Sugar Loaf Vacation Rentals

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Sugar Loaf vacation rentals

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!

Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$153 nightly
The price is $165
Dec 10 - Dec 11
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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

Highland Falls
10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
$271 nightly
The price is $275
Dec 10 - Dec 11
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$389 nightly
The price is $395
Dec 10 - Dec 11
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior
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
9.2 out of 10, Wonderful, (7)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
$131 nightly
The price is $148
Dec 10 - Dec 11
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed

Highland Falls
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
$406 nightly
The price is $412
Dec 10 - Dec 11
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

2.5 star property
Vernon Township
9.4 out of 10, Exceptional, (6)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
$220 nightly
The price is $249
Dec 15 - Dec 16
Total with taxes and fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen
9.8 out of 10, Exceptional, (11)
"Overall Great"
United States
Nick H.
$281 nightly
The price is $293
Dec 10 - Dec 11
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
$222 nightly
The price is $244
Dec 10 - Dec 11
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY

Greenwood Lake
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
$249 nightly
The price is $282
Jan 1 - Jan 2, 2026
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
Exterior
Forava Cabins - Tiny Cabin in the Woods

Forava Cabins - Tiny Cabin in the Woods

3.0 star property
Ringwood
$260 nightly
The price is $290
Dec 14 - Dec 15
Total with taxes and fees
Forava Cabins - Tiny Cabin in the Woods
Fridge, microwave, oven, stovetop
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Warwick
10.0 out of 10, Exceptional, (40)
"This was the best place to stay. Host was so nice to us. If we are in the area again we would definitely stay here again. "
United States
Eileen H.
$213 nightly
The price is $241
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Apartment (1 Bedroom) | Interior
Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex

3.0 star property
Newburgh
$285 nightly
The price is $322
Dec 10 - Dec 11
Total with taxes and fees
Explore & Work! Stylish Washington Heights Duplex
Dining tables
Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views

Vernon Township
9.6 out of 10, Exceptional, (18)
"It was a wonderful stay. "
United States
Veena
$223 nightly
The price is $252
Dec 10 - Dec 11
Total with taxes and fees
Cozy 2BR condo w/ valley views
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

2.0 star property
Warwick
10.0 out of 10, Exceptional, (5)
$328 nightly
The price is $371
Dec 17 - Dec 18
Total with taxes and fees
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Exterior
Hello Small Stone

Hello Small Stone

Middletown
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$369 nightly
The price is $417
Dec 10 - Dec 11
Total with taxes and fees
Hello Small Stone
Outdoor dining
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
Vernon Township
8.8 out of 10, Excellent, (3)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Dec 10 - Dec 11
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Property grounds
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

Vernon Township
10.0 out of 10, Exceptional, (3)
"We had a wonderful stay at the Appalachian Resort hosted by Milagros & Sergio. They were incredibly friendly and gave us clear and helpful explanations from the start. The room was very clean, and it was great having the water park within walking distance. They also offered flexible early check-in depending on the situation, which we really appreciated. Whenever we had questions, they responded very quickly, so we felt completely comfortable during our stay. We would love to come back again!"
United States
Young
$230 nightly
The price is $260
Dec 10 - Dec 11
Total with taxes and fees
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308
Property grounds
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, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
$272 nightly
The price is $308
Dec 10 - Dec 11
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Goshen
10.0 out of 10, Exceptional, (58)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
$473 nightly
The price is $494
Jan 4 - Jan 5, 2026
Total with taxes and fees
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
1 bedroom, desk, iron/ironing board, free WiFi
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Montgomery
10.0 out of 10, Exceptional, (2)
"Spacey, clean, best location"
United States
Assaf B.
$235 nightly
The price is $268
Dec 10 - Dec 11
Total with taxes and fees
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
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 & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"Clean room, helpful staff, great breakfast. Will stay with Hampton Inn and Suites again."
Lisa 1-night trip
Posted 1 day ago
Hampton Inn & Suites Mahwah

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 $249 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?

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This vacation home rental outside of Sugar Loaf offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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. LEGOLAND® New York and Mount Peter Ski Area 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.