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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 room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

1. 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
Oct 4 - Oct 5
Total with taxes and fees
Room 2 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.

2. 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
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 wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

3. 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
Oct 1 - Oct 2
Total with taxes and fees
The Wine House
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

4. 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
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.
$214 nightly
The price is $242
Oct 13 - Oct 14
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

6. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
$264 nightly
The price is $325
Oct 4 - Oct 5
Total with taxes and fees
Carriage House Apartment Goshen NY
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

7. 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.
$269 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A room with a chandelier, a sofa, a table, and a cabinet.

8. 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.
$142 nightly
The price is $160
Oct 7 - Oct 8
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A modern kitchen with a central island, bar stools, a round table, and a window with a view.

9. 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.
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

10. 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
$162 nightly
The price is $183
Sep 30 - Oct 1
Total with taxes and fees
Cottage Suites
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.
$270 nightly
The price is $305
Oct 5 - Oct 6
Total with taxes and fees
Charming 2-bedroom apartment in the Village of Warwick
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, (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
Oct 7 - Oct 8
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
A hot tub with a view of a lake and houses in the background.

13. 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.
$421 nightly
The price is $476
Sep 30 - Oct 1
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
A living room with a fireplace, a sofa set, a coffee table, and a large TV mounted above the fireplace.

14. 4BD Ultimate Country Retreat w Pool in Warwick

4BD Ultimate Country Retreat w Pool in Warwick
Warwick
9.0 out of 10, Wonderful, (2 reviews)
"Me and my family decided to book this house for my baby’s 1st birthday and the host was so sweet about it. It was such a memorable time we had there and I cry every time I think of us having to come back home. We did see bears for the first time so that was scary and amazing. The pool was so comfortable and clean. They had everything you needed and more especially when cooking or baking. They allowed me to celebrate the biggest milestone of a parent’s life and I just want to say thank you so...
United States
Angelica A.
$571 nightly
The price is $646
Sep 30 - Oct 1
Total with taxes and fees
4BD Ultimate Country Retreat w Pool in Warwick
A lakeside dock with lounge chairs and a small table, surrounded by autumn foliage and a clear sky.

15. 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.
$480 nightly
The price is $543
Sep 30 - Oct 1
Total with taxes and fees
Latitude Lake House | Lake Access • Fire Pit
A stone pathway leading to a stone wall with a potted plant.

16. 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
$300 nightly
The price is $339
Sep 30 - Oct 1
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

17. 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 30 - Oct 1
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
A serene lakeside view with a golf course, houses, and a wooden dock.

18. Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
Vernon Township
10.0 out of 10, Exceptional, (44 reviews)
"My friend and I stayed for a mini golf trip and everything worked out great!"
United States
Gnanasakaran
$285 nightly
The price is $324
Sep 30 - Oct 1
Total with taxes and fees
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

19. 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.
$824 nightly
The price is $862
Sep 30 - Oct 1
Total with taxes and fees
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

20. 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.
$203 nightly
The price is $240
Oct 6 - Oct 7
Total with taxes and fees
Historic Cabin with Pool & 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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Very peaceful"
Michael 1-night trip
Posted 6 hours ago
Overlook Lodge at Bear Mountain

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 $240 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.