Short-Term Rentals in Sugar Loaf, NY: Compare 10+ Sites & Save

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86 Best Short-Term Rentals in Sugar Loaf (Starting from $148)

Millionare Mansion with Grill, Spa, Huge Deck,Views, Game Room, Hiking, More
Millionare Mansion with Grill, Spa, Huge Deck,Views, Game Room, Hiking, More
Apartment
Chester, NY, USA
2.8k from Sugar Loaf center

Child Friendly, Parking, Kitchen, Breakfast, Balcony/Terrace, Internet, Smoking

4 Bedrooms10 Guests
New to Booking
$894
Average price / night
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Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Apartment
Chester, NY, 10918, United States
0.1k from Sugar Loaf center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms6 Guests
10.0

Exceptional

55 reviews

$229
Average price / night
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Craftsman Hideaway at the 1841 Farmhouse
Craftsman Hideaway at the 1841 Farmhouse
Apartment
Chester, NY, USA
2.8k from Sugar Loaf center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom2 Guests
9.2

Superb

5 reviews

$229
Average price / night
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Charming 1-bedroom Rekindled  Farmhouse Historic Sugar Loaf, NY
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY
Apartment
Chester, NY, 10918, United States
0.6k from Sugar Loaf center

AC, Heater, Internet, No Smoking

1 Bedroom4 Guests
9.8

Exceptional

8 reviews

$196
Average price / night
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1786 Farm Cottage Honeymoon Suite Renovated 2022
1786 Farm Cottage Honeymoon Suite Renovated 2022
House
Chester, NY, USA
2.8k from Sugar Loaf center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
9.0

Fabulous

6 reviews

$229
Average price / night
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Great country getaway near skiing!
Great country getaway near skiing!
House
Chester, NY, 10918, United States
2.8k from Sugar Loaf center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
New to Booking
$518
Average price / night
Check Availability
Elegant Home 7BRs, Game Room, Luxury Yard, Pool
Elegant Home 7BRs, Game Room, Luxury Yard, Pool
Apartment
Chester, NY, USA
4.2k from Sugar Loaf center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

2 Bedrooms16 Guests
New to Booking
$882
Average price / night
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Cozy studio on 36 acres close to everything in Warwick
Cozy studio on 36 acres close to everything in Warwick
Apartment
Chester, NY, 10918, United States
2.8k from Sugar Loaf center

AC, Fireplace, Free Parking, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$201
Average price / night
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Hudson Valley Retreat with Pool Near Greenwood Lake
Hudson Valley Retreat with Pool Near Greenwood Lake
House
Monroe, NY, USA
4.7k from Sugar Loaf center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$387
Average price / night
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Cozy cottage, beautiful views, close to Warwick!
Cozy cottage, beautiful views, close to Warwick!
House
Chester, NY, 10918, United States
2.8k from Sugar Loaf center

AC, Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Living Area, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$252
Average price / night
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Family Home Close to Warwick, 5 Mi to Lake!
Family Home Close to Warwick, 5 Mi to Lake!
House
Monroe, NY, USA
5.3k from Sugar Loaf center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay

4 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$492
Average price / night
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Spacious 5-bedroom house in serene Chester perfect for families
Spacious 5-bedroom house in serene Chester perfect for families
House
Chester, NY, 10918, United States
3.1k from Sugar Loaf center

AC, Fitness Equipment, Heater, Internet, No Smoking

5 Bedrooms14 Guests
New to Booking
$727
Average price / night
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Relaxing New York Home with Boat Dock and Lake View!
Relaxing New York Home with Boat Dock and Lake View!
House
Monroe, NY, USA
5.3k from Sugar Loaf center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms6 Guests
7.5

Good

2 reviews

$289
Average price / night
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Chic 2-bedroom apartment with WiFi, AC in charming Warwick
Chic 2-bedroom apartment with WiFi, AC in charming Warwick
Apartment
Warwick, NY, 10990, United States
3.7k from Sugar Loaf center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking, Washer

2 Bedrooms5 Guests
New to Booking
$219
Average price / night
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Walton Lake Mountain Lodge
Walton Lake Mountain Lodge
House
Monroe, NY, USA
5.4k from Sugar Loaf center

Laundry, Wheelchair Accessible, Pool, Hot Tub, Parking, Internet, Child Friendly

4 Bedrooms10 Guests
New to Booking
$498
Average price / night
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Summerville Getaway (30 min to Mt. Creek)
Summerville Getaway (30 min to Mt. Creek)
House
Chester, NY, 10918, United States
4.0k from Sugar Loaf center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

7 Bedrooms14 Guests
9.8

Exceptional

18 reviews

$982
Average price / night
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KW homes
KW homes
House
NY, USA
6.2k from Sugar Loaf center

B&bs, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms10 Guests
New to Booking
$374
Average price / night
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Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
House
Chester, NY, 10918, United States
4.1k from Sugar Loaf center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

7 Bedrooms16 Guests
9.0

Fabulous

2 reviews

$845
Average price / night
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Spacious Home Pool Hot Tub, Mins to Parks
Spacious Home Pool Hot Tub, Mins to Parks
Apartment
Monroe, NY, USA
6.9k from Sugar Loaf center

Air Conditioner, Parking, Security/Safety, View, Pool, Internet, Barbecue/Outdoor Cooking

2 Bedrooms8 Guests
New to Booking
$1800
Average price / night
Check Availability
Spacious Suite (1 hr to Manhattan)
Spacious Suite (1 hr to Manhattan)
House
Chester, NY, 10918, United States
4.2k from Sugar Loaf center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.6

Exceptional

8 reviews

$203
Average price / night
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Spacious Home with Pool, Hot Tub, Mins to Parks Skiing
Spacious Home with Pool, Hot Tub, Mins to Parks Skiing
Apartment
Monroe, NY, USA
6.9k from Sugar Loaf center

Business Services, Air Conditioner, Fireplace/Heating, Child Friendly, Security/Safety, Pool, Barbecue/Outdoor Cooking

1 Bedroom8 Guests
10.0

Exceptional

2 reviews

$548
Average price / night
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Guesthouse 2 bedroom. 25min-West Point
Guesthouse 2 bedroom. 25min-West Point
House
Chester, NY, 10918, United States
4.2k from Sugar Loaf center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$183
Average price / night
Check Availability
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cottage
Monroe, NY, 10950, United States
4.7k from Sugar Loaf center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$271
Average price / night
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Modern Comfort Timeless Charm - Log Cabin Retreat
Modern Comfort Timeless Charm - Log Cabin Retreat
House
Warwick, NY, 10990, United States
4.8k from Sugar Loaf center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$690
Average price / night
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Amazing  Home Near West Point,  Shopping,  Skiing and Legoland
Amazing Home Near West Point, Shopping, Skiing and Legoland
House
Monroe, NY, 10950, United States
4.8k from Sugar Loaf center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms9 Guests
10.0

Exceptional

14 reviews

$593
Average price / night
Check Availability
Spacious 4-bedroom house in awesome Monroe with cool comfort
Spacious 4-bedroom house in awesome Monroe with cool comfort
House
Monroe, NY, 10950, United States
4.9k from Sugar Loaf center

AC, Fitness Equipment, Heater, Laundry

4 Bedrooms6 Guests
New to Booking
$556
Average price / night
Check Availability
Charming  house surrounded lakes and the fresh air of the mountains
Charming house surrounded lakes and the fresh air of the mountains
House
Monroe, NY, 10950, United States
5.2k from Sugar Loaf center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

1 Bedroom6 Guests
9.6

Exceptional

19 reviews

$148
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Sugar Loaf.

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Sugar Loaf Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 86 verified short-term rentals in Sugar Loaf, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Sugar Loaf vary depending on location, property size, and travel dates. Rates typically start from around $148 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Sugar Loaf include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Sugar Loaf, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Sugar Loaf often include amenities such as Fireplace/Heating, Wellness Facilities, and Child Friendly, providing a comfortable and convenient stay.

Short-term rentals in Sugar Loaf are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.