Top Rated Activities & Tours in Castellina in Chianti

10
Excellent
56 Reviews
5 star rating Recommendation
From
US $504 Per Person
10
Excellent
23 Reviews
5 star rating Recommendation
From
US $389 Per Person
10
Excellent
11 Reviews
5 star rating Recommendation
From
US $376 Per Person
10
Excellent
5 Reviews
5 star rating Recommendation
From
US $399 Per Person

Trips to Castellina in Chianti

Plan Your Next Trip to Castellina in Chianti and explore unforgettable sights, local flavors, and exciting experiences.

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

Luxury Places to Stay in Castellina in Chianti

Over 444+ Luxury Places to Stay in or Near Castellina in Chianti

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

Over 339+ Top-Rated Vacation Rentals with a Pool in or Near Castellina in Chianti
Castello La Leccia From US $278
         

10.0 (100 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Castellina in Chianti

Over 219+ Pet-Friendly Vacation Rentals in or Near Castellina in Chianti
Farmhouse in the heart of the real chiantishire From US $181
         

10.0 (153 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa La Canonica Di Pietrafitta From US $854
         

|
10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
Riserva di Fizzano Residence From US $221
         

|
9.8 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private villa in the heart of chianti with view of siena From US $633
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Luxury Villa in Chianti with Winery up to 10pax From US $1,913
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa La Misura, garden and pool in the heart of Chianti From US $445
         

Villa Tregole by MMega From US $792
         

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

Large Vacation Homes & Villas in Castellina in Chianti

Over 155+ 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
         

|
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 $505
         

Casale Il Poggino by Interhome From US $734
         

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

Wheelchair Accessible Vacation Homes in Castellina in Chianti

Over 15+ Wheelchair Accessible Vacation Homes in or Near Castellina in Chianti
Appartamento 510 From US $194
         

|
New
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Palazzo Squarcialupi From US $212
         

|
9.8 (72 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Appartamento 503 From US $133
         

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

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

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

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

|
9.3 (423 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Borgo Sicelle Residence From US $87
         

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

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

Over 184+ Castellina in Chianti Vacation Rentals and Airbnb Places to Stay Under $200
Il Rustico From US $84
         

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

9.8 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Casa Bruna - Cipresseta del Chianti From US $119
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
LAURO apartment kitchen, garden From US $134
         

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

Instantly Bookable Vacation Homes in Castellina in Chianti

Over 174+ Instantly Bookable Vacation Homes in or Near Castellina in Chianti
Tuscany. Lovely holiday home with swimming pool. From US $216
         

About Castellina in Chianti Vacation Rentals

With more than 453 Castellina in Chianti vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Smartours 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 Smartours 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 1693.43 ft² on average, with prices averaging $491 a night.

Smartours 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 143
Holiday Apartments 137
Villas 116
Others 18
Hotels with Suites 16
B&B 11
Cottages 11
Resorts 1

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

Pro Tip: Smartours makes it easy to compare the best listings on Smartours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Smartours 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.

December - February
High       Low
March - May
High       Low
June - August
High       Low
September - November
High       Low

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 453 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.