Vacation Rentals in Brotherhood Winery, NY: Compare 10+ Sites & Save

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47 Best Vacation Rentals in Brotherhood Winery (Starting from $119)

Estate with pool on 11 beautiful acres
Estate with pool on 11 beautiful acres
House
Monroe, NY, USA
4.2k from Brotherhood Winery center

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

9 Bedrooms24 Guests
New to Booking
$1758
Average price / night
Check Availability
Spacious 7BR Villa on 14 Acres w/ Indoor Pool
Spacious 7BR Villa on 14 Acres w/ Indoor Pool
House
Washingtonville, NY, 10992, United States
3.0k from Brotherhood Winery center

AC, Crib, Fireplace, Free Parking, Heater, Internet, Laundry, Living Area, Microwave

6 Bedrooms16 Guests
New to Booking
$1188
Average price / night
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Stunning, Private House in the Hills - Extra calm!
Stunning, Private House in the Hills - Extra calm!
Villa
Monroe, NY, USA
4.5k from Brotherhood Winery center

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

5 Bedrooms14 Guests
New to Booking
$754
Average price / night
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Cozy Lake Front House w. Pool near Storm King and West Point
Cozy Lake Front House w. Pool near Storm King and West Point
House
Beaverdam Lake-Salisbury Mills, NY, 12577, United States
3.4k from Brotherhood Winery center

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

4 Bedrooms10 Guests
8.0

Good

2 reviews

$855
Average price / night
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Secluded Sanctuary in Nature
Secluded Sanctuary in Nature
House
Monroe, NY, USA
4.7k from Brotherhood Winery center

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

6 Bedrooms16 Guests
New to Booking
$839
Average price / night
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Spacious 9-bedroom house in tranquil Monroe with AC
Spacious 9-bedroom house in tranquil Monroe with AC
House
Monroe, NY, 10950, United States
3.8k from Brotherhood Winery center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

9 Bedrooms32 Guests
New to Booking
$1915
Average price / night
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1 Bedroom 15 min from Stewart airport
1 Bedroom 15 min from Stewart airport
Apartment
Brotherhood Winery, Washingtonville, New York, USA
4.8k from Brotherhood Winery center

Internet, Parking, Laundry, Air Conditioner

1 Bedroom2 Guests
5.0

Review score

2 reviews

$119
Average price / night
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Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall
Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall
House
Campbell Hall, NY, 10916, United States
4.0k from Brotherhood Winery center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, TV

4 Bedrooms8 Guests
New to Booking
$443
Average price / night
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Very Private Large Home on 22 Acres
Very Private Large Home on 22 Acres
House
Chester, NY, USA
6.3k from Brotherhood Winery center

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

5 Bedrooms14 Guests
New to Booking
$913
Average price / night
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Upstate NY getaway- View, Pool, Close to Woodbury Common
Upstate NY getaway- View, Pool, Close to Woodbury Common
House
Monroe, NY, 10950, United States
4.0k from Brotherhood Winery center

AC, Internet, Pool

2 Bedrooms8 Guests
New to Booking
$269
Average price / night
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A Restored Schoolhouse With Movie Theater, Firepit, and Pool
A Restored Schoolhouse With Movie Theater, Firepit, and Pool
House
Rock Tavern, NY, 12575, United States
4.2k from Brotherhood Winery center

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

4 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$567
Average price / night
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Incredible Ranch in the Woods - Peace and Luxury!
Incredible Ranch in the Woods - Peace and Luxury!
House
Brotherhood Winery, Washingtonville, New York, USA
7.1k from Brotherhood Winery center

Internet, Pool, Air Conditioner, Parking, Pet Friendly, Child Friendly

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$309
Average price / night
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Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Villa
Monroe, NY, 10950, United States
4.3k from Brotherhood Winery center

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

3 Bedrooms10 Guests
7.4

Good

3 reviews

$485
Average price / night
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Malkita Terra -Earthly Elegance
Malkita Terra -Earthly Elegance
Villa
Woodbury, NY, USA
7.7k from Brotherhood Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

6 Bedrooms15 Guests
New to Booking
$995
Average price / night
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Cozy Getaway on a 50 Acre Historic Ranch
Cozy Getaway on a 50 Acre Historic Ranch
House
Beaverdam Lake-Salisbury Mills, NY, 12577, United States
4.3k from Brotherhood Winery center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$334
Average price / night
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Malkita Aria Mountainview Retreat
Malkita Aria Mountainview Retreat
Villa
Brotherhood Winery, Washingtonville, New York, USA
7.7k from Brotherhood Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms8 Guests
8.2

Very Good

5 reviews

$1045
Average price / night
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Studio Retreat | Near Woodbury Commons & Legoland
Studio Retreat | Near Woodbury Commons & Legoland
Apartment
Monroe, NY, 10950, United States
4.7k from Brotherhood Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, No Smoking, Outdoor Space, TV

New to Booking
$234
Average price / night
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Bright Studio Retreat w/ Deck & Nature Views
Bright Studio Retreat w/ Deck & Nature Views
Apartment
Monroe, NY, 10950, United States
4.7k from Brotherhood Winery center

AC, Balcony, Free Parking, Heater, Internet, No Smoking, Outdoor Space, TV

New to Booking
$122
Average price / night
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Rustic Lakefront Studio w/ Deck + Workspace
Rustic Lakefront Studio w/ Deck + Workspace
Apartment
Monroe, NY, 10950, United States
4.7k from Brotherhood Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, No Smoking, Outdoor Space, TV

8.0

Good

1 reviews

$240
Average price / night
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Rustic Lakefront Studio with Deck & Workspace
Rustic Lakefront Studio with Deck & Workspace
Apartment
Monroe, NY, 10950, United States
4.7k from Brotherhood Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, No Smoking, Outdoor Space, TV

New to Booking
$234
Average price / night
Check Availability
Cozy Modern Studio Near Lake • Porch & Fire Pit
Cozy Modern Studio Near Lake • Porch & Fire Pit
Apartment
Monroe, NY, 10950, United States
4.7k from Brotherhood Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, No Smoking, Outdoor Space, TV

New to Booking
$241
Average price / night
Check Availability
Third floor apartment with a shared backyard
Third floor apartment with a shared backyard
Cabin
Monroe, NY, 10950, United States
4.9k from Brotherhood Winery center

Internet, No Smoking

1 Bedroom6 Guests
New to Booking
$1131
Average price / night
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Cozy Cabin with Sauna & Firepit!
Cozy Cabin with Sauna & Firepit!
House
Monroe, NY, 10950, United States
5.1k from Brotherhood Winery center

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

3 Bedrooms6 Guests
9.0

Fabulous

43 reviews

$218
Average price / night
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Woodland Sanctuary - 6000ft retreat for pure relaxation!
Woodland Sanctuary - 6000ft retreat for pure relaxation!
House
New Windsor, NY, 12553, United States
5.5k from Brotherhood Winery center

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

7 Bedrooms18 Guests
New to Booking
$1590
Average price / night
Check Availability
Family Staycation Retreat 7BDR.Sauna.Games.Gym
Family Staycation Retreat 7BDR.Sauna.Games.Gym
House
Campbell hall, NY, 10916, United States
5.6k from Brotherhood Winery center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

7 Bedrooms24 Guests
New to Booking
$1979
Average price / night
Check Availability
Private 5-Bed Country Estate on 22 Acres
Private 5-Bed Country Estate on 22 Acres
House
Chester, NY, 10918, United States
6.5k from Brotherhood Winery center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Laundry, Living Area, Microwave

5 Bedrooms12 Guests
New to Booking
$961
Average price / night
Check Availability
Hudson Valley Oasis - Hot Tub, Fireplace, 50mi NYC
Hudson Valley Oasis - Hot Tub, Fireplace, 50mi NYC
House
New Windsor, NY, 12553, United States
6.7k from Brotherhood Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$1352
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 Brotherhood Winery.

Brotherhood Winery Vacation Rentals on the Map

Frequently Asked Questions

You can explore 47 verified vacation rentals in Brotherhood Winery. 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 Brotherhood Winery vary depending on the season, property size, and location. Rates typically start from around $119 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 Brotherhood Winery 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 Brotherhood Winery welcome pets. Currently, 29 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 Brotherhood Winery often include amenities such as Fireplace/Heating, Pet Friendly, and Kitchen. 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.