 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

Napa

Greg S.

$407 nightly

Nov 12 - Nov 13

Total with taxes and fees

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!

Glen Ellen

Robert K.

$453 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

Amy

$520 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Napa

Tracie T.

$380 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Find vacation rentals that suit your style

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

Christine

A directional signpost with multiple arrows pointing to various local businesses and services.

Napa Valley Lodge

Yountville

10/10 Excellent

This place was phenomenal! The rooms were very spacious and as immaculately kept as all the pools, fountains and grounds. The breakfast was beyond continental including unlimited mimosas to go with your fresh espressos. All the staff were extremely friendly, attentive but not intrusive. Every single employee i met inquired if i was finding everything satisfactory or if i had any needs. We even had a microwave brought to one of our rooms for our week long stay. I would absolutely recommend this...

Karen

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

North Block Hotel

Yountville

10/10 Excellent

Robi

A serene garden with a pond, wooden benches, and a stone pathway leading to a building with a balcony.

Harvest Inn

Thoman

10/10 Excellent

My wife and I checked in here on our Honeymoon and we’re immediately greeted by some of the nicest people we’ve met so far. Extremely helpful and nice and they also upgraded us on our Honeymoon to a wonderful room looking out at the Vineyard. The room was incredible, large and very scenic. We even had our own in room fireplace. The staff is absolutely amazing, and that extends to the Harvest Kitchen which is located near check in. The food service was wonderful, including their pre fix menus....

Michael

A building with large windows and a tree in front.

Wydown Hotel

Downtown St. Helena

10/10 Excellent

Diane

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

Southbridge Napa Valley

Downtown St. Helena

10/10 Excellent

Hoilun

A sunlit indoor seating area with tables and chairs, large windows, and a glass ceiling.

Hotel Indigo Napa Valley by IHG

Napa

10/10 Excellent

William

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

Glen Ellen Inn

Glen Ellen

10/10 Excellent

Just amazing. I had a pretty significant event in my life that really required me to get away and clear my head. After some searching, I came across the Glen Ellen Inn Secret Cottages, about an hour away from where I live. The photos looked nice, and the reviews were all excellent, to the point that it was hard to believe. But the jetted tub called to me! I am so glad that I did this. The cottages are these amazing little places to just unwind and to find some peace. Right by the river, and...

Hanson

A stone patio with outdoor seating and string lights.

Olea Hotel

Glen Ellen

10/10 Excellent

Anonymous traveler

A wooden table with a wine glass and cheese on it, a chair with a plaid blanket, and a view of a green fence and mountains in the background.

Sonoma Creek Inn

Boyes Hot Springs

10/10 Excellent

A balcony with a table and chairs, overlooking a pool and lush greenery.

Kenwood Inn and Spa

Kenwood

10/10 Excellent

Nestled amongst dozens of nearby vineyards, this picturesque inn provided all the comforts of an intimate b&b with the high end care of a boutique property. The grounds were serene and well kept with winding pathways covered by fragrant flowering trellises and sounds of bubbling fountains throughout. The amenities were well-catered. Cool waters upon check in and check out. Turndown service including chocolates, lit fireplace and a custom playlist on surround sound. The brunch included with the...

Anonymous traveler

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

GoodSpring Motel

Pueblo Park

10/10 Excellent

Colleen

An aerial view of a residential area with houses, a swimming pool, and vineyards.

SENZA Hotel

Napa

10/10 Excellent

Linda

A spacious lobby with a fireplace, chandeliers, and a high ceiling.

Elm House Inn

Central Napa

10/10 Excellent

My wife and I really enjoyed our stay at the Elm House. The staff was pleasant, the room was nice, the property was all we needed. We didn’t need to be downtown in Napa or Sonoma because we traveled all over the areas for a week. We went from the coast to the redwoods, small towns, canyon roads, to wineries all over. The breakfast at the Inn was nice too. The atmosphere at the Inn was calming and soothing. We didn’t spend a lot of our time at the Inn, but it was always nice to come back to the...

damien

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

Anonymous traveler

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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Things to do in Napa Valley
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