Default HTG hotel image

Sugar Loaf Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Sugar Loaf vacation 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 ￥17,618
￥36,990 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥14,142
￥24,438 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥9,841
￥22,804 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥26,189
￥82,682 total
includes taxes & fees
Nov 30 - Dec 1
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 ￥13,373
￥23,082 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥16,999
￥38,083 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥23,570
￥44,373 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥43,807
￥119,245 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥27,855
￥43,724 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥33,649
￥85,619 total
includes taxes & fees
Nov 30 - Dec 1
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 ￥44,759
￥81,717 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥31,744
￥46,505 total
includes taxes & fees
Nov 13 - Nov 14
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 ￥19,440
￥36,836 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥34,918
￥40,938 total
includes taxes & fees
Nov 13 - Nov 14
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 ￥55,552
￥111,931 total
includes taxes & fees
Dec 4 - Dec 5
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 ￥65,647
￥105,752 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥20,634
￥41,814 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥31,109
￥76,668 total
includes taxes & fees
Dec 1 - Dec 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugar Loaf Hotel Reviews

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Clean, friendly, great location, great restaurants"
Caroline 2-night trip
Posted 4 hours ago
The Thayer Hotel at West Point

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:

  • View our selection of featured holiday rentals in Sugar Loaf
  • Use the map to find apartments and other holiday homes in the Sugar Loaf neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sugar Loaf while they last

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.