Sugar Loaf Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Sugar Loaf

Fridge, oven, stovetop, cookware/dishes/utensils
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)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$726
HK$1,473 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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

Highland Falls
10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is HK$699
HK$2,138 total
includes taxes & fees
16 Nov - 17 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

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

Highland Falls
9.4 out of 10, Exceptional, (3)
"Home was very peaceful and serene, My Boys really enjoyed the relaxing and laid back vibe this stay had to offer. My kids did mention it would be a summer vacation stay, because of the creek in the back. Overall is was clean and accommodating. Host did their best for all my accommodation. I would give them a 5- Star White Glove on this. Thanks, Hope to revisit! "
United States
Akail S.
The price is HK$855
HK$3,376 total
includes taxes & fees
17 Nov - 18 Nov
3BR West Point Retreat-3min to Back Gate+ King Bed
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

2.5 star property
Vernon Township
9.4 out of 10, Exceptional, (6)
"This was my family’s first Vrbo experience and we couldn’t be more happy with the property! The owner, Henry, was very quick to respond when we needed a little guidance on to check in and also made sure to check in with me later on to see if we settled in ok. The property was super cute and quaint for our snowboarding trip. We cannot wait to come back again! "
United States
Samantha
The price is HK$699
HK$1,827 total
includes taxes & fees
19 Nov - 20 Nov
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Children’s area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen
9.8 out of 10, Exceptional, (11)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
United States
Teresa
The price is HK$1,154
HK$2,274 total
includes taxes & fees
17 Nov - 18 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Fridge, microwave, oven, stovetop
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, (4)
"The apartment was awesome. Wish we were able to stay for more than just the one night. The host was responding to questions almost before I was done typing the question:) Everything was clean and orderly, parking was close (About 8 inches from the door.) We are picking up more work in the area and hope to stay again next trip."
United States
Peter F.
The price is HK$1,216
HK$2,193 total
includes taxes & fees
19 Nov - 20 Nov
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior
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, (3)
"Good stay, awesome place"
United States
Scott G.
The price is HK$1,150
HK$3,277 total
includes taxes & fees
23 Nov - 24 Nov
House on the Babbling Brook- Quiet 2BR + King Bed!
TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!

Cozy Haven: A Romantic Retreat in our Tiny House!

Middletown
7.0 out of 10, Good, (9)
"I love the place but the cleanliness was bad, we found a condom under the bed and there was also blood on the bed sheets and a yellow stain on the bed. I’m sorry but for the price I expected something better than this."
United States
Jeferson Eleazar P.
The price is HK$855
HK$1,918 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Haven: A Romantic Retreat in our Tiny House!
Interior
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, (6)
"Although the original check-in process was fine, the host became unresponsive to our questions during the stay. We were able to figure out the answers to our questions, but it would have been nice to hear anything at all. We went so far as to text the host because we became concerned after radio silence for 3 days. Once she did respond she didn't apologize for not getting back to us and ghosting us for days. "
United States
Patty M.
The price is HK$643
HK$1,150 total
includes taxes & fees
17 Nov - 18 Nov
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Fridge, microwave, oven, stovetop
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Warwick
10.0 out of 10, Exceptional, (39)
"We absolutely loved this place! Very clean, comfortable, and the host was super communicative. We loved being able to walk to all the bars and restaurants. "
United States
Anna R.
The price is HK$831
HK$1,908 total
includes taxes & fees
17 Nov - 18 Nov
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Interior
Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex

3.0 star property
Newburgh
The price is HK$1,259
HK$2,390 total
includes taxes & fees
15 Nov - 16 Nov
Explore & Work! Stylish Washington Heights Duplex
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls
10.0 out of 10, Exceptional, (7)
"Celebrated my son’s HS graduation with my father-in-law along for the adventure, Joe’s townhouse is super convenient to Thayer Gate and eating establishments along Main St. Grill worked well and the beds made for sound slumber. For mixed company an extra half bath might be desired, but 3 guys who know each other well managed just fine. The basement washer & dryer are top of line."
United States
James W.
The price is HK$1,294
HK$2,539 total
includes taxes & fees
16 Nov - 17 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY

Greenwood Lake
10.0 out of 10, Exceptional, (12)
"Definitely going back "
United States
Vincent
The price is HK$1,453
HK$2,549 total
includes taxes & fees
16 Nov - 17 Nov
Villa Verde B&B, bsm, Greenwood Lake NY
Exterior
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Montgomery
10.0 out of 10, Exceptional, (1)
"Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!"
United States
Emma C.
The price is HK$1,430
HK$2,224 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Exterior
Hello Small Stone

Hello Small Stone

Middletown
9.6 out of 10, Exceptional, (5)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
United States
David
The price is HK$1,294
HK$3,292 total
includes taxes & fees
16 Nov - 17 Nov
Hello Small Stone
1 bedroom, desk, iron/ironing board, free WiFi
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Montgomery
10.0 out of 10, Exceptional, (2)
"Location was fantastic - short short walk (100-300’) to a handful of very good restaurants. The apartment is brand new, extraordinarily clean, well provisioned and has everything you could possibly need. It’s clear that the owners take pride in their property and take care of it accordingly. They are also super responsive and helpful. I accidentally locked myself out of the apartment one morning and "
United States
Ryan B.
The price is HK$1,049
HK$1,845 total
includes taxes & fees
10 Dec - 11 Dec
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is HK$1,010
HK$3,422 total
includes taxes & fees
17 Nov - 18 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls
8.0 out of 10, Very good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
The price is HK$1,294
HK$2,474 total
includes taxes & fees
16 Nov - 17 Nov
Fabulous 3bdrm Home w/parking!
Dining tables
Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views

Vernon Township
9.6 out of 10, Exceptional, (18)
"Great location, spacious and super cozy w comfy linens and beds. 3 mins to mountain. Provides toiletries, great communication. Great local neighbors & residents "
United States
Jennifer D.
The price is HK$769
HK$1,967 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2BR condo w/ valley views
Property grounds
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, (3)
"The space was wonderful and exactly as shown in listing. Hosts are so communicative up to day of check-out. It was fun to have some games on hand to curl up and play while enjoying the fireplace in the evening. The fridge size made it so convenient to make our meals and enjoy going out and about in the area during the day. Would definitely book the space again, best condo we've stayed at in this location to date. It was a wonderful space to incorporate in our post-engagement weekend getaway with...
United States
Dawn A.
The price is HK$971
HK$2,080 total
includes taxes & fees
17 Nov - 18 Nov
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugar Loaf Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Best hotel I’ve stayed in for a while. Very clean, friendly staff, very comfortable. Walking distance to everything. Breakfast was excellent. We stayed 5 nights and breakfast was different every day…. Fried eggs, scramble, omelet, sausage, bacon, empanadas, waffles, it was excellent!"
Michelle 5-night trip
Posted 2 days ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Sugar Loaf

Search for holiday rentals in Sugar Loaf on Expedia! You can easily find your home rentals, villas, holiday apartments in Sugar Loaf using one of the methods below:

  • View our selection of featured holiday rentals in Sugar Loaf
  • Use the map to find apartments and other holiday homes in the Sugar Loaf neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sugar Loaf while they last

Look no further and take a look at our great range of rental properties in Sugar Loaf!

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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Sugar Loaf is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.