Holiday Rentals in Sugar Loaf

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Our top choices for Sugar Loaf holiday rentals

9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
The price is €227
includes taxes & fees
26 Jan - 27 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.2 out of 10, Wonderful, (10 reviews)
"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 €330
includes taxes & fees
27 Jan - 28 Jan
Local Artist Inspired | Walk to WestPoint + King Bed
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is €284
includes taxes & fees
22 Jan - 23 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (3 reviews)
"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 €337
includes taxes & fees
21 Jan - 22 Jan
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is €166
includes taxes & fees
18 Feb - 19 Feb
Cozy 1-bedroom retreat minutes from West Point!
2.0 star property
Rustic Lakefront Studio w Deck Workspace
3.0 star property
10.0 out of 10, Exceptional, (1 review)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
The price is €224
includes taxes & fees
21 Jan - 22 Jan
Forava Cabins - Tiny Cabin in the Woods
2.0 star property
The price is €163
includes taxes & fees
21 Jan - 22 Jan
Studio Retreat | Near Woodbury Commons & Legoland
9.4 out of 10, Exceptional, (8 reviews)
"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 €137
includes taxes & fees
2 Feb - 3 Feb
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is €253
includes taxes & fees
1 Feb - 2 Feb
Villa Verde B&B, bsm, Greenwood Lake NY

Holiday Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7 reviews)
"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 €261
includes taxes & fees
21 Jan - 22 Jan
Lovely 3BR Home with parking-Walk to WP Gate!
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
The price is €230
includes taxes & fees
1 Feb - 2 Feb
Villa Verde B&B, Greenwood Lake NY, 1

Condo in Vernon Township

Cozy 2BR condo w/ valley views
9.4 out of 10, Exceptional, (22 reviews)
"The condo was perfect for our last minute trip. The condo was clean and close the ski area. My family enjoyed our stay there. Thank you."
United States
Richard
The price is €221
includes taxes & fees
21 Jan - 22 Jan
Cozy 2BR condo w/ valley views
10.0 out of 10, Exceptional, (34 reviews)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is €236
includes taxes & fees
1 Feb - 2 Feb
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our short stay at the house - it was extremely clean, the beds were comfortable, and the whole house was warm and cozy. There were thoughtful little touches all around the house - from fluffy socks for us to extra blankets, motion-sensor nightlights, and a fully equipped kitchen. Everything is newly renovated and updated. Views of the surrounding mountains are beautiful and the location is quiet and peaceful. We would visit again! "
United States
Anne R.
The price is €358
includes taxes & fees
21 Jan - 22 Jan
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
2.0 star property
The price is €249
includes taxes & fees
21 Jan - 22 Jan
Bright Studio Retreat w Deck Nature Views
9.2 out of 10, Wonderful, (7 reviews)
"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 €218
includes taxes & fees
21 Jan - 22 Jan
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
9.8 out of 10, Exceptional, (131 reviews)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is €266
includes taxes & fees
21 Jan - 22 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Holiday Home in Highland Falls

Fabulous 3bdrm Home w/parking!
9.0 out of 10, Wonderful, (4 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is €254
includes taxes & fees
21 Jan - 22 Jan
Fabulous 3bdrm Home w/parking!

Apartment in Highland Falls

Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (21 reviews)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is €219
includes taxes & fees
21 Jan - 22 Jan
Walk to WP Gate + Free 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

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, apart-hotels, 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 €221 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.