Holiday Rentals in Sugar Loaf

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Holiday Rentals in Sugar Loaf

Gorgeous Garrison Gem Pool Sauna Hot Tub More

2.0 star property
The price is €1,365
includes taxes & fees
6 Jul - 7 Jul
Gorgeous Garrison Gem Pool Sauna Hot Tub More

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is €714
includes taxes & fees
6 Jul - 7 Jul
West Point Family Retreat, 5 min walk to Thayer!

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

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is €305
includes taxes & fees
1 Jul - 2 Jul
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is €378
includes taxes & fees
27 Jul - 28 Jul
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is €1,033
includes taxes & fees
17 Jul - 18 Jul
Room for Everyone: Spacious 6BR West Point Retreat

Woodland Sanctuary - 6000ft retreat for pure relaxation!

The price is €2,285
includes taxes & fees
11 Jul - 12 Jul
Woodland Sanctuary - 6000ft retreat for pure relaxation!

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (295)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is €513
includes taxes & fees
6 Jul - 7 Jul
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Mid-Hudson Estate on 11 acres with pool

10.0 out of 10, Exceptional, (6)
"We were pleased with every aspect of our stay. The property fully fulfilled all our needs. Highly recommended!"
The price is €5,800
includes taxes & fees
5 Jul - 6 Jul
Mid-Hudson Estate on 11 acres with pool

5BR Home with Sauna & Pool Hot tub Fire pit

The price is €1,237
includes taxes & fees
2 Jul - 3 Jul
5BR Home with Sauna & Pool Hot tub Fire pit

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is €1,097
includes taxes & fees
12 Jul - 13 Jul
The Perfect Essential Getaway!

Amazing Home Near West Point, Shopping, Skiing and Legoland

10.0 out of 10, Exceptional, (12)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
The price is €519
includes taxes & fees
1 Jul - 2 Jul
Amazing Home Near West Point, Shopping, Skiing and Legoland

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"The house was very clean and beautiful inside. Beds were incredibly comfortable, short distance to town and skiing at Mt Peter which was the reason for our visit. Spa was clean although we didn’t use it because there was a snow storm. Overall great visit!"
The price is €591
includes taxes & fees
9 Jul - 10 Jul
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

10.0 out of 10, Exceptional, (1)
"The location was fantastic and the place was amazing. Our family enjoyed the great views and the house had all the amenities to spend a relaxing vacation. "
The price is €661
includes taxes & fees
6 Jul - 7 Jul
Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck ~ Living Room

10.0 out of 10, Exceptional, (1)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
The price is €918
includes taxes & fees
30 Jun - 1 Jul
Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck ~ Living Room

Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub

9.8 out of 10, Exceptional, (8)
"Incredible place, scenic views, newly renovated house me and my family enjoyed it all! Besides that the host was very responsive and friendly."
The price is €1,522
includes taxes & fees
29 Jun - 30 Jun
Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub

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

2.0 star property
The price is €454
includes taxes & fees
8 Jul - 9 Jul
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

The price is €171
includes taxes & fees
14 Jul - 15 Jul
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had workers that were erecting a building nearby and needed a play to stay. Our workers had nothing but nice things to stay about the house and the property. They absolutely loved it and would stay again!"
Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (24)
"A beautiful and bright cottage in a serene but convenient location. It was thoughtfully set up for a family getaway and was exceptionally clean. My entire family enjoyed the stay!"
The price is €836
includes taxes & fees
30 Jun - 1 Jul
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Spectacular Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (9)
"We had a great time with our extended family at this beautiful house. The tennis court and swimming pool were great additions to our stay and vacation. Some minor issues arose, but the owner was incredibly responsive and moved to fix any issues quickly and successfully. Would stay again!"
The price is €2,963
includes taxes & fees
10 Jul - 11 Jul
Spectacular Mansion w/Pool&Tennis
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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Frequently asked questions

Can I find a holiday rental in Sugar Loaf?

Yes, there are holiday rentals where you'll be only 4.2 mi (6.7 km) from LEGOLAND® New York, giving you a more remote option if you want a quiet place to stay. Sugar Loaf is known for its shopping and restaurants.

What are some of the best holiday rentals that Sugar Loaf has to offer?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8: This holiday home rental outside of Sugar Loaf is located on a lake, and offers a BBQ, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 LEGOLAND® New York, or get outside and enjoy nature at The Rock Sports Complex. Woodbury Common Premium Outlets and Castle Fun Center 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.