Holiday rentals in Oakville

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Top-rated holiday rentals in Oakville

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest house in Glen Ellen

4.91 out of 5 average rating, 930 reviews

Crow Cottage ~ 3 min walk to town - restaurants

Crow Cottage is newly rebuilt and decorated in an eclectic whimsical style by the artist owners. It is light and airy with a private shade deck and sunny patio. The Cottage has a queen bed. There is a portable A/C. The cottage is well insulated so it doesn't get too hot in the summer. There is also a fan. Set on a country lane just a 3 min walk to great restaurants & a gourmet market. While we do have rescued cats in our yard we don't let them in any of the rooms. If highly allergic, reconsider.

12–19 Aug

£125 per night
Guest favourite

Apartment in Napa

4.99 out of 5 average rating, 147 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

8–15 Jun

£400 per night
Guest favourite

Guest suite in Sonoma

4.91 out of 5 average rating, 342 reviews

Wildwood Retreat and Pool

The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

15–22 Oct

£134 per night

Popular amenities for Oakville holiday rentals

Stay near Oakville's top sights

Oakville Grocery39 locals recommend
Robert Mondavi Winery23 locals recommend
Nickel & Nickel8 locals recommend

Other great holiday rentals in Oakville

Guest favourite

Apartment in Napa

4.99 out of 5 average rating, 318 reviews

Silverado Resort! Large 1BR Mountain View, Balcony

11–18 Jul

£300 per night
Guest favourite

Guest suite in Napa

4.94 out of 5 average rating, 137 reviews

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa

25 Jul – 1 Aug

£255 per night
Guest favourite

Apartment in Napa

4.96 out of 5 average rating, 107 reviews

Condo on PGA Silverado Course 15 min to BottleRock

12–19 Sept

£449 per night
Guest favourite

Guest suite in Napa

4.97 out of 5 average rating, 154 reviews

Luxury Private Poolside Suite

11–18 Aug

£176 per night
Guest favourite

Home in Napa

4.99 out of 5 average rating, 228 reviews

Peaceful home in the heart of Napa Valley

26 Jan – 2 Feb

£983 per night
Guest favourite

Flat in Napa

4.87 out of 5 average rating, 229 reviews

Napa, Silverado Country Club Spotless 2 bd 2 ba

17–24 Aug

£388 per night
Guest favourite

Guest suite in Glen Ellen

4.96 out of 5 average rating, 186 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

6–13 Oct

£153 per night
Guest favourite

Home in Napa

4.88 out of 5 average rating, 99 reviews

w/ Hot Tub & Detached Office, Modern 3BR in Napa!

2–9 Aug

£771 per night
Guest favourite

Home in Napa

4.92 out of 5 average rating, 157 reviews

Casa Alta with Hot Tub near Oxbow Market!

9–16 Feb

£477 per night
Guest favourite

Apartment in Napa

4.95 out of 5 average rating, 58 reviews

*Studio for Two at Silverado

Guest favourite

Guest house in Napa

4.97 out of 5 average rating, 75 reviews

*Minutes to Downtown ~ Napa Guest House*

5–12 May

£266 per night
Guest favourite

Home in Napa

4.97 out of 5 average rating, 33 reviews

Resort Living: Easy Access to Napa's Attractions

6–13 Jun

£443 per night

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