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Sugar Loaf Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Sugar Loaf vacation rentals

A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

1. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
$292 nightly
The price is $360
Oct 4 - Oct 5
Total with taxes and fees
Carriage House Apartment Goshen NY
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

2. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Hay Loft Apartment in Barn - Goshen
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
$137 nightly
The price is $155
Sep 28 - Sep 29
Total with taxes and fees
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
$391 nightly
The price is $481
Oct 3 - Oct 4
Total with taxes and fees
Historic Horse Barn Apartment in Goshen
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

5. 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.
$209 nightly
The price is $236
Sep 27 - Sep 28
Total with taxes and fees
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.

6. 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
$154 nightly
The price is $174
Oct 13 - Oct 14
Total with taxes and fees
Cottage Suites
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

7. 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
$250 nightly
The price is $283
Oct 1 - Oct 2
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

8. 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
$246 nightly
The price is $278
Sep 27 - Sep 28
Total with taxes and fees
The Wine House
A room with a chandelier, a sofa, a table, and a cabinet.

9. 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.
$144 nightly
The price is $163
Oct 7 - Oct 8
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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.
$270 nightly
The price is $305
Sep 30 - Oct 1
Total with taxes and fees
Charming 2-bedroom apartment in the Village of Warwick
A hot tub with a view of a lake and houses in the background.

11. 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.
$448 nightly
The price is $507
Sep 29 - Sep 30
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

12. 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.
$212 nightly
The price is $240
Sep 28 - Sep 29
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

13. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (16 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$269 nightly
The price is $281
Sep 27 - Sep 28
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A modern kitchen with a central island, bar stools, a round table, and a window with a view.

14. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
$403 nightly
The price is $456
Sep 28 - Sep 29
Total with taxes and fees
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
A hallway with a black door labeled '207', a fire alarm, and a laundry room with two washing machines.

15. The Columbus Hotel - The Gold Suite - 89-207

The Columbus Hotel - The Gold Suite - 89-207
Middletown
$208 nightly
The price is $235
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Gold Suite - 89-207
A lakeside dock with lounge chairs and a small table, surrounded by autumn foliage and a clear sky.

16. Latitude Lake House | Lake Access • Fire Pit

Latitude Lake House | Lake Access • Fire Pit
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Great property and loved the lake access!"
United States
Dan and Kristen L.
$437 nightly
The price is $494
Sep 28 - Sep 29
Total with taxes and fees
Latitude Lake House | Lake Access • Fire Pit
A modern hotel room with a large bed, a desk, a chair, a TV, and a wardrobe.

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

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
$173 nightly
The price is $195
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Courtyard Suite - 89-303
A staircase with a fire alarm and a row of lockers.

18. The Columbus Hotel - The Market Suite - 52-202

The Columbus Hotel - The Market Suite - 52-202
Middletown
$176 nightly
The price is $199
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Market Suite - 52-202
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

19. 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.
$594 nightly
The price is $702
Sep 28 - Sep 29
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
A hot tub in a lush garden with a stone wall and outdoor furniture.

20. 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.
$544 nightly
The price is $569
Sep 27 - Sep 28
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
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
"Was definitely worth the price. Much more than I expected for this area. Friendly staff, clean rooms, convenient location and very comfortable."
ELANA 1-night trip
Posted 2 hours ago
Holiday Inn Express Hotel & Suites Chester 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 $221 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.