Sugar Loaf Holiday Rentals

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Our top choices for Sugar Loaf holiday rentals

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"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$373
includes taxes & fees
27 May - 28 May
Cozy 1-bedroom retreat minutes from West Point!

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 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.
The price is NZ$357
includes taxes & fees
14 May - 15 May
Historic Cabin with Pool & Fire Pit

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
9.0 out of 10, Wonderful, (16 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 NZ$255
includes taxes & fees
18 May - 19 May
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is NZ$398
includes taxes & fees
14 May - 15 May
Luxury home near West Point

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is NZ$706
includes taxes & fees
27 May - 28 May
Fabulous 3bdrm Home w/parking!

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, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is NZ$527
includes taxes & fees
28 May - 29 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is NZ$544
includes taxes & fees
3 June - 4 June
Luxury House Near West Point

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$710
includes taxes & fees
18 May - 19 May
House on the Babbling Brook- Quiet 2BR + King Bed!

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is NZ$511
includes taxes & fees
27 May - 28 May
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (62 reviews)
"Very good host "
United States
Binyomin
The price is NZ$993
includes taxes & fees
27 May - 28 May
Country House w/Hot Tub, Deck, Grill & Fire Pit

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is NZ$490
includes taxes & fees
14 May - 15 May
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"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$631
includes taxes & fees
14 May - 15 May
Hello Small Stone

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 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 NZ$804
includes taxes & fees
17 May - 18 May
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is NZ$375
includes taxes & fees
14 May - 15 May
Harriman Outdoor Center - Mountain Laurel Cabin

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, (5 reviews)
"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
The price is NZ$470
includes taxes & fees
14 May - 15 May
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

Heated Pool Hot Tubs Sauna Gym Deck Mtn Views Appalachian @ Mtn Creek #419

Heated Pool Hot Tubs Sauna Gym Deck Mtn Views Appalachian @ Mtn Creek #419
Vernon
9.8 out of 10, Exceptional, (10 reviews)
"The unit was very cozy, clean and well maintained, we loved the private garage and the close proximity to so many things."
United States
Matthew C.
The price is NZ$490
includes taxes & fees
14 May - 15 May
Heated Pool Hot Tubs Sauna Gym Deck Mtn Views Appalachian @ Mtn Creek #419

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (27 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
The price is NZ$429
includes taxes & fees
14 May - 15 May
Cozy 2BR condo w/ valley views

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

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Warwick
10.0 out of 10, Exceptional, (5 reviews)
"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$720
includes taxes & fees
26 May - 27 May
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Slope side cozy Studio

Slope side cozy Studio
Vernon Township
The price is NZ$369
includes taxes & fees
14 May - 15 May
Slope side cozy Studio

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, (35 reviews)
"Clean & organized, was a perfect location for our family trip."
United States
Rodney L.
The price is NZ$563
includes taxes & fees
19 May - 20 May
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
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$483 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?

Perfect and Spacious Hudson Valley Escape!: This holiday home rental outside of Sugar Loaf has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.