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Sugar Loaf Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (47 reviews)
"In the area for my nephew’s graduation. Loved walking around Warwick and checking out shops.Beautiful accommodations. Very clean, easy check in, comfortable bed. Appreciated the options for coffee and tea. Overall, a great stay."
United States
Gwenda M.
$215 nightly
The price is $243
Oct 7 - Oct 8
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

2. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
$183 nightly
The price is $225
Oct 4 - Oct 5
Total with taxes and fees
Carriage House Apartment Goshen NY
A room with a chandelier, a sofa, a table, and a cabinet.

3. 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.
$143 nightly
The price is $161
Oct 13 - Oct 14
Total with taxes and fees
Room 1 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.

4. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.4 out of 10, (18 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
$153 nightly
The price is $173
Oct 13 - Oct 14
Total with taxes and fees
Cottage Suites
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, (52 reviews)
"One of the cleanest VRBOs I ever stayed in - it smelled so good. Very cozy and had everything we needed. The location is great!"
United States
Tara K.
$215 nightly
The price is $243
Nov 1 - Nov 2
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

6. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (38 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
$257 nightly
The price is $290
Oct 6 - Oct 7
Total with taxes and fees
The Wine House
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

7. 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
$143 nightly
The price is $161
Oct 4 - Oct 5
Total with taxes and fees
Room 2 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.

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.
$281 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
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.

9. 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.
$284 nightly
The price is $321
Oct 7 - Oct 8
Total with taxes and fees
Charming 2-bedroom apartment in the Village of Warwick
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

10. 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 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
$282 nightly
The price is $319
Nov 1 - Nov 2
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
A kitchen with a refrigerator, microwave, and dark cabinets.

12. The Columbus Hotel - The Residence Studio - 89-206

The Columbus Hotel - The Residence Studio - 89-206
Middletown
$197 nightly
The price is $223
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Residence Studio - 89-206
A hot tub in a lush garden with a stone wall and outdoor furniture.

13. 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, (67 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
$516 nightly
The price is $539
Nov 1 - Nov 2
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
A modern bedroom with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view into the adjacent dining area.

14. The Columbus Hotel - The Upper Studio - 52-402

The Columbus Hotel - The Upper Studio - 52-402
Middletown
$208 nightly
The price is $235
Oct 4 - Oct 5
Total with taxes and fees
The Columbus Hotel - The Upper Studio - 52-402
A hot tub with a view of a lake and houses in the background.

15. 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, (42 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.
$453 nightly
The price is $512
Oct 7 - Oct 8
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
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.
$629 nightly
The price is $743
Oct 7 - Oct 8
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$299 nightly
The price is $307
Oct 4 - Oct 5
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern hotel room with a large bed, a desk, a chair, a TV, and a wardrobe.

18. The Columbus Hotel - The Courtyard Suite - 89-303

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
$211 nightly
The price is $239
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Courtyard Suite - 89-303
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.
$207 nightly
The price is $245
Oct 6 - Oct 7
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A hotel with a green lawn, outdoor seating, and a pool area.

20. 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, (7 reviews)
"The owners responded promptly to all communication, and the unit had everything we needed to have a fun weekend at Mountain Creek. "
United States
Shane K.
$243 nightly
The price is $274
Oct 5 - Oct 6
Total with taxes and fees
Condo at Mtn Creek sleep 4 Mountain view 1 Bdr 1 Bath #308
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Comfortable hotel with breakfast that starts at 6:30am even on weekends."
Anna 1-night trip
Posted 5 hours ago
Crowne Plaza Suffern - Mahwah by IHG

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 $245 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.