Sugar Loaf holiday rentals

We found 174 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Sugar Loaf that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Sugar Loaf

Showing deals for:13 Nov - 20 Nov

Dining
Living area
Outdoor dining
Private kitchen
Exceptional
(16 reviews)

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

Harriman

12% off
AU$6,805
for 7 nights, 1 home
AU$972 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Property grounds
Room
Living area
Dining
Exceptional
(8 reviews)

Unique Dutch Barn in the Hudson Valley

Goshen

9% off
AU$6,066
for 7 nights, 1 home
AU$867 per night
includes taxes & fees
Unique Dutch Barn in the Hudson Valley
Room
Living area
Terrace/patio
Private kitchen
Exceptional
(13 reviews)

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

8% off
AU$1,925
for 7 nights, 1 cottage
AU$275 per night
includes taxes & fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Pool
Private kitchen
Living area
Terrace/patio
Exceptional
(5 reviews)

Saltwater Heated Pool • Perfect Escape in Warwick

Warwick

8% off
AU$7,229
for 7 nights, 1 home
AU$1,033 per night
includes taxes & fees
Saltwater Heated Pool • Perfect Escape in Warwick
Open floor plan living room and Dining Room with views of lake.
Lounge on your Private Deck.
Living area
Lake house directly on Greenwood Lake
Exceptional
(125 reviews)

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

Greenwood Lake

8% off
AU$3,329
for 7 nights, 1 home
AU$476 per night
includes taxes & fees
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental P25-0802
View from Master Suite
View from Master Suite
Living Room with Fire Place
Fully-Stocked Kitchen
Exceptional
(166 reviews)

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

Greenwood Lake

8% off
AU$4,989
for 7 nights, 1 home
AU$713 per night
includes taxes & fees
Large Lake House Property Your Family And Friends Will Love Staying At!
Dining
Outdoor spa tub
Interior
Private kitchen
Exceptional
(41 reviews)

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Greenwood Lake

8% off
AU$3,970
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
  • Peace of mind

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  • More quality time

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  • 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 Sugar Loaf

  • Scenic natural wonders: Sugar Loaf boasts a majestic mountain and a striking gorge, offering breathtaking views and ample hiking opportunities.
  • Outdoor adventures: Enjoy a local bike park, lakeside vistas, and family-friendly excursions in urban parks.
  • Cultural charm: The village exudes a welcoming atmosphere with artisan shops, local galleries, and seasonal festivals.
  • Leisure pursuits: A scenic golf club and national state park provide a blend of relaxation and outdoor fun.
  • Inviting local experience: The friendly locals and cosy holiday stays make Sugar Loaf a perfect retreat for both adventure and tranquillity.

Popular types of accommodation in Sugar Loaf

Welcome to Sugar Loaf, New York, a charming village that beckons with its quaint atmosphere and vibrant local culture. Nestled in the scenic Hudson Valley, Sugar Loaf offers a delightful array of attractions, including unique artisan shops, local galleries, and seasonal festivals. For your stay, explore a variety of comfortable holiday rentals, from private holiday homes to cosy apartments, perfect for enjoying all the experiences this enchanting destination has to offer.

  • Private Holiday Homes: The most sought-after accommodation choice in Sugar Loaf, offering a home-like atmosphere for families or groups.
  • Condos: A popular option, providing modern amenities and a communal living experience.
  • Apartments: Ideal for couples or solo travellers, offering convenience and comfort in a compact space.
  • Cottages: Charming and quaint, these provide a rustic escape in the heart of nature.
  • Cabins: Perfect for those seeking a secluded retreat, nestled in the woods.**

Top attractions near Sugar Loaf

Sugar Loaf offers a delightful mix of outdoor and family-friendly pursuits, with attractions such as a local bike park, a striking gorge, a scenic golf club, and a majestic mountain. Visitors can enjoy lakeside views, urban parks, and a national state park, ensuring a rich cultural and natural experience in this charming city.

  • Bear Mountain State Park: A stunning national park known for its breathtaking scenery and outdoor adventures, offering hiking trails, picnic areas, and beautiful views of the Hudson River.
  • Harriman State Park: This expansive state park is rich in history, featuring numerous hiking trails and serene lakes, perfect for exploring the natural beauty and heritage of the region.
  • Upper Greenwood Lake: A picturesque lake ideal for romantic outings, featuring scenic views and opportunities for outdoor activities such as swimming and kayaking.

Things to do recommended for couples

For a romantic getaway in Sugar Loaf, explore the quaint shops and art galleries, then enjoy a candlelit dinner at a charming local bistro. Don't miss a leisurely stroll through the scenic countryside, perfect for hand-in-hand walks, creating unforgettable memories together.

Things to do recommended for families

Families will delight in exploring the charming Sugar Loaf Village, where they can visit local artisan shops, enjoy scenic nature trails, and partake in seasonal festivals. The nearby Hudson Valley offers stunning views and family-friendly hiking trails, perfect for creating lasting memories together.

Things to do recommended for groups

Experience the thrill of motor racing at Orange County Fair Speedway, located 18km from Sugar Loaf, or embark on an adventurous day at Zoom Ziplines, 23km away, where you can soar through the trees and enjoy the great outdoors with 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 Sugar Loaf

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

  • Traveling to Sugar Loaf with a group: Think about how many bedrooms you'll require, as well as additional features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all these options and more on Stayz.
  • Traveling to Sugar Loaf with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with ensuring access to age-appropriate facilities, like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Sugar Loaf: For many, a family holiday isn’t complete without their four-legged companion. If this resonates with you, then explore Stayz properties that welcome pets. Most pet-friendly accommodations include feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Sugar Loaf: If you're after holiday lets offering deals for stays of a month or more, you've come to the right place. With the appropriate filter, you can easily locate and save on monthly rentals. You might also consider including a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Sugar Loaf

Sugar Loaf offers a delightful blend of outdoor and cultural experiences. Visitors can explore picturesque landscapes at Sugar Loaf Mountain, enjoy family-friendly excursions, and immerse themselves in the local charm of the village. With its inviting atmosphere and friendly locals, the area provides a welcoming escape for those seeking both adventure and tranquillity.

  • Middletown: Nestled 18km from Sugar Loaf, Middletown offers a vibrant city-themed experience perfect for family outings and entertainment. This bustling locale is known for its assortment of shopping centres and a large, modern shopping mall centre where visitors can explore a variety of boutique stores and eateries. The city’s attractions include an exciting theme park, a dedicated tourist precinct, and a town square, providing a blend of cultural and recreational activities ideal for a leisurely day out.
  • Goshen: Situated 10km from Sugar Loaf, Goshen is a charming city that caters to families and those seeking an entertaining urban experience. With an emphasis on city-themed attractions, visitors can enjoy a range of shopping centres and a shopping mall centre, making it a perfect destination for leisurely strolls and retail adventures. The local highlights include a captivating theme park, a bustling tourist precinct, and a picturesque square, promising a delightful blend of fun and cultural experiences.
  • Warwick: Located 10km from Sugar Loaf, Warwick is an idyllic destination for outdoor enthusiasts and adventure seekers. Renowned for its ski fields and recreational areas, this city offers a unique blend of snowy adventures and natural beauty. The landscape is enriched by scenic mountains and a tranquil lake, while a nearby theme park adds a dash of excitement to the outdoor experience, making Warwick a well-rounded destination for both thrill-seekers and nature lovers.

Best time to go to Sugar Loaf

If you're planning a trip to Sugar Loaf, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July and September to October, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.0°F (-2.2°C)Light RainMostly SunnyModerately LowAverage
February29.8°F (-1.2°C)Light RainMostly SunnyModerately LowSlightly Low
March37.4°F (3.0°C)Light RainMostly SunnyModerately LowSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageSlightly Low
May59.4°F (15.2°C)Light RainMostly SunnyAverageSlightly High
June67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
July73.9°F (23.3°C)Light RainMostly SunnyModerately HighSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnyModerately HighAverage
October54.0°F (12.2°C)Light RainMostly SunnyModerately HighAverage
November42.1°F (5.6°C)Light RainMostly SunnyAverageAverage
December34.2°F (1.2°C)Light RainMostly SunnyAverageAverage

Booking with Stayz is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a dedicated space for you to plan new journeys, refine your arrangements, or review and organise your bookings. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Sugar Loaf getaway

Learn about the unique charm of Sugar Loaf with a stay in a holiday home rental. This city is well-known for its shopping and restaurants. LEGOLAND® New York and Woodbury Common Premium Outlets are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Sugar Loaf

Do you want to find top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Sugar Loaf a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® New York (4.2 mi / 6.7 km)
  • Mount Peter Ski Area (5 mi / 8.1 km)
  • Goshen Historic Track (6 mi / 9.7 km)
  • Warwick Valley Winery and Distillery (8.3 mi / 13.3 km)
  • Brotherhood Winery (10.1 mi / 16.2 km)
  • Mountain Creek Waterpark (14.6 mi / 23.5 km)

Exploring the natural features in Sugar Loaf

Whether you're looking for adventure or just want to appreciate the scenery, Sugar Loaf is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • The Rock Sports Complex (1.8 mi / 3 km)
  • Arrow Park Lake and Lodge (6.1 mi / 9.8 km)
  • Sterling Forest State Park (8.5 mi / 13.7 km)
  • Greenwood Lake (9.4 mi / 15.1 km)
  • Lake Tiorati Beach (10.7 mi / 17.3 km)
  • Orange County Arboretum (11 mi / 17.8 km)

Transport options to and around Sugar Loaf

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Caldwell, NJ (CDW-Essex County), which is 30.7 mi (49.3 km) away.

Frequently asked questions

When is the best time to visit Sugar Loaf for a holiday rental?
September is the best time to visit Sugar Loaf for a holiday rental, as it falls within the peak season running from August to October. During this month, the weather is pleasantly warm, with temperatures generally ranging from the low teens to mid-20s Celsius, making it ideal for outdoor activities and leisurely strolls through the charming village.As autumn approaches, visitors can enjoy the stunning fall foliage that transforms the landscape into a vibrant tapestry of colours. This is particularly appealing for those looking to hike the nearby trails or explore the local art scene, with galleries and craft shops showcasing the work of talented local artisans. The picturesque setting of Sugar Loaf is great for both relaxation and adventure.For those seeking a more budget-friendly option, consider visiting in January. While this is typically the low season, it offers a unique winter experience, with opportunities for cosy indoor activities and exploring the area's winter charm at a more leisurely pace.
What are the top attractions in Sugar Loaf?
In Sugar Loaf, New York, visitors can enjoy a quaint and charming atmosphere with a range of attractions. The village is known for its vibrant arts scene, particularly at the Sugar Loaf Performing Arts Company, which hosts various performances and events throughout the year. Strolling through the village, guests can explore numerous artisan shops and galleries showcasing local crafts and artwork.The nearby Sugar Loaf Arts and Crafts Festival is a highlight, featuring local artisans and handmade goods, making it a great destination for those looking to experience the local culture. For outdoor enthusiasts, the area offers scenic hiking trails and beautiful natural landscapes, including the nearby Harriman State Park, which provides opportunities for hiking, biking, and enjoying the outdoors.Additionally, the village is close to wineries and farms, offering tastings and tours that showcase the region's agricultural products.
Are all fees included in the Sugar Loaf 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 Sugar Loaf holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sugar Loaf 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 Sugar Loaf holiday homes?
You can find great discounts on holiday homes in Sugar Loaf 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 Sugar Loaf holiday home booking on Stayz?
To find Sugar Loaf 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 Sugar Loaf?
A long-stay holiday home in Sugar Loaf 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 Sugar Loaf holiday home?
Book your Sugar Loaf 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 Sugar Loaf?
Prices for holiday homes in Sugar Loaf 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 Sugar Loaf 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.

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