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Top Holiday Rentals in Oakville

RiverPointe Napa Valley Resort

3.0 star property
8.8 out of 10, Excellent, (1305)
"The trail nearby along the river was nice. "
The price is £114
includes taxes & fees
1 Sept - 2 Sept
RiverPointe Napa Valley Resort

As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

9.8 out of 10, Exceptional, (89)
"The house was phenomenal and we truly enjoyed our stay. The bedrooms all have large beds and bathrooms and are separate which provided nice privacy. The hot tub, common areas, and view were all amazing."
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

Historic Cuneo Cottage Downtown Sonoma

9.4 out of 10, Exceptional, (85)
"We enjoyed staying in your Cuneo Cottage. Loved the history and pictures throughout the house and the proximity to the Plaza, hiking trail and Sebastiani Winery!! "
The price is £565
includes taxes & fees
6 Sept - 7 Sept
Historic Cuneo Cottage Downtown Sonoma

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (130)
"Great place to celebrate family members birthdays and Mother’s Day. Excellent location in Sonoma County close to wineries and easy access to SFO and Santa Rosa Airports. Walking distance to a great coffee shop and two wine tasting rooms. Nice large fenced area with pool, jacuzzi, outdoor grill and gathering area. We also enjoyed the covered front porch for relaxing and enjoying the outdoors."
The price is £3,158
includes taxes & fees
20 Sept - 21 Sept
Casa Bella Estate in Wine Country w/ New Pool!

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (65)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Private Sonoma Sanctuary 6 bed retreat with POOL and SPA

9.8 out of 10, Exceptional, (106)
"Great stay from start to finish. We booked this for a trip with friends to celebrate my husband's 50th birthday. Communication with Tom was great. Was able to checkin a little early and allowed us to have ballons delivered before our arrival for a surpise for my husband. Plenty of space for 11 adults. Overall a great time."
The price is £1,146
includes taxes & fees
22 Sept - 23 Sept
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA

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

9.8 out of 10, Exceptional, (190)
"Comfortable and easy flow of kitchen, living and dining areas. Close to wineries and Sonoma Square."
The price is £654
includes taxes & fees
23 Sept - 24 Sept
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate

10.0 out of 10, Exceptional, (9)
"The property was great for a decent sized group! Nicely located and provided excellent space and amenities."
The price is £1,165
includes taxes & fees
1 Sept - 2 Sept
Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate

When in Glen | Sonoma | Panoramic Views | 3bed / 3bath

10.0 out of 10, Exceptional, (10)
"Beautiful homeSpacious Well appointedVery comfortable beds"
The price is £631
includes taxes & fees
3 Sept - 4 Sept
When in Glen | Sonoma | Panoramic Views | 3bed / 3bath

Charm and Modern Luxury in Heart of Wine Country

10.0 out of 10, Exceptional, (138)
"We had a great time, place was definitely roomy for the four of us. Great kitchen to cook in."
Charm and Modern Luxury in Heart of Wine Country

Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

9.8 out of 10, Exceptional, (202)
"Stunning home on a beautiful property. "
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (22)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is £307
includes taxes & fees
2 Sept - 3 Sept
Escape to Wine County in your independant Cottage in Downtown Calistoga

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (240)
"Wonderful accommodations for a family weekend in the wine country!"
The price is £1,712
includes taxes & fees
31 Aug - 1 Sept
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!

10.0 out of 10, Exceptional, (82)
"Had a great time!"
Spectacular Stone Pool/Spa. Views to The Bay. Near Sonoma Plaza. Ambiance plus!

Downtown Napa Cottage- walking distance to City Center

9.8 out of 10, Exceptional, (129)
"Amazing downtown Napa cottage, host was responsive and thoughtful!"
The price is £426
includes taxes & fees
2 Sept - 3 Sept
Downtown Napa Cottage- walking distance to City Center

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (234)
"The property was stunning and made for the perfect stay! William was a wonderful host and was super quick to respond to my questions. Would highly recommend! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Luxury Napa Valley Estate Surrounded by Vineyards

9.8 out of 10, Exceptional, (33)
"We celebrated my husband's 55th birthday with close friends at Vine & Rose and it exceeded expectations. The rooms were all private and nicely appointed, the chef recommendation was superb, and the communication was easy and responsive. "
Luxury Napa Valley Estate Surrounded by Vineyards

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

2.0 star property
10.0 out of 10, Exceptional, (8)
"Beautiful property"
The price is £244
includes taxes & fees
1 Sept - 2 Sept
2 bed I Silverado Resort & Spa in Napa - Wine Town

Winepress Cozy Getaway

10.0 out of 10, Exceptional, (102)
"Awesome property! Will stay again and recommend to others!"
Winepress Cozy Getaway

Vineyard Views in the Heart of the Napa Valley

10.0 out of 10, Exceptional, (67)
"Wonderful home and location and great communication with the property owner."
The price is £545
includes taxes & fees
2 Sept - 3 Sept
Vineyard Views in the Heart of the Napa Valley
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

Find out more about Oakville

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 £114 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?

Historic Cuneo Cottage Downtown Sonoma: This holiday home rental outside of Oakville is situated in the city centre, and has a BBQ and cable TV to help you feel content during your stay.

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.