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Holiday rentals in Castellina in Chianti

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Top-rated holiday rentals in Castellina in Chianti

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

Guest favourite

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.

4–11 Nov

€ 626 per night
Guest favourite

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.

10–17 Dec

€ 136 per night
Guest favourite

Guest house 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.

16–23 Jul

€ 137 per night

Popular amenities for Castellina in Chianti holiday 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 holiday rentals in Castellina in Chianti

Guest favourite

Tower in Fiesole

4.95 out of 5 average rating, 151 reviews

A Big Dream in a Little Tower.

14–21 Sep

€ 830 per night
Guest favourite

Apartment in Noce

5.0 out of 5 average rating, 117 reviews

Vergianoni estate nestled in the Chianti with a pool

30 Jan – 6 Feb

€ 120 per night
Guest favourite

Flat in Castellina in Chianti

5.0 out of 5 average rating, 42 reviews

Apartment "Gardenia"

17–24 Feb

€ 96 per night
Guest favourite

Home in Castellina in Chianti

4.9 out of 5 average rating, 61 reviews

Casanuova Pietrafitta farm stay

27 Nov – 4 Dec

€ 126 per night
Guest favourite

Apartment in Castellina in Chianti

4.97 out of 5 average rating, 32 reviews

Apartment with terrace and stunning view

13–20 Nov

€ 91 per night
Guest favourite

Home in Castellina in Chianti

5.0 out of 5 average rating, 40 reviews

CHIANTI CLASSICO, VIEWS, WALK TO RESTAURANT

18–25 Mar

€ 168 per night
Guest favourite

Home in Castellina in Chianti

4.97 out of 5 average rating, 76 reviews

Explore Chianti from a Charming Stone House

30 Oct – 6 Nov

€ 302 per night
Guest favourite

Home in Castellina in Chianti

4.97 out of 5 average rating, 78 reviews

StageROOM03 -Chianti Idillic Country living

20–27 Oct

€ 554 per night
Guest favourite

Barn in Castellina in Chianti

5.0 out of 5 average rating, 39 reviews

Cipressini 1 - Swimming pool and stunning view

3–10 Oct

€ 237 per night
Superhost

Apartment in Castellina in Chianti

4.89 out of 5 average rating, 64 reviews

Apartment in the Chianti Classico

24–31 Aug

€ 201 per night
Guest favourite

Flat in Greve in Chianti

4.9 out of 5 average rating, 63 reviews

Stunning Tuscan apartment for 2

3–10 Dec

€ 143 per night
Guest favourite

Cottage in Castellina in Chianti

4.9 out of 5 average rating, 10 reviews

Chianti cottage with pool

7–14 Dec

€ 286 per night

Quick stats about holiday 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

€ 37 before taxes and fees

Destinations to explore

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