Oakville Holiday Rentals

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Check prices for these dates

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Oakville

Exterior
RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1347)
"A great place to stay"
United States
Debra
The price is HK$938
HK$1,303 total
includes taxes & fees
21 Dec - 22 Dec
RiverPointe Napa Valley Resort
Restaurant
The Napa Residences

The Napa Residences

5.0 star property
Napa
8.4 out of 10, Very good, (6)
"Very responsive, easy to check in and beautiful view of the golf course. We enjoyed our stay!"
United States
Thomas
The price is HK$277
HK$3,707 total
includes taxes & fees
9 Dec - 10 Dec
The Napa Residences
Outdoor pool, a heated pool
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

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

Glen Ellen
9.8 out of 10, Exceptional, (92)
"Fabulous location perched on the mountaintop. Home is modern and clean and has everything we needed to cook and enjoy our stay. Could not have been better! "
United States
Courtney S.
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley
Fridge, microwave, oven, stovetop
Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate

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

Shurtleff
10.0 out of 10, Exceptional, (11)
"The place was perfect! Lovely rooms, great amenities, and Daniel was very accommodating to our group. Our group was fairly big and the place was a good size for us to make use of the kitchen and common spaces."
United States
Lauren
The price is HK$4,360
HK$9,201 total
includes taxes & fees
31 Dec - 1 Jan 2026
Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate
Outdoor dining
VINEYARD VIEW HOT TUB PERFECT LOCATION FOR WINE TASTING AND GREAT RESTAURANTS

VINEYARD VIEW HOT TUB PERFECT LOCATION FOR WINE TASTING AND GREAT RESTAURANTS

Napa
9.8 out of 10, Exceptional, (396)
"Beautiful view, centrally located and great usable space"
United States
Jerry C.
VINEYARD VIEW HOT TUB PERFECT LOCATION FOR WINE TASTING AND GREAT RESTAURANTS
Interior
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

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

St Helena
10.0 out of 10, Exceptional, (252)
"Wonderful home, perfect place for a family of all ages! "
United States
Anonymous traveller
The price is HK$12,062
HK$15,459 total
includes taxes & fees
7 Dec - 8 Dec
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Outdoor dining
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

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

Kenwood
10.0 out of 10, Exceptional, (243)
"Absolutely beautiful and fun getaway with family and friends. We can't wait to come back next year. "
United States
Judy W.
The price is HK$12,453
HK$18,912 total
includes taxes & fees
29 Dec - 30 Dec
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Property grounds
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat

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

Napa
9.8 out of 10, Exceptional, (211)
"Very spacious property with very responsive hosts! "
United States
Jessica F.
Beautiful Napa Valley Home on Golf Course - Perfect Wine Country Retreat
Outdoor dining
Casa Bella Estate in Wine Country w/ New Pool!

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood
9.6 out of 10, Exceptional, (136)
"Lovely property. Pool was perfect for families with small children. Outdoor amenities are first rate. Comfortable bedding, well-equipped kitchen. Perfect setting for a large family gathering."
United States
Nita R.
Casa Bella Estate in Wine Country w/ New Pool!
Outdoor dining
The Corner Cottage ~ Downtown out your door with Private Vineyard

The Corner Cottage ~ Downtown out your door with Private Vineyard

Downtown Napa
10.0 out of 10, Exceptional, (238)
"We became fast friends with Susan the host who lives next door. She welcomed us with a bottle of wine. She gave us suggestions for places to go. The rooms were comfy and we had everything we needed. Highly recommend. "
United States
Philip S.
The Corner Cottage ~ Downtown out your door with Private Vineyard
Outdoor pool
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA

Private Sonoma Sanctuary 6 bed retreat with POOL and SPA

Boyes Hot Springs
9.8 out of 10, Exceptional, (118)
"Incredibly responsive and beautiful backyard! "
United States
Tina & Danny Mathan
The price is HK$6,226
HK$10,809 total
includes taxes & fees
2 Jan - 3 Jan 2026
Private Sonoma Sanctuary 6 bed retreat with POOL and SPA
Outdoor dining
Historic Cuneo Cottage Downtown Sonoma

Historic Cuneo Cottage Downtown Sonoma

Sonoma
9.4 out of 10, Exceptional, (92)
"Great location, huge backyard with lots of seating options!"
United States
Adrienne B.
The price is HK$2,365
HK$4,802 total
includes taxes & fees
6 Dec - 7 Dec
Historic Cuneo Cottage Downtown Sonoma
Private kitchen
Valley Bungalow

Valley Bungalow

Beard
9.8 out of 10, Exceptional, (68)
"Wonderful stay, very comfortable house, great location. Would stay again!"
United States
Stewart C.
Valley Bungalow
Games room
Beautiful Renovated House in the Heart of Napa 6 beds 4 bedrooms 2 bathrooms

Beautiful Renovated House in the Heart of Napa 6 beds 4 bedrooms 2 bathrooms

Central Napa
10.0 out of 10, Exceptional, (5)
"We loved the space, modern design, cleanliness, and EV charger. Plus the hot tub was very relaxing, and host even left us some wine to drink. When in Napa...."
United States
David L.
The price is HK$6,556
HK$9,575 total
includes taxes & fees
7 Dec - 8 Dec
Beautiful Renovated House in the Heart of Napa 6 beds 4 bedrooms 2 bathrooms
Outdoor dining
Luxury Sonoma Estate + Guest Cottage in Heart of Wine Country

Luxury Sonoma Estate + Guest Cottage in Heart of Wine Country

Sonoma
9.8 out of 10, Exceptional, (9)
"The property was beautiful and spacious for all 7 of us. It was in a nice location. Not too far from town. We loved the outdoors. It was a great house."
United States
Ashley P.
Luxury Sonoma Estate + Guest Cottage in Heart of Wine Country
Outdoor dining
Beautiful Home in Northwest Napa

Beautiful Home in Northwest Napa

Napa
9.8 out of 10, Exceptional, (53)
"Great location for the area. Kitchen well equipped. Host very responsive. Will stay again "
United States
Debbie S.
Beautiful Home in Northwest Napa
Terrace/patio
Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga

Calistoga
9.6 out of 10, Exceptional, (30)
"Great place! Clean, and very close to everything!"
United States
Levi J.
The price is HK$2,140
HK$2,815 total
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Wine County in your independant Cottage in Downtown Calistoga
Outdoor dining
Serene Napa Retreat Home!

Serene Napa Retreat Home!

Shurtleff
Serene Napa Retreat Home!
Fridge, microwave, oven, stovetop
Spacious Home Near Downtown Napa

Spacious Home Near Downtown Napa

Browns Valley
9.8 out of 10, Exceptional, (121)
"Beautiful spacious house comfortable beds wonderful stay"
United States
Chrissie G.
Spacious Home Near Downtown Napa
Exterior
Luxury Napa Estate With Pool/Hot-tub/Concierge

Luxury Napa Estate With Pool/Hot-tub/Concierge

Calistoga
10.0 out of 10, Exceptional, (50)
"Perfect location for a wine weekend. "
United States
John W.
The price is HK$10,214
HK$16,908 total
includes taxes & fees
8 Dec - 9 Dec
Luxury Napa Estate With Pool/Hot-tub/Concierge
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

SENZA Hotel

SENZA Hotel

10/10 Excellent
"Maybe another healthy breakfast option. Hot tub was good. "
David 2-night trip
Posted 2 days ago
SENZA Hotel

Find out more about Oakville

Search for holiday rentals in Oakville on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakville using one of the methods below:

  • View our selection of featured holiday rentals in Oakville
  • Use the map to find apartments and other holiday homes in the Oakville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakville while they last

Look no further and take a look at our great range of rental properties in Oakville!

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?

Luxury Retreat in Napa Valley – Two Stunning Homes on a Private Gated Estate: This holiday home rental outside of Oakville offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 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 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.