Search Winery Hotels in Oakville

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check availability on Oakville Winery Hotels

Our top choices for Oakville hotels with winery

The Casablanca Hotel

The Casablanca Hotel
3.5 star property
Grimsby
7.8 out of 10, Good, (1,000 reviews)
"The room was great for our overnight stay, comfortable beds, clean."
Canada
Lisa
The price is £75
includes taxes & fees
18 May - 19 May
The Casablanca Hotel

Comfort & Quiet Private Basement Unit

Comfort & Quiet Private Basement Unit
Milton
The price is £135
includes taxes & fees
18 May - 19 May
Comfort & Quiet Private Basement Unit

Hyatt Place Toronto/Mississauga Centre

Hyatt Place Toronto/Mississauga Centre
3.5 star property
Gateway
9.0 out of 10, Wonderful, (1,322 reviews)
"I recommend this place for staying!"
United States
Huda
The price is £95
includes taxes & fees
25 May - 26 May
Hyatt Place Toronto/Mississauga Centre

crestwoodmotel

crestwoodmotel
2.5 star property
Aldershot
6.8 out of 10, (21 reviews)
"Close to shopping and restaurants "
Canada
John
The price is £68
includes taxes & fees
18 May - 19 May
crestwoodmotel

Guesthouse Hideaway in Caledon

Guesthouse Hideaway in Caledon
Mayfield West
The price is £407
includes taxes & fees
17 May - 18 May
Guesthouse Hideaway in Caledon

The best of Ancaster, a cottage on 8 acres with river and trails and waterfalls

The best of Ancaster, a cottage on 8 acres with river and trails and waterfalls
Hamilton
The price is £541
includes taxes & fees
18 May - 19 May
The best of Ancaster, a cottage on 8 acres with river and trails and waterfalls
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.

Top Oakville Hotel Reviews

Frequently asked questions

How much does a winery hotel in Oakville cost?
Enjoy staying in a winery hotel in Oakville, with plenty of hotels from £68 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during the weekend or around public holidays.
Which area of Oakville is best to stay in for vineyards and wineries?
The picturesque area of Oakville, Ontario, is renowned for its stunning vineyards and charming wineries, making it a delightful choice for travellers seeking a taste of the region's rich wine culture. The scenic countryside is dotted with family-owned estates and boutique wineries, each offering unique tastings and tours that highlight the local terroir. The nearby Niagara Escarpment, with its breathtaking landscapes, enhances the experience, providing a beautiful backdrop for wine enthusiasts.

For couples wishing to enjoy a romantic getaway, the area around Bronte Creek is particularly enchanting. With its serene parks and lovely picnic spots, it invites leisurely afternoons spent sipping wine under the trees. Many wineries in this area also host intimate events, such as sunset tastings and vineyard dinners, great for creating lasting memories together.

Families will appreciate the Oakville area for its combination of wine experiences and outdoor activities. Some wineries offer family-friendly tours and events where children can explore the grounds while parents enjoy a tasting. The nearby parks and trails ensure there's plenty of space for kids to run around, making it an enjoyable outing for everyone.
What winery activities should we do in Oakville?
Oakville, Ontario, is a delightful destination for wine enthusiasts seeking a blend of scenic beauty and exceptional winery experiences. Nestled in the heart of Ontario's wine country, this charming town offers a wealth of opportunities to explore award-winning vineyards and indulge in tastings of exquisite local wines. The picturesque landscapes, complete with rolling hills and lush vineyards, create a stunning backdrop for your adventures.

For couples planning a romantic escape, visiting the renowned Vineland Estates Winery is a must. Here, you can savour a selection of premium wines while enjoying a gourmet meal at their exquisite restaurant, all set against a breathtaking vineyard view. The intimate atmosphere invites leisurely afternoons spent sipping wine and enjoying each other's company.

Families will find plenty to enjoy at the family-friendly Peller Estates Winery, where kids are welcome to join in the fun. The winery offers a variety of activities, including vineyard tours and interactive grape juice tastings for younger guests. With spacious picnic areas and beautiful gardens, it's the superb spot for a relaxed family outing.

Adventurous groups might consider signing up for a guided bike tour through the stunning Niagara wine region. This fun activity combines the thrill of cycling with the chance to explore multiple wineries in a single day, allowing you to taste a range of wines while soaking up the natural beauty of the area.
Does Oakville host any wine festivals or events?
Oakville, Ontario, is a hidden gem for wine enthusiasts, offering a delightful array of wine festivals and events throughout the year. The Oakville Festivals of Film and Art (OFFA) often features local wineries, showcasing their exceptional wines alongside captivating films and art displays. Moreover, the Oakville Wine Festival typically takes place in late summer, attracting both locals and visitors to sample a variety of wines from the Niagara region and beyond, all while enjoying live music and gourmet food pairings.

For couples seeking a romantic escape, the charming wineries in the nearby Niagara Peninsula provide an idyllic day trip. Picture yourself strolling through vineyards, indulging in wine tastings, and enjoying picturesque landscapes together. Many wineries also offer exclusive tours and intimate dining experiences, superb for creating lasting memories.

Families will find the Oakville area equally inviting, with events that cater to all ages. The Oakville Harvest Festival often includes activities for children, such as face painting and crafts, alongside wine tastings for the adults. This blend of fun and relaxation ensures that everyone can enjoy the local culture together.
How can I save on a winery hotel in Oakville with Expedia?
Members always get our best prices. Find our best Oakville hotel deals by joining One Key™, Expedia's free travel rewards programme. As a member, you can unlock instant savings and member perks when you're logged in to your account. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Is it cheaper to book flights and a winery hotel in Oakville as a package deal?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my winery hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel winery hotel in Oakville for you.

Explore a world of travel with Expedia