Oakville holiday rentals

We found 42 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Oakville that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a fireplace. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Why visit Oakville

  • Scenic Urban Parks: Oakville boasts beautiful parks perfect for relaxation and outdoor activities, making it ideal for families and nature lovers alike.
  • Exciting Motor Racing Events: Experience thrilling motor racing events that showcase the adrenaline and excitement of the sport in a vibrant atmosphere.
  • Charming Local Streets: Stroll through quaint streets filled with unique shops and delightful eateries, reflecting the town's inviting charm.
  • Natural Beauty: Explore nearby state parks that offer stunning landscapes and opportunities for hiking and outdoor adventures.
  • Convenient Accommodation: Enjoy a range of holiday rentals, from cosy cottages to modern apartments, catering to various needs and preferences.

Popular types of accommodation in Oakville

Discover Oakville, Maryland, where delightful holiday rentals await. Enjoy charming private holiday homes, cosy cottages and modern apartments, many featuring additional parking options and wheelchair accessibility for utmost convenience. Explore local attractions, landmarks and authentic experiences right in the heart of Oakville, ensuring a truly memorable stay. Whether you choose an apartment home or an ideal house rental, Oakville offers transparency, savings and reassurance for every traveller.

  • Private Holiday Homes: Enjoy the luxury and exclusivity of a private residence, offering ample space and privacy for a perfect family retreat.
  • Cottages: Experience a charming rural escape in cosy cottages, ideal for a peaceful, countryside getaway.
  • Apartments: Opt for modern apartments providing convenient, stylish living spaces suited for urban explorers.
  • Cabins: Embrace a rustic charm in quaint cabins, perfect for those seeking a nature-infused holiday.
  • Chalets: Indulge in the cosy ambiance of traditional chalets, offering a warm, inviting atmosphere for a relaxed stay.**

Top attractions near Oakville

Oakville, Maryland, offers a delightful blend of outdoor and urban experiences. Families and city lovers alike can enjoy scenic urban parks, exhilarating motor racing events, and the natural beauty of national state parks. As a perfect destination for an active holiday, Oakville invites visitors to explore its varied attractions and create lasting memories amidst its vibrant city charm.

  • Maryland International Raceway: Experience thrilling motor racing, located 16km from Oakville, offering a mix of sport and adventure vibes.
  • Greenwell State Park: Enjoy scenic outdoor adventures at this national state park situated 11km from Oakville, perfect for nature enthusiasts.
  • Sotterley Plantation: Immerse yourself in culture at this historic house located 10km from Oakville, reflecting rich local heritage.

Things to do recommended for couples

Discover Oakville's charm with a romantic walk by the harbour and a cosy dinner at a quaint local bistro. Enjoy scenic views and intimate moments perfect for a couple's retreat.

Things to do recommended for families

Experience family fun in Oakville, Maryland with walks through scenic parks, engaging local museums, and interactive community events, ensuring a memorable holiday for every member of the family.

Things to do recommended for groups

Groups in Oakville can experience local excitement at Maryland International Raceway and Budds Motorcross Speedway, both situated 16km from the town, offering a blend of sport and adventure for an unforgettable outing.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Oakville

Whether you're travelling with a group, as a family, with your pets, or seeking longer stays, be sure to filter according to your priorities. Here are some Stayz booking tips for you.

  • Traveling to Oakville with a group: Consider how many bedrooms you'll require, along with facilities like a fully-equipped kitchen or an outdoor area suitable for a group gathering. Fortunately, you can refine your search for all these features, and more, on Stayz.
  • Traveling to Oakville with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oakville: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakville: If you're seeking holiday lets with special offers for month-long or extended stays, you've come to the right place. With the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also want to include options such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Oakville

Oakville in Maryland offers a delightful blend of family-friendly charm and outdoor adventures. Wander through its quaint streets, enjoy diverse shopping options, and explore local transport links that make exploring the village a breeze. The natural organic greenery and engaging urban excursions create a perfect setting for a memorable Oakville getaway that combines historical allure with modern urban vibes.

  • California: This vibrant city is situated 16km from Oakville and offers travellers a refreshing blend of outdoor excitement, scenic beauty and adventure. Visitors can enjoy the thrill of motor racing at the local racetrack, explore expansive recreational areas and discover educational venues, all set against dramatic cliffs and a picturesque bay backdrop. The unique combination of natural beauty and action-packed attractions makes California a compelling destination for those seeking both relaxation and adventure.
  • Hollywood: Located 6km from Oakville, Hollywood presents a delightful mix of outdoor pursuits, scenic vistas and adventurous activities. The city is well-known for its recreational areas, motor racing events and educational attractions. With landmarks such as a stunning bay, a sandy beach and impressive cliffs, Hollywood offers a charming experience that captures the essence of coastal allure and dynamic exploration.
  • Mechanicsville: As the heart of Oakville, Mechanicsville is renowned for its sporty and adventurous spirit. This city offers an array of outdoor activities from motor racing and golfing to exploring expansive recreational areas. Iconic landmarks like the racetrack, a bustling stadium and a serene lake provide an engaging backdrop for both leisurely pursuits and thrilling adventures, ensuring a memorable visit for all who venture here.

Booking with Stayz is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting to book a longer stay can often result in significant savings. To discover the ideal Stayz property that suits your budget, simply utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides a dedicated area where you can craft new journeys, continue your existing plans, or review and organise your reservations. Properties you have either saved or booked are neatly categorised into Potential, Upcoming, or Current Trips. For further exploration of the Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Oakville getaway

Learn about the unique charm of Oakville with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Oakville

Are you searching for top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Oakville a one-of-a-kind holiday spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (8.2 mi / 13.3 km)
  • Breton Bay Golf Course (8.5 mi / 13.7 km)
  • Maryland International Raceway (10.2 mi / 16.4 km)
  • Budds Creek Motocross Park (10.4 mi / 16.8 km)
  • Perigeaux Vineyards and Winery (7.6 mi / 12.2 km)
  • Wicomico Shores Golf Course (11.2 mi / 18.1 km)

Exploring the natural landscape of Oakville

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oakville is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Battle Creek Cypress Swamp Sanctuary (7.5 mi / 12 km)
  • St. Mary's River State Park (10.3 mi / 16.6 km)
  • Matoaka Beach (10.4 mi / 16.8 km)
  • Flag Ponds Nature Park (10.6 mi / 17 km)
  • St. Clement's Island State Park (13.4 mi / 21.6 km)
  • Cove Point Beach (13.9 mi / 22.4 km)

Frequently asked questions

What is the best area to stay in Oakville when booking a holiday rental?
When considering a holiday rental in Oakville, Maryland, the surrounding areas offer some delightful options that can enhance your stay. One of the most appealing neighbourhoods nearby is the picturesque town of Ellicott City. Known for its charming historic district, Ellicott City features cobblestone streets lined with unique shops, cafés, and restaurants. A visit to the B&O Railroad Museum is a must for history enthusiasts, while the scenic Patapsco Valley State Park offers beautiful hiking trails for outdoor lovers.Another fantastic area to consider is Columbia, which is also close to Oakville. Columbia is popular for its planned community design and vibrant cultural scene. It boasts numerous parks and recreational facilities, as well as the impressive Merriweather Post Pavilion, which hosts a variety of concerts and events throughout the year.
What are the top attractions in Oakville?
In Oakville, Maryland, visitors can enjoy a range of attractions that highlight the area's natural beauty and cultural significance. The nearby Patapsco Valley State Park offers numerous trails for hiking and cycling, allowing guests to immerse themselves in the lush landscapes and scenic views along the Patapsco River. This area is superb for outdoor enthusiasts seeking adventure amidst nature.For those interested in history, the historic Ellicott City is just a short drive away, featuring charming streets lined with shops, restaurants, and the fascinating B&O Railroad Museum, which showcases the region's rich rail history. The area is also known for its quaint architecture and vibrant community events.Additionally, the local area boasts various family-friendly parks and recreational facilities, providing ample opportunities for picnics, sports, and relaxation.
Are all fees included in the Oakville holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oakville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oakville holiday homes?
You can find great discounts on holiday homes in Oakville on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oakville holiday home booking on Stayz?
To find Oakville holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakville?
A long-stay holiday home in Oakville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakville holiday home?
Book your Oakville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakville?
Prices for holiday homes in Oakville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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