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Search results; Over 1,000 homes in Castellina in Chianti

Luxe
This Castellina in Chianti villa gives you an infinity pool over vineyards on 4 acres
10 bedrooms, 10 beds, 11.5 private baths
Oct 31 – Nov 7
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4.8 out of 5 average rating, 5 reviews
Top guest favorite
Look out over Chianti rooftops from this penthouse in a 1434 palazzo
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 19 – 24
Top guest favorite
This renovated stone barn gives you Val d’Elsa views and a pool in Castellina
5.0 out of 5 average rating, 97 reviews, 1 bedroom, 3 beds, 1 bath
Oct 29 – Nov 3
Top guest favorite
Sip wine on your private terrace overlooking the hills at this Castellina apartment
4.94 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 25 – 30
Top guest favorite
Tuscan antiques and a fireplace greet you at this Poggibonsi villa apartment
5.0 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bath
Aug 13 – 18
Top guest favorite
This Castellina in Chianti farmstay puts you in an ancient monastery with an infinity pool
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 24 – 29
Top guest favorite
Sip Chianti on your pergola terrace overlooking the vineyards at this Castellina barn
4.97 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 25 – 30
Top guest favorite
This Poggibonsi apartment gives you a private garden, balcony, and barbecue
4.98 out of 5 average rating, 45 reviews, 2 bedrooms, 3 beds, 2 baths
Oct 10 – 15
Top guest favorite
This Castelnuovo Berardenga apartment puts you on a Chianti Classico winery
4.97 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 2.5 baths
Oct 29 – Nov 3
Top guest favorite
Soak in vineyard views from the hot tub at this stone farmhouse in Poggibonsi
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 28 – Sep 2
This Chianti hills home gives you panoramic views, a pool, and alfresco dining
New place to stay, 4 bedrooms, 3 beds, 4 baths
Aug 16 – 21
Top guest favorite
This ground-floor Radda in Chianti flat gives you a fireplace and a piano
4.92 out of 5 average rating, 123 reviews, 1 bedroom, 1 bed, 1 bath
Aug 19 – 24
Guest favorite
A renovated stone barn in Monteriggioni where you’re surrounded by greenery
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bath
Sep 1 – 6
Top guest favorite
This newly renovated Panzano apartment gives you a private courtyard and garden
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Top guest favorite
This two-level Greve in Chianti apartment puts you in the historic center
4.94 out of 5 average rating, 52 reviews, 2 bedrooms, 2 beds, 2.5 baths
Aug 15 – 20
Superhost
Look out over the vineyards from your wooden terrace at this Castellina in Chianti house
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bath
Oct 8 – 13
Top guest favorite
Wake among Chianti vineyards at this Castellina in Chianti condo with a private pergola
4.95 out of 5 average rating, 41 reviews, 1 bedroom, 1 bed, 1 bath
Aug 19 – 24
Top guest favorite
Private room
This eco-lodge in Greve in Chianti puts you among woods and vineyards
4.93 out of 5 average rating, 221 reviews, 1 bedroom, 1 bed, 1 bath
Aug 14 – 19
Top guest favorite
This San Gusmè apartment puts you in a quiet medieval village amid Chianti
4.99 out of 5 average rating, 466 reviews, 2 bedrooms, 3 beds, 2 baths
Oct 26 – 31