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Vacation rentals in Castellina in Chianti

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Castellina in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 103 reviews

Villa di Geggiano - Guesthouse

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Nov 4 – 11

R12,656 ZAR per night
Guest favorite

Cottage in Monteriggioni

4.96 out of 5 average rating, 170 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Dec 10 – 17

R2,783 ZAR per night
Guest favorite

Guesthouse in Greve in Chianti

4.97 out of 5 average rating, 353 reviews

Selvabella in Chianti B&B Il Riccio

Selvabella is a farmhouse situated in the heart of Tuscany, half way between Greve and Panzano in Chianti. Just 35 km from Florence and Siena it is a perfect place to enjoy the beauty of Chianti. Il Riccio is an apartment of 45 square meters. It has a double bedroom, a living-room/bedroom with two sofas/ single beds, a large bathroom and a kitchenette (fridge, sink, microwave and hotplate). It is the perfect place for lovers of nature, cooking and pottery.

Jul 16 – 23

R2,807 ZAR per night

Popular amenities for Castellina in Chianti vacation rentals

Stay near Castellina in Chianti's top sights

Gelateria di Castellina10 locals recommend
Osteria Rosticceria Il Re Gallo6 locals recommend
Antica Trattoria la Torre20 locals recommend
Taverna Squarcialupi4 locals recommend
Il Fondaccio Dai Dottori9 locals recommend
Pizzeria il Fondaccio4 locals recommend

Other great vacation rentals in Castellina in Chianti

Guest favorite

Tower in Fiesole

4.95 out of 5 average rating, 151 reviews

A Big Dream in a Little Tower.

Sep 14 – 21

R16,961 ZAR per night
Guest favorite

Condo in Noce

5.0 out of 5 average rating, 117 reviews

Vergianoni estate nestled in the Chianti with a pool

Jan 30 – Feb 6

R2,304 ZAR per night
Guest favorite

Apartment in Castellina in Chianti

5.0 out of 5 average rating, 42 reviews

Apartment "Gardenia"

Feb 17 – 24

R1,962 ZAR per night
Guest favorite

Home in Castellina in Chianti

4.9 out of 5 average rating, 61 reviews

Casanuova Pietrafitta farm stay

Nov 27 – Dec 4

R2,470 ZAR per night
Guest favorite

Condo in Castellina in Chianti

4.97 out of 5 average rating, 32 reviews

Apartment with terrace and stunning view

Nov 13 – 20

R1,849 ZAR per night
Guest favorite

Home in Castellina in Chianti

5.0 out of 5 average rating, 40 reviews

CHIANTI CLASSICO, VIEWS, WALK TO RESTAURANT

Mar 18 – 25

R3,295 ZAR per night
Guest favorite

Home in Castellina in Chianti

4.97 out of 5 average rating, 76 reviews

Explore Chianti from a Charming Stone House

Oct 30 – Nov 6

R6,175 ZAR per night
Guest favorite

Home in Castellina in Chianti

4.97 out of 5 average rating, 78 reviews

StageROOM03 -Chianti Idillic Country living

Oct 20 – 27

R11,344 ZAR per night
Guest favorite

Barn in Castellina in Chianti

5.0 out of 5 average rating, 39 reviews

Cipressini 1 - Swimming pool and stunning view

Oct 3 – 10

R4,855 ZAR per night
Superhost

Condo in Castellina in Chianti

4.89 out of 5 average rating, 64 reviews

Apartment in the Chianti Classico

Aug 24 – 31

R3,993 ZAR per night
Guest favorite

Apartment in Greve in Chianti

4.9 out of 5 average rating, 63 reviews

Stunning Tuscan apartment for 2

Dec 3 – 10

R2,919 ZAR per night
Guest favorite

Cottage in Castellina in Chianti

4.9 out of 5 average rating, 10 reviews

Chianti cottage with pool

Dec 7 – 14

R5,848 ZAR per night

Quick stats about vacation rentals in Castellina in Chianti

Total rentals

50 properties

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

680 reviews

Nightly prices starting at

R757 ZAR before taxes and fees

Frequently Asked Questions

  • How much does it cost to stay in villa rentals in Castellina in Chianti?

    Experience the best of Castellina in Chianti with our villa rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Castellina in Chianti?

    Yes! Work meets play with ease at over 10 vacation rentals in Castellina in Chianti featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Castellina in Chianti have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly apartment rentals in Castellina in Chianti?

    Four-legged friends are welcome in Castellina in Chianti. Choose from more than 10 apartment rentals for guests traveling with pets.

  • Do villa rentals in Castellina in Chianti have wifi?

    Absolutely! We offer over 10 villa rentals with wifi in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Are there Castellina in Chianti villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 villa rentals with pools in Castellina in Chianti, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly apartment rentals in Castellina in Chianti?

    Castellina in Chianti has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Castellina in Chianti?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Castellina in Chianti