Vacation Rentals in Montecalvario, Castellina in Chianti: Compare 10+ Sites & Save

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  2. Vacation Rentals
  3.  Italy
  4.  Tuscany
  5.  Castellina in Chianti
  6.  Montecalvario

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1083 Best Vacation Rentals in Montecalvario (Starting from $100)

Chianti Classico Home Panoramic View
Chianti Classico Home Panoramic View
House
Castellina in Chianti, Italy
0.2k from Montecalvario center

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

9 Bedrooms18 Guests
8.0

Good

5 reviews

$450
Average price / night
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ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Villa
Castellina in Chianti, 53011, Italy
0.0k from Montecalvario center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

11 Bedrooms23 Guests
10.0

Exceptional

64 reviews

$3564
Average price / night
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Casa Anna
Casa Anna
House
Castellina in Chianti, Italy
0.3k from Montecalvario center

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

3 Bedrooms4 Guests
8.9

Fabulous

7 reviews

$103
Average price / night
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Chianti Classico Home Panoramic View 8, Castellina in Chianti, Italy
Chianti Classico Home Panoramic View 8, Castellina in Chianti, Italy
House
Castellina in Chianti, 53011, Italy
0.2k from Montecalvario center

Dryer, Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$444
Average price / night
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Chianti Classico Home Panoramic View 4, Castellina in Chianti, Italy
Chianti Classico Home Panoramic View 4, Castellina in Chianti, Italy
House
Castellina in Chianti, 53011, Italy
0.2k from Montecalvario center

Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, TV

2 Bedrooms4 Guests
New to Booking
$233
Average price / night
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Casa Vacanze Squarcialupi
Casa Vacanze Squarcialupi
Apartment
Castellina in Chianti, Italy
0.3k from Montecalvario center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

10 Bedrooms16 Guests
9.3

Superb

284 reviews

$143
Average price / night
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Chianti Classico Home Panoramic View 6, Castellina in Chianti, Italy
Chianti Classico Home Panoramic View 6, Castellina in Chianti, Italy
House
Castellina in Chianti, 53011, Italy
0.2k from Montecalvario center

Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, TV

3 Bedrooms6 Guests
New to Booking
$338
Average price / night
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Palazzo Bianciardi Attico
Palazzo Bianciardi Attico
Apartment
Castellina in Chianti, Italy
0.3k from Montecalvario center

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

2 Bedrooms5 Guests
9.4

Superb

43 reviews

$158
Average price / night
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Mariani Bed & Breakfast
Mariani Bed & Breakfast
House
Viale della Rimembranza 70, Castellina in Chianti, 53011, Italy
0.4k from Montecalvario center

Free Parking, Heater, Housekeeping, Internet, No Smoking, Outdoor Space, Soundproof Room

9.8

Exceptional

17 reviews

$100
Average price / night
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Holiday Home Casa Chiara by Interhome
Holiday Home Casa Chiara by Interhome
House
Castellina in Chianti, Italy
0.5k from Montecalvario center

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

2 Bedrooms4 Guests
7.4

Good

5 reviews

$148
Average price / night
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Podere Palazzolo (ADULTS ONLY)
Podere Palazzolo (ADULTS ONLY)
House
Montecalvario, Castellina in Chianti, Tuscany, Italy
0.7k from Montecalvario center

Cheap, Accommodations, Pools, Parking, Country houses, Romantic, Cottages, Lodgings, Vacation rentals

13 Bedrooms26 Guests
8.9

Fabulous

157 reviews

$117
Average price / night
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Casa Chiara by Interhome
Casa Chiara by Interhome
House
Castellina in Chianti, 53011, Italy
0.5k from Montecalvario center

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

2 Bedrooms4 Guests
8.0

Good

1 reviews

$146
Average price / night
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Holiday Home Olivo by Interhome
Holiday Home Olivo by Interhome
House
Castellina in Chianti, Italy
0.7k from Montecalvario center

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

3 Bedrooms4 Guests
New to Booking
$291
Average price / night
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detached villa with private pool and garden
detached villa with private pool and garden
House
Castellina in Chianti, 53011, Italy
0.6k from Montecalvario center

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

3 Bedrooms4 Guests
8.8

Fabulous

26 reviews

$190
Average price / night
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Capanna Leopoldina 10
Capanna Leopoldina 10
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$707
Average price / night
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The Terrace
The Terrace
Apartment
Castellina in Chianti, 53011, Italy
0.6k from Montecalvario center

AC, Balcony, Barbecue, Internet, Kitchen, Laundry, No Smoking, Washer

1 Bedroom3 Guests
New to Booking
$164
Average price / night
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Il Nocino
Il Nocino
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$216
Average price / night
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Wonderful private villa for 14 guests with A/C, WIFI, private pool, TV, patio and panoramic view
Wonderful private villa for 14 guests with A/C, WIFI, private pool, TV, patio and panoramic view
Villa
Castellina In Chianti, 53011, Italy
0.7k from Montecalvario center

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

7 Bedrooms14 Guests
New to Booking
$804
Average price / night
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Capanna Leopoldina 8
Capanna Leopoldina 8
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$449
Average price / night
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Capanna Leopoldina 10, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Capanna Leopoldina 10, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Apartment
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Fireplace, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
New to Booking
$592
Average price / night
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La Querce
La Querce
Apartment
Castellina in Chianti, Italy
0.7k from Montecalvario center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay

2 Bedrooms3 Guests
10.0

Exceptional

2 reviews

$190
Average price / night
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Capanna Leopoldina 8, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Capanna Leopoldina 8, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Apartment
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Fireplace, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

4 Bedrooms8 Guests
New to Booking
$411
Average price / night
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Holiday Home Cerretino Tettoia by Interhome
Holiday Home Cerretino Tettoia by Interhome
House
Italy
0.8k from Montecalvario center

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

2 Bedrooms4 Guests
7.0

Good

1 reviews

$182
Average price / night
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Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Apartment
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space, Pool

2 Bedrooms4 Guests
New to Booking
$185
Average price / night
Check Availability
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
Apartment
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space, Pool

2 Bedrooms3 Guests
8.0

Good

1 reviews

$134
Average price / night
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Agriturismo La Ferrozzola
Agriturismo La Ferrozzola
House
Loc. Ferrozzola, 1, Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.4

Superb

9 reviews

$143
Average price / night
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Vacation home Olivo by Interhome
Vacation home Olivo by Interhome
House
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.6

Exceptional

4 reviews

$249
Average price / night
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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 Montecalvario.

Where to stay in Montecalvario? Best neighborhoods & areas

Montecalvario Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1083 verified vacation rentals in Montecalvario. 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 Montecalvario vary depending on the season, property size, and location. Rates typically start from around $100 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 Montecalvario 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 Montecalvario welcome pets. Currently, 37 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 Montecalvario often include amenities such as Internet, Fireplace/Heating, and Laundry. 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.