Oakdale holiday homes

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:25 Dec - 1 Jan

Sleepy Hollow Lake
Kitchen
Living room
Dining room
Exceptional
(5 reviews)

Spacious Lake Community House near Hudson

Coxsackie

9% off
NZ$8,449
for 7 nights, 1 home
NZ$1,207 per night
includes taxes & fees
Spacious Lake Community House near Hudson
Kitchen
Exterior detail
Interior
Interior
Exceptional
(71 reviews)

Beautiful Modern Swiss Cottage in Athens, NY

Athens

12% off
NZ$5,004
for 7 nights, 1 home
NZ$715 per night
includes taxes & fees
Beautiful Modern Swiss Cottage in Athens, NY
Front Door entrance
Patio accessible from dining/kitchen
Pool
Walnut dining table seats ten
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

6% off
NZ$8,875
for 7 nights, 1 home
NZ$1,268 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
NZ$1,440
for 7 nights, 1 cottage
NZ$206 per night
includes taxes & fees
1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails
Smart TV, electric fireplace, games. (Guests use their own streaming services)
Living Room
Eat-In Kitchen with seating for 4
front view from front porch
Exceptional
(15 reviews)

Cozy Quiet 3BR Fox Cottage 10 min from downtown Hudson

Hudson

23% off
NZ$1,619
for 7 nights, 1 home
NZ$231 per night
includes taxes & fees
Cozy Quiet 3BR Fox Cottage 10 min from downtown Hudson
Backyard firepit
Front door of the guest suite
Private access to the backyard, firepit, pool, BBQ and hamock.
Pool is open June-Sept.
Exceptional
(17 reviews)

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

Hudson

8% off
NZ$3,655
for 7 nights, 1 home
NZ$522 per night
includes taxes & fees
Le Soleil Suite - Pool, Mtn Views 10 Min To Hudson
Private kitchen
Exterior
Exterior
Dining
Wonderful
(7 reviews)

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

Leeds

8% off
NZ$3,008
for 7 nights, 1 apartment
NZ$430 per night
includes taxes & fees
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.
A clean, simple hallway that leads to the downstairs bedroom and bathroom.
Entertainment meets comfort here. Enjoy a movie night on the big screen.
Exceptional
(41 reviews)

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

Catskill

8% off
NZ$4,846
for 7 nights, 1 cabin
NZ$692 per night
includes taxes & fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Interior
Property grounds
Living area
Interior
Exceptional
(16 reviews)

BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN

Hudson

8% off
NZ$6,436
for 7 nights, 1 apartment
NZ$919 per night
includes taxes & fees
BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN
Interior
Pool
Living area
Exterior
Wonderful
(5 reviews)

Hudson NY’S Country Serenity Guest Suite.

Hudson

8% off
NZ$3,386
for 7 nights, 1 apartment
NZ$484 per night
includes taxes & fees
Hudson NY’S Country Serenity Guest Suite.

  • 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

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)
  • 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 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)
  • Clermont State Historic Site (14.2 mi / 22.8 km)
  • Kaaterskill Falls (15 mi / 24.1 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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Oakdale holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Oakdale to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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