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Sugar Loaf Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Sugar Loaf vacation rentals

A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

1. 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, (48 reviews)
"Always a pleasure staying here."
United States
Natalie M.
The price is ￥15,107
￥37,321 total
includes taxes & fees
Nov 1 - Nov 2
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

2. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"It was a great place "
United States
Jose
The price is ￥12,499
￥25,674 total
includes taxes & fees
Oct 27 - Oct 28
Columbus Suites
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

3. 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
8.6 out of 10, Excellent, (19 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is ￥13,554
￥25,095 total
includes taxes & fees
Nov 2 - Nov 3
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
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
4.0 star property
Goshen
The price is ￥27,655
￥34,049 total
includes taxes & fees
Nov 8 - Nov 9
Historic Horse Barn Apartment in Goshen
Interior

5. 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, (53 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 ￥19,452
￥41,880 total
includes taxes & fees
Nov 17 - Nov 18
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
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, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is ￥13,695
￥24,721 total
includes taxes & fees
Nov 3 - Nov 4
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

7. 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 ￥23,295
￥45,895 total
includes taxes & fees
Nov 1 - Nov 2
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A dark blue door with a glass panel, flanked by two potted topiary trees, a welcome mat, and a wall-mounted light fixture.

8. 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 ￥23,531
￥50,577 total
includes taxes & fees
Nov 19 - Nov 20
Charming 2-bedroom apartment in the Village of Warwick
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

9. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (39 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
The price is ￥27,531
￥45,521 total
includes taxes & fees
Oct 26 - Oct 27
The Wine House
A hot tub in a lush garden with a stone wall and outdoor furniture.

10. 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 ￥44,237
￥82,960 total
includes taxes & fees
Nov 1 - Nov 2
Country House w/Hot Tub, Deck, Grill & Fire Pit
A stone pathway leading to a stone wall with a potted plant.

11. 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 ￥31,374
￥50,045 total
includes taxes & fees
Nov 1 - Nov 2
Villa Verde B&B, Greenwood Lake NY, 1
A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

12. 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 ￥64,881
￥111,892 total
includes taxes & fees
Nov 1 - Nov 2
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

13. 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 ￥34,511
￥44,011 total
includes taxes & fees
Nov 1 - Nov 2
Villa Verde B&B, bsm, Greenwood Lake NY
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 ￥18,467
￥36,640 total
includes taxes & fees
Nov 2 - Nov 3
Historic Cabin with Pool & Fire Pit
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

15. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,040
￥48,139 total
includes taxes & fees
Oct 26 - Oct 27
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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 ￥54,905
￥116,556 total
includes taxes & fees
Oct 27 - Oct 28
Amazing Home Near West Point, Shopping, Skiing and Legoland
A hotel with a green lawn, outdoor seating, and a pool area.

17. 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)
"The property was perfect for our family. It was clean and a comfortable space. The resort was very nice and had all the amenities you would want. The host was very attentive and available to answer any questions. We had a fantastic stay!"
United States
Pamela D.
The price is ￥20,393
￥43,365 total
includes taxes & fees
Oct 26 - Oct 27
Condo at Mtn Creek sleep 4 Mountain view 1 Bdr 1 Bath #308
A clear blue pool surrounded by rocks and trees.

18. Spectacular Historic Mansion w/Pool&Tennis

Spectacular Historic Mansion w/Pool&Tennis
Goshen
10.0 out of 10, Exceptional, (20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
The price is ￥250,678
￥414,199 total
includes taxes & fees
Nov 1 - Nov 2
Spectacular Historic Mansion w/Pool&Tennis
A sign for Minerals Resort & Spa with directions to parking, hotel registration, and the Elements Spa.

19. Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Vernon Township
9.8 out of 10, Exceptional, (67 reviews)
"Would definitely stay here again! It was clean and plenty of space!"
United States
Sandeep
The price is ￥17,648
￥47,883 total
includes taxes & fees
Oct 26 - Oct 27
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
A living room with a sofa, coffee table, TV, and dining area with chairs and a table.

20. Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (33 reviews)
"Great place, would come back. Great host communication."
United States
Adriana
The price is ￥16,236
￥40,985 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 2BR condo w/ valley views
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

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"Clean property but highway noise was nonstop. Not sure if there was an option to stay at the back or other side of the hotel. If so, would highly recommend it."
daphne 1-night trip
Posted 15 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG

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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Look no further and take a look at our great range of rental properties in Sugar Loaf!

Frequently asked questions

Can I find a vacation rental in Sugar Loaf?

Yes, we have vacation rentals near the most popular sights in Sugar Loaf, or you can choose a 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 vacation rentals in Sugar Loaf?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Sugar Loaf is located on a lake and has a patio, a garden, and a barbecue grill 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 larger area.

What are vacation rentals like in Sugar Loaf?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Sugar Loaf. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.