Sugar Loaf Vacation Rentals

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Check prices for these dates

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

Vacation 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 ￥14,458
￥29,332 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥13,924
￥42,556 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥16,947
￥66,927 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥13,924
￥36,366 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥22,878
￥45,073 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥24,204
￥43,668 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥22,897
￥65,246 total
includes taxes & fees
Nov 23 - Nov 24
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 ￥17,018
￥38,195 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥12,756
￥22,798 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥16,484
￥37,818 total
includes taxes & fees
Nov 17 - Nov 18
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Apartment (1 Bedroom) | Interior
Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex

3.0 star property
Newburgh
The price is ￥25,063
￥47,587 total
includes taxes & fees
Nov 14 - Nov 15
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 ￥28,753
￥54,466 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥28,809
￥50,541 total
includes taxes & fees
Nov 24 - Nov 25
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 ￥17,544
￥30,349 total
includes taxes & fees
Dec 7 - Dec 8
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 ￥27,848
￥68,082 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥20,798
￥36,395 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥20,112
￥68,139 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥26,479
￥50,247 total
includes taxes & fees
Dec 10 - Dec 11
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 ￥15,873
￥39,951 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥19,258
￥41,244 total
includes taxes & fees
Nov 17 - Nov 18
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.
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Top Sugar Loaf Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Clean and quiet room. Staff was super friendly. Breakfast was nice. No complaints at all! We traveled with an infant and toddler and they even put us in an end room, which was thoughtful. If the kids made noise I didn’t worry so much about them disturbing other guests. We will definitely stay there again. "
Caitlin 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Find out more about Sugar Loaf

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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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Sugar Loaf is located on a lake and has a patio, a garden, and a barbecue grill 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 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.