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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 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)
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, (3 reviews)
"This location was perfect for our yearly fall gathering. It is 15 minutes from Pure Terror Scream Park and nestled in a historic town. The unit was clean, spacious, and perfect for a group of 7-8 people. The hosts were very helpful and prompt with instructions. I would recommend this stay if you are looking to stay in Goshen, NY."
United States
Tammy
Hay Loft Apartment in Barn - Goshen
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

3. 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 hot tub in a lush garden with a stone wall and outdoor furniture.

4. 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.
$506 nightly
The price is $529
Nov 1 - Nov 2
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

5. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"It was a great place "
United States
Jose
$143 nightly
The price is $162
Oct 20 - Oct 21
Total with taxes and fees
Columbus Suites
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.
$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 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, (47 reviews)
"Always a pleasure staying here."
United States
Natalie M.
$210 nightly
The price is $238
Nov 1 - Nov 2
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A clear blue pool surrounded by rocks and trees.

8. 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.
$2,528 nightly
The price is $2,640
Nov 1 - Nov 2
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
A two-story house with a porch, a table, and chairs outside.

9. 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 circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

10. 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.
$683 nightly
The price is $713
Nov 1 - Nov 2
Total with taxes and fees
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A dark blue door with a glass panel, flanked by two potted topiary trees, a welcome mat, and a wall-mounted light fixture.

11. 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 25 - Oct 26
Total with taxes and fees
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.

12. 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 26 - Oct 27
Total with taxes and fees
The Wine House
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
$282 nightly
The price is $319
Nov 1 - Nov 2
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
A two-story building with a porch, surrounded by greenery and a visible rainbow in the sky.

14. Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay!"
United States
Lisi M.
$472 nightly
The price is $533
Oct 25 - Oct 26
Total with taxes and fees
Modern penthouse suite in a restored grain tower with private roof deck.
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, (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.

16. 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.
$478 nightly
The price is $541
Nov 16 - Nov 17
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
A rustic cabin with a large deck and multiple windows, surrounded by dense forest.

17. Mountain View Retreat w/ Hot Tub, Theater, and Gym

Mountain View Retreat w/ Hot Tub, Theater, and Gym
Warwick
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay on a beautiful place!"
United States
Dorian G.
$1,230 nightly
The price is $1,392
Oct 21 - Oct 22
Total with taxes and fees
Mountain View Retreat w/ Hot Tub, Theater, and Gym
A modern living room with a stone fireplace, large windows, and a cozy seating area.

18. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"Great house for a big group! We were in town for a wedding and had plenty of space for 10 adults. Everything clean and a nice view from the deck. Kitchen stocked with keurig pods which was very appreciated. Big driveway which was nice.Only thing to note is there’s no communal bathrooms upstairs, 3 of the rooms have en suite bath but the 4th room needs to walk downstairs. Only relevant if you are filling all 6 king/queen rooms."
United States
Daniel S.
$1,033 nightly
The price is $1,169
Nov 1 - Nov 2
Total with taxes and fees
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

19. 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
Nov 1 - Nov 2
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A house with a view of a bridge and mountains.

20. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (148 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Oct 21 - Oct 22
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"."
Heidy 1-night trip
Posted 4 hours ago
Hampton Inn Harriman 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.