Sugar Loaf Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Sugar Loaf holiday rentals

Interior

1. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (55 reviews)
"Great location in the heart of Warwick, NY. Easy to walk around town and visit the local restaurants!"
United States
Francis
The price is NZ$424
includes taxes & fees
16 Nov - 17 Nov
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

2. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (23 reviews)
"Great place, but you can hear red everything going on outside your room with the restaurant downstairs and other people in the common area. But I’d definitely come back here"
United States
Joseph
The price is NZ$275
includes taxes & fees
16 Nov - 17 Nov
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

3. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is NZ$264
includes taxes & fees
19 Nov - 20 Nov
Columbus Suites
A two-story house with a porch, a table, and chairs outside.

4. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
3.5 star property
Goshen
Historic Horse Barn Apartment in Goshen
A spacious living room with a fireplace, a ceiling fan, and a large window.

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
The price is NZ$927
includes taxes & fees
30 Nov - 1 Dec
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A room with a chandelier, a sofa, a table, and a cabinet.

6. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (28 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is NZ$260
includes taxes & fees
17 Nov - 18 Nov
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

7. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (49 reviews)
"Always a pleasure staying here."
United States
Natalie M.
The price is NZ$426
includes taxes & fees
15 Nov - 16 Nov
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

8. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is NZ$501
includes taxes & fees
14 Nov - 15 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A patio with stone flooring, a grill, outdoor furniture, and a house with white siding and green trim.

9. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Chester
8.8 out of 10, Excellent, (3 reviews)
"Thank you for the weekend. We had a great time and Sugarloaf was a great location for us all to catch up."
United States
Jeff S.
The price is NZ$1,304
includes taxes & fees
17 Nov - 18 Nov
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

10. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (40 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
The price is NZ$485
includes taxes & fees
24 Nov - 25 Nov
The Wine House
A spacious living room with a fireplace, a ceiling fan, and a large window.

11. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is NZ$962
includes taxes & fees
30 Nov - 1 Dec
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A hot tub in a lush garden with a stone wall and outdoor furniture.

12. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (69 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is NZ$917
includes taxes & fees
18 Nov - 19 Nov
Country House w/Hot Tub, Deck, Grill & Fire Pit
A stone pathway leading to a stone wall with a potted plant.

13. Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is NZ$537
includes taxes & fees
21 Nov - 22 Nov
Villa Verde B&B, Greenwood Lake NY, 1
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

14. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is NZ$414
includes taxes & fees
16 Nov - 17 Nov
Historic Cabin with Pool & Fire Pit
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

15. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (14 reviews)
"The breakfast was lovely!"
United States
Tara
The price is NZ$472
includes taxes & fees
21 Nov - 22 Nov
Villa Verde B&B, bsm, Greenwood Lake NY
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

16. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
The price is NZ$1,231
includes taxes & fees
22 Nov - 23 Nov
Amazing Home Near West Point, Shopping, Skiing and Legoland
A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

17. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is NZ$1,189
includes taxes & fees
15 Nov - 16 Nov
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A hotel with a green lawn, outdoor seating, and a pool area.

18. Condo at Mtn Creek sleep 4 Mountain view 1 Bdr 1 Bath #308

Condo at Mtn Creek sleep 4 Mountain view 1 Bdr 1 Bath #308
Vernon Township
10.0 out of 10, Exceptional, (8 reviews)
"Very nice property and attentive hosts!"
United States
Louis S.
The price is NZ$465
includes taxes & fees
23 Nov - 24 Nov
Condo at Mtn Creek sleep 4 Mountain view 1 Bdr 1 Bath #308
A hot tub with a view of a lake and houses in the background.

19. Waterfront Home with Hot Tub, Firepit, and Kayaks

Waterfront Home with Hot Tub, Firepit, and Kayaks
Greenwood Lake
10.0 out of 10, Exceptional, (47 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is NZ$864
includes taxes & fees
1 Dec - 2 Dec
Waterfront Home with Hot Tub, Firepit, and Kayaks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Find holiday rentals that suit your style

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Top Sugar Loaf Hotel Reviews

A hotel with a modern facade, multiple floors, and a covered entrance area.
Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown

10/10 Excellent

This was just a quick 1 night stopover but the room was perfect and reception polite and welcoming. Firstly the room was clean and large enough for a family to move freely. The beds were comfortable and the room well serviced. Breakfast was your standard pancakes, sausage eggs etc but still nice.
Australia
Allison
Reviewed December 23, 2019
Holiday Inn Express & Suites Middletown - Goshen by IHG

Find out more about Sugar Loaf

Everything you need to know about Sugar Loaf holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sugar Loaf holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sugar Loaf holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sugar Loaf holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sugar Loaf. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sugar Loaf holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sugar Loaf holiday rentals we have selected for you start as low as NZ$258 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sugar Loaf rentals

At Expedia, we put the best Sugar Loaf holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sugar Loaf rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sugar Loaf holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sugar Loaf. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Sugar Loaf?

Yes, there are holiday rentals close to the most popular sights in Sugar Loaf, or you can select a more secluded option if you're looking for a relaxing stay. Sugar Loaf is known for its shopping and restaurants.

What are some of the best holiday rentals that Sugar Loaf has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Sugar Loaf is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Sugar Loaf?

While exploring the area, visit family-friendly sights like Castle Fun Center, or get outside and enjoy nature at The Rock Sports Complex. Sugar Loaf Performing Arts Center and Woodbury Common Premium Outlets are a couple of places you'll find in the wider area.

What are holiday rentals like in Sugar Loaf?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sugar Loaf. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.