Sugar Loaf Vacation Rentals

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Our top choices for Sugar Loaf vacation 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 CA $168
CA $308 total
includes taxes & fees
May 27 - May 28
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 CA $182
CA $336 total
includes taxes & fees
May 28 - May 29
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 CA $117
CA $207 total
includes taxes & fees
May 27 - May 28
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 CA $273
CA $328 total
includes taxes & fees
May 14 - May 15
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 CA $338
CA $584 total
includes taxes & fees
May 27 - May 28
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 CA $257
CA $438 total
includes taxes & fees
May 19 - May 20
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 CA $274
CA $449 total
includes taxes & fees
Jun 3 - Jun 4
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 CA $212
CA $590 total
includes taxes & fees
May 18 - May 19
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 CA $157
CA $422 total
includes taxes & fees
May 27 - May 28
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 CA $450
CA $813 total
includes taxes & fees
May 19 - May 20
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 CA $203
CA $402 total
includes taxes & fees
May 19 - May 20
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 CA $184
CA $527 total
includes taxes & fees
May 14 - May 15
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 CA $231
CA $672 total
includes taxes & fees
May 17 - May 18
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 CA $268
CA $308 total
includes taxes & fees
May 19 - May 20
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 CA $176
CA $376 total
includes taxes & fees
May 14 - May 15
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 CA $188
CA $405 total
includes taxes & fees
May 19 - May 20
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 CA $142
CA $358 total
includes taxes & fees
May 14 - May 15
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 CA $253
CA $592 total
includes taxes & fees
May 19 - May 20
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Slope side cozy Studio

Slope side cozy Studio
Vernon Township
The price is CA $124
CA $298 total
includes taxes & fees
May 14 - May 15
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 CA $239
CA $467 total
includes taxes & fees
May 19 - May 20
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sugar Loaf. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Perfect and Spacious Hudson Valley Escape!: This vacation 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 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.