Sugar Loaf Holiday Rentals

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Our top choices for Sugar Loaf holiday rentals

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.
The price is NZ$325
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!
2.0 star property
The price is NZ$618
includes taxes & fees
28 Dec - 29 Dec
Cozy Modern Stay - Walk to West Point & Main St!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is NZ$456
includes taxes & fees
19 Jan - 20 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is NZ$624
includes taxes & fees
20 Jan - 21 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
The price is NZ$403
includes taxes & fees
7 Jan - 8 Jan 2026
Forava Cabins - Tiny Cabin in the Woods
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$264
includes taxes & fees
6 Jan - 7 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
3.0 star property
The price is NZ$527
includes taxes & fees
30 Dec - 31 Dec
Hike & Fish: Outdoor Retreat Near Trails
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is NZ$776
includes taxes & fees
14 Jan - 15 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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.
The price is NZ$687
includes taxes & fees
12 Jan - 13 Jan 2026
Local Artist Inspired | Walk to WestPoint + King Bed

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is NZ$496
includes taxes & fees
1 Jan - 2 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is NZ$501
includes taxes & fees
29 Dec - 30 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cottage in Middletown

Hello Small Stone
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.
The price is NZ$712
includes taxes & fees
28 Dec - 29 Dec
Hello Small Stone
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.
The price is NZ$427
includes taxes & fees
20 Jan - 21 Jan 2026
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is NZ$446
includes taxes & fees
11 Jan - 12 Jan 2026
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
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.
The price is NZ$503
includes taxes & fees
27 Jan - 28 Jan 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (5)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
The price is NZ$759
includes taxes & fees
3 Jan - 4 Jan 2026
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
10.0 out of 10, Exceptional, (33)
"The place was beautiful. Would highly recommended staying here. "
United States
Ranada
The price is NZ$505
includes taxes & fees
5 Jan - 6 Jan 2026
2 bedroom cozy condo with parking on premises

Holiday Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is NZ$644
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely 3BR Home with parking-Walk to WP Gate!

Holiday Home in Highland Falls

Fabulous 3bdrm Home w/parking!
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is NZ$591
includes taxes & fees
7 Jan - 8 Jan 2026
Fabulous 3bdrm Home w/parking!
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is NZ$521
includes taxes & fees
30 Dec - 31 Dec
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

Find out more about Sugar Loaf

Everything you need to know about Sugar Loaf holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sugar Loaf holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sugar Loaf holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sugar Loaf holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sugar Loaf holiday rentals we have selected for you start as low as NZ$264 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sugar Loaf rentals

At Expedia, we put the best Sugar Loaf holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Sugar Loaf?

Yes, there are holiday rentals close to the most popular sights in Sugar Loaf, or you can select a more 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 holiday rentals that Sugar Loaf has to offer?

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This holiday home rental outside of Sugar Loaf offers a fireplace, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area.

What are holiday rentals like in Sugar Loaf?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sugar Loaf. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.