Vacation Rentals in Furnace Brook Winery at Hilltop Orchards, MA: Compare 10+ Sites & Save

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132 Best Vacation Rentals in Furnace Brook Winery at Hilltop Orchards (Starting from $140)

1 Mi to Vineyard Serene Berkshires Country Escape
1 Mi to Vineyard Serene Berkshires Country Escape
House
Richmond, MA, USA
1.5k from Furnace Brook Winery at Hilltop Orchards center

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

1 Bedroom7 Guests
New to Booking
$497
Average price / night
Check Availability
Morning Face - Berkshire estate with heated pool, views and privacy.
Morning Face - Berkshire estate with heated pool, views and privacy.
House
Richmond, MA, 01254, United States
1.0k from Furnace Brook Winery at Hilltop Orchards center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$1583
Average price / night
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Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature
Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature
House
Canaan, NY, USA
2.2k from Furnace Brook Winery at Hilltop Orchards center

Parking, Fireplace/Heating, Security/Safety, View, Internet, Air Conditioner

2 Bedrooms6 Guests
9.3

Superb

3 reviews

$326
Average price / night
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Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood
Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood
House
Richmond, MA, 01254, United States
1.4k from Furnace Brook Winery at Hilltop Orchards center

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

4 Bedrooms7 Guests
9.4

Superb

3 reviews

$449
Average price / night
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Berkshire Cottage in Gorgeous Setting!
Berkshire Cottage in Gorgeous Setting!
House
Richmond, MA, USA
4.6k from Furnace Brook Winery at Hilltop Orchards center

Parking, Air Conditioner, Internet

2 Bedrooms4 Guests
New to Booking
$223
Average price / night
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6 Mi to Tanglewood Peaceful Berkshire Apt!
6 Mi to Tanglewood Peaceful Berkshire Apt!
Apartment
Richmond, MA, USA
4.6k from Furnace Brook Winery at Hilltop Orchards center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$300
Average price / night
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Cozy 3-bedroom chalet with mountain views
Cozy 3-bedroom chalet with mountain views
Ski Chalet
Canaan, NY, 12029, United States
2.6k from Furnace Brook Winery at Hilltop Orchards center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$140
Average price / night
Check Availability
Wellspring by AvantStay Indoor Pool Views
Wellspring by AvantStay Indoor Pool Views
House
Richmond, MA, USA
5.9k from Furnace Brook Winery at Hilltop Orchards center

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

1 Bedroom12 Guests
New to Booking
$960
Average price / night
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Private home on a Beautiful lake. Large deck for entertaining
Private home on a Beautiful lake. Large deck for entertaining
House
Canaan, NY, 12029, United States
2.8k from Furnace Brook Winery at Hilltop Orchards center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

5 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$486
Average price / night
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Historic New Lebanon Hideaway on 33 Private Acres!
Historic New Lebanon Hideaway on 33 Private Acres!
House
NY, USA
6.9k from Furnace Brook Winery at Hilltop Orchards center

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

5 Bedrooms10 Guests
8.0

Good

2 reviews

$623
Average price / night
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Berkshire Lake House Private Dock Sleeps 6
Berkshire Lake House Private Dock Sleeps 6
Cottage
Canaan, NY, 12029, United States
3.0k from Furnace Brook Winery at Hilltop Orchards center

AC, Heater, Internet, No Smoking

3 Bedrooms6 Guests
New to Booking
$294
Average price / night
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Stunning All-Season Renovated Barn Escape!
Stunning All-Season Renovated Barn Escape!
Villa
East Chatham, NY, USA
9.0k from Furnace Brook Winery at Hilltop Orchards center

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

2 Bedrooms5 Guests
New to Booking
$200
Average price / night
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Cozy cabin in tranquil Canaan NY with WiFi, AC
Cozy cabin in tranquil Canaan NY with WiFi, AC
Cabin
Canaan, NY, 12029, United States
3.1k from Furnace Brook Winery at Hilltop Orchards center

AC, Heater, Internet, No Smoking

1 Bedroom3 Guests
New to Booking
$235
Average price / night
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Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
House
Lenox, MA, USA
9.1k from Furnace Brook Winery at Hilltop Orchards center

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

3 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$253
Average price / night
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Secluded Mountain and Lake View in Canaan, NY
Secluded Mountain and Lake View in Canaan, NY
House
Canaan, NY, 12029, United States
3.3k from Furnace Brook Winery at Hilltop Orchards center

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

3 Bedrooms6 Guests
New to Booking
$459
Average price / night
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Stockbridge Home Walk to Town Beach!
Stockbridge Home Walk to Town Beach!
House
Stockbridge, MA, USA
9.1k from Furnace Brook Winery at Hilltop Orchards center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
8.3

Very Good

3 reviews

$492
Average price / night
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Berkshires Lake House, gunite pool,  and Chefs Kitchen
Berkshires Lake House, gunite pool, and Chefs Kitchen
House
Canaan, NY, 12029, United States
3.4k from Furnace Brook Winery at Hilltop Orchards center

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

6 Bedrooms10 Guests
9.8

Exceptional

47 reviews

$1065
Average price / night
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Urban Peak Escape
Urban Peak Escape
Apartment
Lenox, MA, USA
9.2k from Furnace Brook Winery at Hilltop Orchards center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$585
Average price / night
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Best of the Berkshires & Hudson Valley
Best of the Berkshires & Hudson Valley
Apartment
Canaan, NY, 12029, United States
3.5k from Furnace Brook Winery at Hilltop Orchards center

Kitchen, Microwave, No Smoking, Patio, Toys, TV

10.0

Exceptional

1 reviews

$195
Average price / night
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Walk to Dining Downtown Lenox Guest House!
Walk to Dining Downtown Lenox Guest House!
House
Lenox, MA, USA
9.4k from Furnace Brook Winery at Hilltop Orchards center

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

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$217
Average price / night
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Private apartment in beautiful country barn
Private apartment in beautiful country barn
Apartment
Richmond, MA, 01201, United States
3.6k from Furnace Brook Winery at Hilltop Orchards center

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

1 Bedroom4 Guests
10.0

Exceptional

23 reviews

$202
Average price / night
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Restored 1881 Farm House
Restored 1881 Farm House
House
Furnace Brook Winery at Hilltop Orchards, Richmond, Massachusetts, USA
9.6k from Furnace Brook Winery at Hilltop Orchards center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms4 Guests
9.5

Superb

2 reviews

$399
Average price / night
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Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
House
Richmond, MA, 01254, United States
3.8k from Furnace Brook Winery at Hilltop Orchards center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

12 reviews

$718
Average price / night
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New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Apartment
Richmond, MA, 01254, United States
3.8k from Furnace Brook Winery at Hilltop Orchards center

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

2 Bedrooms7 Guests
10.0

Exceptional

12 reviews

$325
Average price / night
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Berkshires Colonial on 2 Acres by Evergreen Home
Berkshires Colonial on 2 Acres by Evergreen Home
House
Pittsfield, MA, 01201, United States
3.9k from Furnace Brook Winery at Hilltop Orchards center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$458
Average price / night
Check Availability
Beautiful, cozy 2-bedroom cottage in charming Canaan perfect for a long getaway
Beautiful, cozy 2-bedroom cottage in charming Canaan perfect for a long getaway
Cottage
Canaan, NY, 12029, United States
4.1k from Furnace Brook Winery at Hilltop Orchards center

Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Living Area, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$229
Average price / night
Check Availability
Family Fun in The Berkshires at Beautiful Hygge House
Family Fun in The Berkshires at Beautiful Hygge House
House
Pittsfield, MA, 01201, United States
4.3k from Furnace Brook Winery at Hilltop Orchards center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$526
Average price / night
Check Availability

Other accommodation types in Furnace Brook Winery at Hilltop Orchards:

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 Furnace Brook Winery at Hilltop Orchards.

Furnace Brook Winery at Hilltop Orchards Vacation Rentals on the Map

Frequently Asked Questions

You can explore 132 verified vacation rentals in Furnace Brook Winery at Hilltop Orchards. 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 Furnace Brook Winery at Hilltop Orchards vary depending on the season, property size, and location. Rates typically start from around $140 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 Furnace Brook Winery at Hilltop Orchards 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 Furnace Brook Winery at Hilltop Orchards welcome pets. Currently, 23 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 Furnace Brook Winery at Hilltop Orchards often include amenities such as Fireplace/Heating, Internet, 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.