Vacation Rentals in Sugar Loaf, NY: Compare 10+ Sites & Save

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92 Best Vacation Rentals in Sugar Loaf (Starting from $183)

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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Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Villa
Chester, NY, 10918, United States
2.8k from Sugar Loaf center

AC, Arcade, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

7 Bedrooms16 Guests
9.6

Exceptional

13 reviews

$1676
Average price / night
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Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Villa
Chester, NY, USA
3.8k from Sugar Loaf center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis

9 Bedrooms28 Guests
New to Booking
$1991
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
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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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Huge Retreat w Alaska King, Pool & Jacuzzi Tub Indoor
Huge Retreat w Alaska King, Pool & Jacuzzi Tub Indoor
Villa
Goshen, NY, USA
4.5k from Sugar Loaf center

Air Conditioner, Parking, Pet Friendly, Internet, Pool, Balcony/Terrace, Security/Safety

1 Bedroom13 Guests
New to Booking
$789
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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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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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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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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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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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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Grand 10BR Retreat w/Pool & Hot Tub
Grand 10BR Retreat w/Pool & Hot Tub
Villa
Chester, NY, 10918, United States
4.0k from Sugar Loaf center

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

10 Bedrooms23 Guests
2.0

Review score

1 reviews

$2210
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 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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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
Check Availability
11BR Retreat w Pool & Game Room
11BR Retreat w Pool & Game Room
Villa
Chester, NY, 10918, United States
4.7k from Sugar Loaf center

AC, Arcade, Barbecue, Crib, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

11 Bedrooms28 Guests
New to Booking
$2617
Average price / night
Check Availability
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
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 Vacation Rentals in Sugar Loaf.

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Frequently Asked Questions

You can explore 92 verified vacation rentals in Sugar Loaf. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Sugar Loaf vary depending on the season, property size, and location. Rates typically start from around $183 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Sugar Loaf include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Sugar Loaf welcome pets. Currently, 26 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Sugar Loaf often include amenities such as Fireplace/Heating, Wellness Facilities, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.