My Dreamy Destination - Vacation Rentals in Castellina in Chianti

Strada di Tregole Cottage From US $99
         

8.5 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Il Nespolo Charming Apartment Fonterutoli From US $288
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Farmhouse in the heart of the real chiantishire From US $180
         

10.0 (153 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Castellina in Chianti

Over 449+ Luxury Places to Stay in or Near Castellina in Chianti

Top-Rated Vacation Rentals with a Pool in Castellina in Chianti

Over 341+ Top-Rated Vacation Rentals with a Pool in or Near Castellina in Chianti
Castello La Leccia From US $411
         

10.0 (103 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Castellina in Chianti

Over 228+ Pet-Friendly Vacation Rentals in or Near Castellina in Chianti
Private villa in the heart of chianti with view of siena From US $608
         

10.0 (5 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Villa La Canonica Di Pietrafitta From US $854
         

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10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
Riserva di Fizzano Residence From US $206
         

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9.6 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Villa in Chianti with Winery up to 10pax From US $1,891
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Tregole by MMega From US $948
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Castellina in Chianti

Over 159+ Large Vacation Homes & Villas in or Near Castellina in Chianti
Villa in San Leonino with 6 bedrooms sleeps 12 From US $995
         

10.0 (28 Reviews)
Villa
  • Parking
  • Pool
  • Designated Smoking Area
Molino di Cogno From US $193
         

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10.0 (48 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Villa in Castellina w Pool Garden Winery From US $1,636
         

New
Villa
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
Casa Fioraie - House with private pool From US $517
         

Casale Il Poggino by Interhome From US $1,204
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Castellina in Chianti

Over 16+ Wheelchair Accessible Vacation Homes in or Near Castellina in Chianti
Appartamento 510 From US $194
         

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New
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Palazzo Squarcialupi From US $253
         

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9.8 (73 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Appartamento 503 From US $133
         

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New
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Hotel Casafrassi Wine Resort From US $145
         

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8.2 (215 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Gran Sogno From US $312
         

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9.9 (15 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Castello La Leccia From US $348
         

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9.7 (335 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Relais Riserva di Fizzano From US $225
         

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9.3 (424 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Borgo Sicelle Residence From US $87
         

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9.3 (72 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Castellina in Chianti Vacation Rentals and Airbnb Places to Stay Under $200

Over 174+ Castellina in Chianti Vacation Rentals and Airbnb Places to Stay Under $200
Casa Bruna - Cipresseta del Chianti From US $122
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Il Rustico From US $84
         

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9.0 (21 Reviews)
Apartment
  • Parking
  • Pool
  • Balcony/Terrace
Borgo Sicelle From US $88
         

9.8 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
LAURO apartment kitchen, garden From US $147
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Castellina in Chianti

Over 179+ Instantly Bookable Vacation Homes in or Near Castellina in Chianti
Tuscany. Lovely holiday home with swimming pool. From US $219
         

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL From US $387
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

About Castellina in Chianti Vacation Rentals

With more than 458 Castellina in Chianti vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Mydreamydestination and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Castellina in Chianti.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Mydreamydestination Castellina in Chianti, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Castellina in Chianti. Places to stay near Castellina in Chianti are 1680.78 ft² on average, with prices averaging US $509 a night.

Mydreamydestination makes it easy and safe to find and compare vacation rentals in Castellina in Chianti with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Castellina in Chianti

Type Count
Vacation Homes 146
Holiday Apartments 138
Villas 116
Others 18
Hotels 16
Cottages 12
B&B 11
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Castellina in Chianti

Pro Tip: Mydreamydestination makes it easy to compare the best listings on Mydreamydestination homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Mydreamydestination homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Castellina in Chianti.

Weather in Castellina in Chianti

View the weather forecast for Castellina in Chianti before booking your Castellina in Chianti Vacation Rentals to confirm your best time to go.

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Castellina in Chianti Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Castellina in Chianti?
How many vacation rentals are available in Castellina in Chianti?

Currently, the total number of properties listed in 2026 is over 458 in the Castellina in Chianti area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Castellina in Chianti.