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Sugar Loaf Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$212 nightly
The price is $240
Nov 1 - Nov 2
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A room with a chandelier, a sofa, a table, and a cabinet.

2. 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, (24 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
$141 nightly
The price is $160
Nov 2 - Nov 3
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A spacious living room with a fireplace, a ceiling fan, and a large window.

3. 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
$457 nightly
The price is $517
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

4. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"It was a great place "
United States
Jose
$149 nightly
The price is $168
Oct 27 - Oct 28
Total with taxes and fees
Columbus Suites
A two-story house with a porch, a table, and chairs outside.

5. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
$202 nightly
The price is $248
Nov 8 - Nov 9
Total with taxes and fees
Historic Horse Barn Apartment in Goshen
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

6. 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.
$283 nightly
The price is $295
Nov 1 - Nov 2
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A hot tub in a lush garden with a stone wall and outdoor furniture.

7. 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.
$519 nightly
The price is $542
Nov 1 - Nov 2
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

8. 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, (20 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
$141 nightly
The price is $160
Nov 2 - Nov 3
Total with taxes and fees
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A spacious living room with a fireplace, a ceiling fan, and a large window.

9. 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
$461 nightly
The price is $545
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A dark blue door with a glass panel, flanked by two potted topiary trees, a welcome mat, and a wall-mounted light fixture.

10. 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.
$282 nightly
The price is $319
Nov 19 - Nov 20
Total with taxes and fees
Charming 2-bedroom apartment in the Village of Warwick
Interior

11. 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
$236 nightly
The price is $267
Nov 17 - Nov 18
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A patio with stone flooring, a grill, outdoor furniture, and a house with white siding and green trim.

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

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Chester
9.0 out of 10, Wonderful, (2 reviews)
"Host was very nice and accommodating. The house was clean and comfortable. There is a beautiful tub in the master bath but I was wishing there was a shower there. Master bed was very comfortable but also very tall for a shorter person like myself. Overall very nice."
United States
jolene j.
$670 nightly
The price is $791
Oct 27 - Oct 28
Total with taxes and fees
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
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
$248 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
A hot tub with a view of a lake and houses in the background.

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, (45 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.
$450 nightly
The price is $509
Nov 3 - Nov 4
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
A stone pathway leading to a stone wall with a potted plant.

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
$282 nightly
The price is $319
Nov 1 - Nov 2
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

16. 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
$257 nightly
The price is $290
Oct 27 - Oct 28
Total with taxes and fees
The Wine House
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.
$695 nightly
The price is $725
Nov 1 - Nov 2
Total with taxes and fees
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A hallway with a wooden door, a geometric light fixture, and a horse-themed painting on the wall.

18. 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.
$629 nightly
The price is $743
Oct 27 - Oct 28
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

19. 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.
$189 nightly
The price is $223
Nov 1 - Nov 2
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A clear blue pool surrounded by rocks and trees.

20. 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.
$2,547 nightly
The price is $2,659
Nov 1 - Nov 2
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
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

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury

8/10 Good
"Staff was great. Our tv didn't turn on, the staff fixed it, then it didn't work again, but we didn't care that much - we weren't there to watch tv."
Carle M 4-night trip
Posted 5 hours ago
Comfort Suites Central Valley - Woodbury

Find out more about Sugar Loaf

Everything you need to know about Sugar Loaf vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sugar Loaf vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sugar Loaf vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sugar Loaf in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sugar Loaf rentals

At Expedia, we put the best Sugar Loaf vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.