Photo by Joe Vickiana

Southfields holiday rentals

We found 181 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Southfields that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as cable TV and a washer and dryer. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Southfields

Showing deals for:18 Dec - 25 Dec

Dining
Private kitchen
Exterior
Interior
Exceptional
(17 reviews)

Amazing Home Near West Point, Shopping, Skiing and Legoland

Monroe

7% off
AU$4,338
for 7 nights, 1 home
AU$620 per night
includes taxes & fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
Living area
Private kitchen
Terrace/patio
Pool
Exceptional
(5 reviews)

Saltwater Heated Pool • Perfect Escape in Warwick

Warwick

8% off
AU$4,239
for 7 nights, 1 home
AU$606 per night
includes taxes & fees
Saltwater Heated Pool • Perfect Escape in Warwick
Dining
Living area
Outdoor dining
Pool
Exceptional
(16 reviews)

The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC

Harriman

12% off
AU$8,595
for 7 nights, 1 home
AU$1,228 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Living Room with Fire Place
View from Master Suite
Dining
View from Master Suite
Exceptional
(168 reviews)

Large Lake House Property Your Family And Friends Will Love Staying At!

Greenwood Lake

8% off
AU$5,222
for 7 nights, 1 home
AU$746 per night
includes taxes & fees
Large Lake House Property Your Family And Friends Will Love Staying At!
Open floor plan living room and Dining Room with views of lake.
Lounge on your Private Deck.
Living area
Entrance to fully fenced in yard to front door and through to the lake!
Exceptional
(125 reviews)

Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental P25-0802

Greenwood Lake

8% off
AU$3,643
for 7 nights, 1 home
AU$520 per night
includes taxes & fees
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental P25-0802
Living Room with sofa bed
Kitchen Island
Deck
2nd Floor Apt with Private Entrances, front and back.
Exceptional
(67 reviews)

Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries

Chester

7% off
AU$2,130
for 7 nights, 1 apartment
AU$304 per night
includes taxes & fees
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Exterior
Outdoor spa tub
Room
Dining
Exceptional
(15 reviews)

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

12% off
AU$4,544
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Interior
Outdoor spa tub
Living area
Dining
Exceptional
(41 reviews)

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Greenwood Lake

8% off
AU$6,036
for 7 nights, 1 home
AU$862 per night
includes taxes & fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

  • 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

Find the perfect holiday rental for your Southfields getaway

Learn about the unique charm of Southfields with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Southfields

Are you searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southfields a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mount Peter Ski Area (6.7 mi / 10.8 km)
  • LEGOLAND® New York (11.3 mi / 18.1 km)
  • Brotherhood Winery (12.1 mi / 19.5 km)
  • West Point Golf Course (12.6 mi / 20.3 km)
  • Goshen Historic Track (12.9 mi / 20.8 km)
  • Campgaw Mountain Ski Area (13.7 mi / 22.1 km)

Exploring the natural landscape of Southfields

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Southfields. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Arrow Park Lake and Lodge (2.1 mi / 3.4 km)
  • Lake Tiorati Beach (4.2 mi / 6.8 km)
  • Lake Welch Beach (5.1 mi / 8.2 km)
  • Sterling Forest State Park (6.2 mi / 10 km)
  • The Rock Sports Complex (8.4 mi / 13.6 km)
  • Greenwood Lake (9.5 mi / 15.2 km)

Transport options to and around Southfields

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 17.3 mi (27.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Caldwell, NJ (CDW-Essex County), which is 26.9 mi (43.4 km) away.

Frequently asked questions

What is the best area to stay in Southfields when booking a holiday rental?
When considering a holiday rental in Southfields, New York, the area surrounding the charming hamlet itself is quite appealing. Southfields is located near the stunning Harriman State Park, which offers an abundance of outdoor activities such as hiking, fishing, and birdwatching. The peaceful, rural atmosphere makes it an ideal spot for those looking to escape the hustle and bustle of city life.In terms of property options, Southfields features a selection of charming cottages and spacious homes, great for families or groups seeking a tranquil getaway. The nearby town of Warwick is also worth exploring, known for its picturesque Main Street filled with boutique shops, delightful eateries, and local wineries.For those keen on cultural experiences, the historic sites in the vicinity, such as the Warwick Valley Winery and Distillery, provide a taste of the local flavour.
When is the best time to visit Southfields for a holiday rental?
The peak season in Southfields runs from May to July, making it the most popular time for visitors eager to enjoy the region's beautiful landscapes and outdoor activities. During these months, you can expect vibrant greenery and pleasant weather, superb for hiking the nearby trails or exploring the charming local farms and vineyards. July stands out as a highlight, welcoming many travellers who are drawn to the area's attractions and the lively summer atmosphere.While the summer months are bustling with activity, they also offer a range of experiences for all preferences. The comfortable temperatures, typically hovering around 20 to 30 degrees Celsius, allow for enjoyable sightseeing and outdoor fun, whether you're picnicking in a park or attending local events.For those seeking a more budget-friendly option, consider planning your visit in January. This quieter month can provide a unique opportunity to enjoy Southfields' serene winter landscape and explore the area at a relaxed pace, free from the summer crowds.Ultimately, the best time to visit Southfields for a holiday rental depends on your interests.
What are the top attractions in Southfields?
In Southfields, New York, visitors can explore the scenic beauty of the region, particularly within the nearby Harriman State Park, which offers a variety of outdoor activities such as hiking, biking, and picnicking. The park features numerous trails and picturesque lakes, making it a popular spot for nature enthusiasts.Additionally, the area is close to the historic Bear Mountain State Park, where you can enjoy stunning views of the Hudson River and the surrounding mountains, as well as a zoo and a variety of recreational facilities.For those interested in local culture, the quaint village atmosphere of Southfields itself provides charming shops and eateries, ideal for a leisurely stroll.
Are all fees included in the Southfields 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 Southfields holiday homes with parking?
Stayz offers a wide selection of holiday homes in Southfields 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 Southfields holiday homes?
You can find great discounts on holiday homes in Southfields 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 Southfields holiday home booking on Stayz?
To find Southfields 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 Southfields?
A long-stay holiday home in Southfields 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 Southfields holiday home?
Book your Southfields 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 Southfields?
Prices for holiday homes in Southfields 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 Southfields 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.