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Sugar Loaf Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Sugar Loaf holiday rentals

Interior

1. 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, (3 reviews)
"fantastic accommodations"
United States
David
The price is HK$1,664
HK$4,054 total
includes taxes & fees
30 Aug - 31 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Coffee/tea maker, fridge, microwave, oven

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

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
10.0 out of 10, Exceptional, (16 reviews)
"The host was welcoming and easy to reach. It’s a lovely, fully stocked house that had everything we needed. Check-in and check-out were a breeze. Nice, quiet location."
United States
Michael M.
The price is HK$2,746
HK$5,653 total
includes taxes & fees
2 Sept - 3 Sept
Amazing Home Near West Point, Shopping, Skiing and Legoland
Living area

3. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is HK$3,452
HK$4,250 total
includes taxes & fees
17 Aug - 18 Aug
Hay Loft Apartment in Barn - Goshen
Private kitchen

4. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is HK$3,616
HK$4,452 total
includes taxes & fees
16 Aug - 17 Aug
Carriage House Apartment Goshen NY
View from room

5. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is HK$2,436
HK$3,000 total
includes taxes & fees
19 Aug - 20 Aug
Historic Horse Barn Apartment in Goshen
Interior

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
9.0 out of 10, Wonderful, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is HK$734
HK$1,257 total
includes taxes & fees
17 Aug - 18 Aug
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Smart TV

7. 6BR w/ Heated Pool, Fire Pit & Gazebo | Sleeps 22

6BR w/ Heated Pool, Fire Pit & Gazebo | Sleeps 22
Monroe
The price is HK$12,710
HK$16,011 total
includes taxes & fees
27 Aug - 28 Aug
6BR w/ Heated Pool, Fire Pit & Gazebo | Sleeps 22
Interior

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

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (13 reviews)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,961
HK$2,529 total
includes taxes & fees
25 Aug - 26 Aug
Villa Verde B&B, bsm, Greenwood Lake NY
4 bedrooms, desk, iron/ironing board, WiFi

9. Lakefront Paradise Pool + Paddle Boats Sleeps 12

Lakefront Paradise Pool + Paddle Boats Sleeps 12
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...
United States
Courtney D.
The price is HK$7,847
HK$16,280 total
includes taxes & fees
30 Aug - 31 Aug
Lakefront Paradise Pool + Paddle Boats Sleeps 12
TV, fireplace, DVD player

10. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (8 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
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Coffee/tea maker, fridge, microwave, oven

11. The Wine House, Sitting atop of Warwick's brand new Wine Bar

The Wine House, Sitting atop of Warwick's brand new Wine Bar
Warwick
10.0 out of 10, Exceptional, (36 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is HK$1,377
HK$2,294 total
includes taxes & fees
25 Aug - 26 Aug
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Exterior

12. Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is HK$2,648
HK$4,238 total
includes taxes & fees
25 Aug - 26 Aug
Modern penthouse suite in a restored grain tower with private roof deck.
Interior

13. Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks
Greenwood Lake
10.0 out of 10, Exceptional, (10 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is HK$5,254
HK$9,112 total
includes taxes & fees
13 Aug - 14 Aug
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks
Outdoor spa tub

14. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (41 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 HK$1,961
HK$4,553 total
includes taxes & fees
8 Sept - 9 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Property grounds

15. 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 HK$1,804
HK$2,840 total
includes taxes & fees
1 Sept - 2 Sept
Villa Verde B&B, Greenwood Lake NY, 1
1 bedroom, free WiFi, bed sheets

16. 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, (45 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
The price is HK$989
HK$2,174 total
includes taxes & fees
13 Aug - 14 Aug
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Smart TV

17. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is HK$1,165
HK$2,327 total
includes taxes & fees
14 Aug - 15 Aug
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior detail

18. Charming 2-bedroom apartment in the Village of Warwick

Charming 2-bedroom apartment in the Village of Warwick
Warwick
9.4 out of 10, Exceptional, (3 reviews)
"Clean, family friendly, close to everything."
United States
Milena P.
The price is HK$1,177
HK$2,538 total
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom apartment in the Village of Warwick
Property grounds

19. Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub

Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub
Greenwood Lake
9.8 out of 10, Exceptional, (8 reviews)
"Incredible place, scenic views, newly renovated house me and my family enjoyed it all! Besides that the host was very responsive and friendly."
United States
Valeryia R.
The price is HK$5,537
HK$9,052 total
includes taxes & fees
24 Aug - 25 Aug
Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub
Coffee/tea maker, fridge, microwave, oven

20. Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is HK$2,463
HK$4,219 total
includes taxes & fees
18 Aug - 19 Aug
Luxury 3BR with King Beds in Montgomery Village
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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Top Sugar Loaf Hotel Reviews

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

10/10 Excellent
"Beautiful room and Hotel just a little too pricey"
Yvette 1-night trip
Posted 2 days ago
LEGOLAND Hotel NEW York

Find out more about Sugar Loaf

Search for holiday rentals in Sugar Loaf on Expedia! You can easily find your home rentals, villas, holiday apartments in Sugar Loaf using one of the methods below:

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Frequently asked questions

Can I find a holiday rental in Sugar Loaf?

Yes, there are holiday rentals where you'll be only 4.2 mi (6.7 km) from LEGOLAND® New York, giving you a more remote option if you want a quiet place to 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 Cabin with Sauna & Firepit!: This holiday home rental outside of Sugar Loaf offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave.

What can I see and do in Sugar Loaf?

While exploring the area, visit family-friendly sights like LEGOLAND® New York, 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.