Oakdale vacation rentals

We found 332 vacation rentals — enter your dates for availability

Nestled amidst breathtaking landscapes, Oakdale invites you to immerse yourself in its enchanting atmosphere, where serene lakes and stunning waterfalls create a natural paradise. Whether you're teeing off at Oakdale Golf or skiing the slopes at Dodge Ridge, adventure awaits at every turn. With charming neighborhoods that blend vibrant college energy and tranquil retreats, our cozy vacation rentals—spacious homes and inviting cottages—offer the perfect base for group travelers seeking comfort, convenience, and a home-like experience in this captivating destination.

Holiday rentals with weekly discounts - Oakdale

Showing deals for:Dec 25 - Jan 1

Kitchen
Exterior detail
Outdoor dining
Interior
Exceptional
(71 reviews)

Beautiful Modern Swiss Cottage in Athens, NY

Athens

13% off
$365
$2,558 for 7 nights
All fees included
Beautiful Modern Swiss Cottage in Athens, NY
Living room
Kitchen
Sleepy Hollow Lake
Dining room
Exceptional
(5 reviews)

Spacious Lake Community House near Hudson

Coxsackie

10% off
$613
$4,294 for 7 nights
All fees included
Spacious Lake Community House near Hudson
Double height, open kitchen and dining perfect for large vacation meals
Patio accessible from dining/kitchen
Pool
Walnut dining table seats ten
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

7% off
$625
$4,377 for 7 nights
All fees included
Designer Home with Panoramic Views near Hudson
Exterior
Private kitchen
Living area
Interior
Exceptional
(109 reviews)

1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails

Catskill

9% off
$108
$758 for 7 nights
All fees included
1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails
front view from front porch
Living Room
Bedroom 2, full bed
Eat-In Kitchen with seating for 4
Exceptional
(15 reviews)

Cozy Quiet 3BR Fox Cottage 10 min from downtown Hudson

Hudson

25% off
$114
$798 for 7 nights
All fees included
Cozy Quiet 3BR Fox Cottage 10 min from downtown Hudson
Open kitchen with south-facing windows
Front door of the guest suite
Pool is open June-Sept.
Backyard firepit
Exceptional
(17 reviews)

Le Soleil Suite - Pool, Mtn Views 10 Min To Hudson

Hudson

9% off
$257
$1,802 for 7 nights
All fees included
Le Soleil Suite - Pool, Mtn Views 10 Min To Hudson
Dining
Exterior
Exterior
Private kitchen
Wonderful
(7 reviews)

Elmhurst House/ Town-House - Gnd Floor - 3bd Catskill Mtn View

Leeds

8% off
$226
$1,579 for 7 nights
All fees included
Elmhurst House/ Town-House - Gnd Floor - 3bd Catskill Mtn View
Enjoy the view of kitchen activities while hanging out on the couch.
View of the cabin from the road. Sitting on just over an acre of land.
Living area
A clean, simple hallway that leads to the downstairs bedroom and bathroom.
Exceptional
(41 reviews)

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill

9% off
$355
$2,487 for 7 nights
All fees included
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Interior
Property grounds
Terrace/patio
Living area
Exceptional
(16 reviews)

BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN

Hudson

9% off
$449
$3,146 for 7 nights
All fees included
BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN
Exterior
Pool
Living area
Property grounds
Wonderful
(5 reviews)

Hudson NY’S Country Serenity Guest Suite.

Hudson

9% off
$239
$1,670 for 7 nights
All fees included
Hudson NY’S Country Serenity Guest Suite.

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Find out more about Oakdale

Why visit Oakdale

  • Outdoor Adventures: Enjoy a variety of activities in the beautiful natural surroundings, including hiking, fishing, and boating on serene lakes.
  • Historic Sites: Visit the Oakdale Museum and explore the rich history of the area through its fascinating exhibits.
  • Golfing: Play a round at local golf courses that offer stunning views and enjoyable challenges for golfers of all levels.
  • Charming Accommodations: Choose from cozy cottages and private vacation homes for a comfortable stay.
  • Nearby Attractions: Discover trendy dining and shopping experiences in nearby towns for a complete vacation experience.

Popular types of accommodation in Oakdale

If you're exploring vacation rental options in Oakdale, you're in for a treat. Our most popular accommodations include houses, cozy cottages, and modern apartments. Whether you're looking for spacious house rentals or charming condo rentals, Oakdale offers a variety of California vacation rentals to suit your needs. Discover the best vacation rentals that promise comfort and convenience for your getaway.

  • Houses: The top choice for visitors to Oakdale, these homes offer spacious comfort and a home-like atmosphere for families and groups.
  • Cottages: A delightful option for a quaint and cozy stay, perfect for couples or small families seeking a charming escape.
  • Apartments: Ideal for travelers looking for modern amenities and convenience, these rentals provide a city-like experience.
  • Cabins: A popular pick for those wanting a rustic feel, these cabins immerse you in nature's beauty.
  • Chalets: Offering a unique blend of comfort and style, chalets are great for those seeking a scenic retreat.**

Top attractions near Oakdale

Oakdale, Hudson, Columbia County, offers a picturesque setting for outdoor and romantic vacations. Explore historic sites, serene lakes, and the nearby national state park, perfect for cultural and family experiences. Don't miss out on local attractions like the Oakdale Museum, golf courses, and friendly vacation spots. For accommodation, consider the best vacation rentals to enhance your stay and make lasting memories in this charming destination.

  • Olana State Historic Site: A stunning blend of art and nature, this historic site features a magnificent Persian-inspired home and picturesque views of the Hudson Valley. Explore its beautiful grounds and learn about the life of painter Frederic Edwin Church.
  • Hudson Opera House: A vibrant cultural hub, this historic venue hosts a variety of performances and art exhibits. Enjoy the unique architecture and immerse yourself in the local arts scene just a short walk away.
  • Sleepy Hollow Lake: Perfect for outdoor enthusiasts, this serene lake offers beautiful scenery, a beach for relaxation, and romantic sunsets. Ideal for picnics, kayaking, or simply enjoying nature's beauty.

Things to do recommended for couples

For a romantic getaway in Oakdale, visit Hudson Chatham Winery for a cozy wine tasting just 8 miles away, or enjoy Tousey Winery, located 12 miles away, for a charming atmosphere. If you're in the mood for adventure, Catamount Ski Area, 16 miles away, offers thrilling slopes for couples.

Things to do recommended for families

During your family vacation in Oakdale, enjoy a day at Saugerties Village Beach for relaxation, skate at the nearby Kiwanis Ice Arena for some thrilling fun, or unwind at Mosher Park, where wellness meets nature. Each destination promises memorable experiences for everyone.

Things to do recommended for groups

Experience the charm of Oakdale by catching a show at the Max and Lillian Katzman Theater, exploring unique finds at Stoddard Corner, or enjoying a round of golf at the scenic Catskill Golf Club, perfect for outdoor enthusiasts in your group.

*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 Oakdale

When planning your trip—whether you're traveling with a group, family, pets, or looking for extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Oakdale with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Oakdale with young kids: Traveling with little ones can be a bit tough. It's important to prioritize their comfort and safety, along with amenities that suit their age, 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 Oakdale: For many families, a vacation isn't truly fulfilling without their furry companions. If you can relate to this, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakdale: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Oakdale

Oakdale, nestled in Hudson, Columbia County, offers a charming blend of outdoor adventures and scenic beauty, perfect for a romantic or family-friendly getaway. Explore its friendly atmosphere while enjoying historical sites and secluded spots ideal for relaxation. Nearby towns provide trendy dining and shopping experiences, making it a wonderful vacation destination. Whether you're seeking family fun or a peaceful retreat, Oakdale has something special for everyone.

  • Hudson: Hudson is a charming city that perfectly blends outdoor adventure with stunning scenery. Nestled near Oakdale, it's known for its vibrant arts scene and historic architecture. Visitors can explore the picturesque waterfront along the Hudson River, hike in the nearby mountains, or engage in thrilling activities at local ski resorts. With its diverse restaurants and boutique shops, Hudson offers a delightful urban experience while providing easy access to natural attractions like lakes and scenic picnic spots. Whether you're skiing in winter or hiking in summer, Hudson is a gateway to memorable outdoor experiences.
  • Catskill: Just a short drive from Oakdale, Catskill is an outdoor enthusiast's paradise. Renowned for its breathtaking landscapes, this city offers a plethora of activities for adventure seekers, including skiing, hiking, and exploring beautiful waterfalls. The majestic Catskill Mountains provide a stunning backdrop and are perfect for both winter sports and summer hikes. With its charming downtown area filled with local shops and eateries, Catskill is an ideal stop for those looking to enjoy both nature and community vibes. Don’t miss the chance to unwind by the serene lakes that dot the region.
  • Athens: Located just 2 miles from Oakdale, Athens is a picturesque city that offers a romantic escape for travelers. Known for its scenic waterfront and friendly atmosphere, visitors can explore beautiful lakes and enjoy beach activities during the warmer months. The nearby mountains provide ample opportunities for hiking and winter sports, making it a year-round destination. Athens also boasts a selection of quaint shops and delightful dining options, perfect for a cozy evening out. Whether you're taking a leisurely stroll along the river or enjoying a sunset on the beach, Athens offers a peaceful retreat with plenty of charm.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, booking a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is designed to help you plan your travels with ease, whether you're creating new trips, refining your plans, or reviewing your bookings. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Oakdale getaway

Learn about the unique charm of Oakdale with a stay in a private vacation home. 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 top things to see and do while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Oakdale a one-of-a-kind vacation spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Kaaterskill Falls (15 mi / 24.1 km)
  • Catskill Golf Club (5 mi / 8 km)
  • Hudson Chatham Winery (8.3 mi / 13.3 km)
  • Thunderhart Golf Course (13.5 mi / 21.8 km)
  • Village Books (14.8 mi / 23.9 km)

Exploring the natural features in Oakdale

Whether you're looking for adventure or just want to appreciate the scenery, Oakdale is a great place to get out in nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Sleepy Hollow Lake (3.4 mi / 5.4 km)
  • Art Omi International Arts Center - Fields Sculpture Park (8.1 mi / 13 km)
  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Copake Lake (12 mi / 19.4 km)
  • Clermont State Historic Site (14.2 mi / 22.8 km)
  • Kaaterskill Falls (15 mi / 24.1 km)

Traveling to and around Oakdale

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 4.6 mi (7.4 km) from the city center. If you can't find a flight that's convenient for your trip, 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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Oakdale, New York, the best area to stay is near the picturesque waterfront. This charming neighborhood offers a serene atmosphere, making it ideal for relaxation while still being close to local attractions. The scenic views along the Great South Bay are great for leisurely walks, and you can enjoy outdoor activities such as kayaking or boating.Another appealing aspect of this area is its proximity to the historic Oakdale Village, which features quaint shops and eateries that capture the local charm. Additionally, you'll find the beautiful Connetquot River State Park Preserve nearby, offering miles of trails for hiking and ample opportunities for birdwatching. While the exact number of properties can vary, the waterfront area generally has a nice selection of vacation rentals that cater to different preferences, ensuring you can find a great spot for your stay.
How much does it cost to rent a vacation home in Oakdale?
Prices for vacation 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 vacation 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 vacation rentals in Oakdale?
A long-stay vacation rental in Oakdale is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Oakdale vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oakdale with parking available—perfect for families or travelers 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 vacation rental?
Book your Oakdale vacation 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 vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakdale, New York, United States of America?
In Oakdale, visitors can enjoy a charming small-town atmosphere with several attractions nearby. One of the highlights is the Connetquot River State Park Preserve, which offers scenic walking trails, fishing opportunities, and a chance to explore the natural beauty of Long Island. The area is also known for its proximity to the Great South Bay, where travelers can find activities such as boating and kayaking.In addition, the Oakdale Village Center features quaint shops and local eateries, providing a taste of the local culture. For those interested in history, the nearby Long Island Maritime Museum in West Sayville offers insights into the region's nautical heritage.
Can I change or cancel my Oakdale home rental booking on Vrbo?
To find Oakdale vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, 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 organizing 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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