Oakdale holiday lettings

We found 302 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Oakdale to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include air conditioning and a pool. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Oakdale

Showing deals for:15 May - 22 May

Image gallery for Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY

Living area
8.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)

Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY

Athens

8% off
Price is £6,933
for 7 nights, 1 chalet
£990 per night
includes taxes & fees
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Oakdale getaway

Learn about the unique charm of Oakdale 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.

Sightseeing in and around Oakdale

Do you want to find things to do while you're in the area? Venture out of your holiday home and check out everything that Oakdale has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Thunderhart Golf Course (13.5 mi / 21.8 km)
  • Kaaterskill Falls (15 mi / 24.1 km)
  • Catskill Golf Club (5 mi / 8 km)
  • Hudson Chatham Winery (8.3 mi / 13.3 km)
  • Tousey Winery (11.6 mi / 18.7 km)

Exploring the natural features in Oakdale

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Oakdale is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Sleepy Hollow Lake (3.4 mi / 5.4 km)
  • Dutchman’s Landing (4.6 mi / 7.5 km)
  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Copake Lake (12 mi / 19.4 km)
  • Kaaterskill Falls (15 mi / 24.1 km)
  • Mull Island (15.2 mi / 24.4 km)

Travelling to and around Oakdale

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 4.6 mi (7.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Pittsfield, MA (PSF-Pittsfield Municipal), which is 27.7 mi (44.6 km) away.

Frequently asked questions

What is the best area to stay in Oakdale when booking a holiday rental?
When considering a holiday rental in Oakdale, New York, a popular area to stay is along the picturesque waterfront. This charming neighbourhood offers a relaxed atmosphere with stunning views of the Great South Bay. You'll find a selection of properties here, ranging from cosy cottages to more spacious homes, suiting various group sizes and preferences.

In this area, you can easily visit the captivating Connetquot River State Park Preserve, where outdoor enthusiasts can enjoy hiking, fishing, and birdwatching amidst beautiful natural surroundings. Additionally, the local marina provides opportunities for boating and water sports, making it an ideal spot for families and those looking to enjoy the great outdoors.

Another appealing aspect of staying in this part of Oakdale is its proximity to local dining options and shops, ensuring that you have everything you need for a comfortable stay.
How much does it cost to rent a holiday home in Oakdale?
Prices for holiday rentals in Oakdale 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakdale to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakdale holiday house rentals?
You can find great discounts on house rentals in Oakdale on Vrbo, 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 find long-stay holiday rentals in Oakdale?
A long-stay holiday rental in Oakdale 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Oakdale holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oakdale 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 on Vrbo 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.
How early should I book a Oakdale holiday rental?
Book your Oakdale holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakdale?
In Oakdale, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. One of the main draws is the picturesque Connetquot River State Park Preserve, which offers opportunities for hiking, fishing, and birdwatching. The park's scenic trails are superb for nature enthusiasts and families alike.

For those interested in local history, the Oakdale Historic Society provides insights into the area's past, often featuring events and exhibitions that showcase its heritage. The nearby Great South Bay is ideal for water activities, including kayaking and boating, and offers beautiful views, particularly at sunset.

The charming village atmosphere of Oakdale is complemented by local shops and eateries, where visitors can enjoy a taste of Long Island's culinary offerings.
Can I change or cancel my Oakdale home rental booking on Vrbo?
To find Oakdale holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oakdale holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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