Oakdale holiday rentals

We found 333 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:18 Dec - 25 Dec

Front porch
Living area
Master suite balcony
Dining
Exceptional
(35 reviews)

Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away

Catskill

8% off
AU$4,966
for 7 nights, 1 cabin
AU$709 per night
includes taxes & fees
Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away
Interior
Exterior detail
Interior
Outdoor dining
Exceptional
(71 reviews)

Beautiful Modern Swiss Cottage in Athens, NY

Athens

12% off
AU$3,901
for 7 nights, 1 home
AU$557 per night
includes taxes & fees
Beautiful Modern Swiss Cottage in Athens, NY
Sleepy Hollow Lake
Kitchen
Dining room
Living room
Exceptional
(5 reviews)

Spacious Lake Community House near Hudson

Coxsackie

9% off
AU$5,075
for 7 nights, 1 home
AU$725 per night
includes taxes & fees
Spacious Lake Community House near Hudson
Terrace/patio
Interior
Private kitchen
Dining
Exceptional
(245 reviews)

Designers Own Year-Round Hudson Valley Getaway Cottage

Hudson

8% off
AU$2,511
for 7 nights, 1 cottage
AU$359 per night
includes taxes & fees
Designers Own Year-Round Hudson Valley Getaway Cottage
Walnut dining table seats ten
Patio accessible from dining/kitchen
Front Door entrance
Pool
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

8% off
AU$5,686
for 7 nights, 1 home
AU$812 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
view of cottage from the road and parking to the right
Private kitchen
Interior
Exterior
Exceptional
(109 reviews)

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

Catskill

8% off
AU$1,118
for 7 nights, 1 cottage
AU$160 per night
includes taxes & fees
1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails
front view from front porch
Living Room
Eat-In Kitchen with seating for 4
Smart TV, electric fireplace, games. (Guests use their own streaming services)
Exceptional
(15 reviews)

Cozy Quiet 3BR Fox Cottage 10 min from downtown Hudson

Hudson

23% off
AU$1,274
for 7 nights, 1 home
AU$182 per night
includes taxes & fees
Cozy Quiet 3BR Fox Cottage 10 min from downtown Hudson
Private access to the backyard, firepit, pool, BBQ and hamock.
Front door of the guest suite
Backyard firepit
Pool is open June-Sept.
Exceptional
(17 reviews)

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

Hudson

8% off
AU$2,583
for 7 nights, 1 home
AU$369 per night
includes taxes & fees
Le Soleil Suite - Pool, Mtn Views 10 Min To Hudson
Dining
Exterior
Private kitchen
Living area
Wonderful
(7 reviews)

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

Leeds

8% off
AU$2,342
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Elmhurst House/ Town-House - Gnd Floor - 3bd Catskill Mtn View
Living area
Pool
Interior
Property grounds
Wonderful
(5 reviews)

Hudson NY’S Country Serenity Guest Suite.

Hudson

8% off
AU$2,664
for 7 nights, 1 apartment
AU$381 per night
includes taxes & fees
Hudson NY’S Country Serenity Guest Suite.
A clean, simple hallway that leads to the downstairs bedroom and bathroom.
View of the cabin from the road. Sitting on just over an acre of land.
Entertainment meets comfort here. Enjoy a movie night on the big screen.
Enjoy the view of kitchen activities while hanging out on the couch.
Exceptional
(41 reviews)

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

Catskill

8% off
AU$2,979
for 7 nights, 1 cabin
AU$426 per night
includes taxes & fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Property grounds
Interior
Interior
Exceptional
(16 reviews)

BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN

Hudson

8% off
AU$4,955
for 7 nights, 1 apartment
AU$708 per night
includes taxes & fees
BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN
Interior
Interior
Private kitchen
Interior
Exceptional
(6 reviews)

Welcome to Casa Del Rio for the active traveler, the wonderer or family getaway.

Hudson

8% off
AU$5,618
for 7 nights, 1 home
AU$803 per night
includes taxes & fees
Welcome to Casa Del Rio for the active traveler, the wonderer or family getaway.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Oakdale

  • Historic charm: Oakdale boasts a rich cultural heritage with its historic sites and scenic walking paths.
  • Picturesque lakes and rivers: Enjoy serene lakes and rivers ideal for outdoor adventures and romantic getaways.
  • Local arts and culture: Experience vibrant arts centres and local craft scenes that highlight regional talent.
  • Family-friendly attractions: Revel in outdoor activities and scenic parks perfect for family excursions.
  • Cozy accommodation options: Choose from a variety of comfortable holiday homes and modern apartments.

Popular types of accommodation in Oakdale

Welcome to Oakdale, a charming city nestled in Hudson, Columbia County, New York. Known for its serene landscapes and friendly atmosphere, Oakdale offers delightful experiences amidst nature. Explore scenic parks, enjoy leisurely walks along the river, or indulge in local cuisine. When it comes to accommodation, you'll find an array of private holiday homes, cosy cottages, and modern apartments, perfect for a memorable getaway. Discover your ideal holiday rental in Oakdale and make your stay truly special.

  • Private Holiday Homes: The most sought-after option in Oakdale, offering spacious and personalised living for families or groups.
  • Cottages: Charming and cosy retreats perfect for those seeking a quaint experience in the countryside.
  • Apartments: Conveniently located for urban explorers, providing a comfortable home base during your stay.
  • Cabins: Rustic escapes nestled in nature, ideal for a tranquil getaway.
  • Chalets: Stylish and inviting lodgings, often found in picturesque settings for a unique holiday experience.**

Top attractions near Oakdale

Oakdale in Hudson, Columbia County, New York offers a charming mix of historic sites, picturesque lakes, and arts centres, perfect for outdoor, family and romantic getaways. The area provides a rich cultural experience, inviting visitors to explore its heritage and scenic beauty on a memorable escape. Ideal for those seeking a blend of nature and history, Oakdale promises a delightful retreat with plenty of engaging attractions to discover.

  • HITS-on-the-Hudson: Experience equestrian thrills at this nearby centre, where horseback riding amidst scenic landscapes offers a true rural charm.
  • Hudson Opera House: Enjoy a cultural treat at this arts centre, a half-mile away, where live performances and local arts enliven the community spirit.
  • Sleepy Hollow Lake: Revel in outdoor romance at this lake, boasting a beach, captivating scenery, and ideal settings for leisurely strolls.

Things to do recommended for couples

Discover romance in Oakdale, Hudson, where you can enjoy intimate walks amid picturesque landscapes and cosy dining experiences perfect for couples seeking a charming local escape.

Things to do recommended for families

Families visiting Oakdale can enjoy a day at the local park and explore interactive exhibitions at the community centre, offering educational fun for children.

Things to do recommended for groups

Groups visiting Oakdale can experience the thrill of Catamount Aerial Adventure Park, a zipline and ropes course located 26km away. This outdoor attraction offers an exhilarating adventure, perfect for bonding with friends and enjoying the beautiful natural surroundings.

*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

If you are travelling with a group, family, pets, or seeking extended stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful booking tips for using Stayz.

  • Traveling to Oakdale with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, on Stayz, you can easily filter for these options and much more.
  • Traveling to Oakdale with young kids: Traveling with young children can pose its challenges. It is essential to prioritise their comfort and safety, ensuring access to age-appropriate facilities, like a private swimming pool. Additionally, it is wise to consider accommodation that is conveniently located near family-friendly attractions.
  • Taking your pets with you to Oakdale: For many, a family holiday wouldn’t feel complete without their furry companion. If that resonates with you, we invite you to explore Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Oakdale: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in Oakdale

Oakdale offers a delightful blend of outdoor and family-friendly attractions. Visitors can enjoy the local beach and scenic lake, perfect for a romantic or adventurous escape. The area provides opportunities for a refreshing bath in Hudson and experiences in the historic Hudon area, as well as the charming Stoddard Corner neighbourhood. Its friendly atmosphere and secluded yet trendy vibe make Oakdale an ideal destination for a memorable holiday.

  • Hudson: Nestled within the vibrant region of Oakdale, Hudson boasts a seamless blend of outdoor adventure and urban delights. This city captivates travellers with its opportunities for skiing and exhilarating escapades on nearby ski fields and resorts. Iconic natural attractions, including a serene lake, majestic mountain, and inviting beach, offer a scenic backdrop for both leisurely strolls and more adventurous pursuits, ensuring a memorable exploration of nature and culture.
  • Catskill: A short 8km journey from Oakdale, Catskill presents an enticing destination for adventurers and nature lovers alike. This city invites visitors to immerse themselves in outdoor pursuits, with access to ski fields and resorts that promise a thrilling winter experience. The surrounding landscape is enriched by the presence of a towering mountain, a tranquil lake, and a captivating waterfall, offering a picturesque setting that is perfect for both active endeavours and scenic relaxation.
  • Athens: Merely 3km away from Oakdale, Athens is a charming city that exudes a blend of romance and natural splendour. Known for its outdoor and scenic appeal, the area invites travellers to partake in skiing adventures on nearby ski fields and resorts. In addition, the proximity of a serene lake, a stately mountain, and a national state park creates an idyllic environment, making Athens a delightful getaway for those seeking both tranquillity and invigorating experiences.

Booking with Stayz is a breeze

Are you keen to save on your next journey? It’s worth being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to considerable savings. To discover the perfect Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers a handy platform for you to plan new journeys, resume your previous activities, or review and arrange your travel plans. You can easily find the properties you’ve saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Thunderhart Golf Course (13.5 mi / 21.8 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)
  • 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)
  • 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.
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.
Are all fees included in the Oakdale 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 Oakdale holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Oakdale holiday homes?
You can find great discounts on holiday homes in Oakdale 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 Oakdale holiday home booking on Stayz?
To find Oakdale 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 Oakdale?
A long-stay holiday home 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 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 Oakdale holiday home?
Book your Oakdale 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 Oakdale?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakdale 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.

More holiday ideas