Sugar Loaf Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sugar Loaf vacation rentals

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.
$189 nightly
The price is $214
May 3 - May 4
Total with taxes and fees
Historic Cabin with Pool & Fire Pit

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 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$165 nightly
The price is $179
May 6 - May 7
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!

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.
$281 nightly
The price is $293
May 2 - May 3
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

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.
$299 nightly
The price is $307
May 5 - May 6
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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, (135 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$268 nightly
The price is $268
May 3 - May 4
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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.
$381 nightly
The price is $405
May 4 - May 5
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

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
$469 nightly
The price is $490
May 3 - May 4
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit

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.
$458 nightly
The price is $465
May 4 - May 5
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
$310 nightly
The price is $325
May 7 - May 8
Total with taxes and fees
Luxury House Near West Point

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
$223 nightly
The price is $236
May 3 - May 4
Total with taxes and fees
Luxury home near West Point

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.
$313 nightly
The price is $354
May 3 - May 4
Total with taxes and fees
Hello Small Stone

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.
$131 nightly
The price is $148
May 4 - May 5
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

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 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$243 nightly
The price is $268
May 6 - May 7
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Heated Pool Hot Tubs Sauna Gym Mtn Front Appalachian @ Mtn Creek #428

Heated Pool Hot Tubs Sauna Gym Mtn Front Appalachian @ Mtn Creek #428
Vernon
$261 nightly
The price is $293
May 2 - May 3
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Mtn Front Appalachian @ Mtn Creek #428

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
$432 nightly
The price is $489
May 5 - May 6
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (54 reviews)
"Great location. Easy access in and out."
United States
Katelyn B.
$269 nightly
The price is $304
May 2 - May 3
Total with taxes and fees
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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.
$261 nightly
The price is $293
May 2 - May 3
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Deck Mtn Views Appalachian @ Mtn Creek #419

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.
$293 nightly
The price is $322
May 6 - May 7
Total with taxes and fees
Fabulous 3bdrm Home w/parking!

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
$228 nightly
The price is $257
May 4 - May 5
Total with taxes and fees
Cozy 2BR condo w/ valley views

Private Mountain Creek Getaway!

Private Mountain Creek Getaway!
Vernon Township
9.0 out of 10, Wonderful, (7 reviews)
"This place is fantastic, Charlie was extremely helpful and went above and beyond to ensure our stay was satisfactory. This place includes a lot in your stay such as towels soap/shampoo and even cotton swabs. This place is a great location and will 100% recommend for anyone staying in the area. We will definitely book again at this place and so should you if you want privacy and a great stay with a fantastic host. Thank You Charlie for the warm welcome."
United States
Cristian S.
$361 nightly
The price is $408
May 3 - May 4
Total with taxes and fees
Private Mountain Creek Getaway!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sugar Loaf Hotel Reviews

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 $243 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.

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?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9: This vacation home rental outside of Sugar Loaf is located on a lake and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.