Vacation rentals in Castellina in Chianti

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Top-rated vacation rentals in Castellina in Chianti

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Guest favorite

Home in Panzano In Chianti

4.98 out of 5 average rating, 352 reviews

Old farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Mar 14 – 21

G$22,852 GYD per night

Guest favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 164 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Nov 4 – 11

G$106,135 GYD per night

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 106 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.

Mar 23 – 30

G$103,323 GYD per night

Guest favorite

Cottage in Monteriggioni

4.97 out of 5 average rating, 173 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 14 – 21

G$30,280 GYD per night

Superhost

Apartment in Castellina in Chianti

4.81 out of 5 average rating, 253 reviews

Relax Chianti. Apartment with pool and garden

Apartment nestled in the Chianti Classico hills, in the Borgo di Tregole, 5 km from Castellina in Chianti. Casa Cinzia is a private apartment inside a typical Tuscan farmhouse. Suitable for those who want to spend a vacation immersed in nature full of relaxation and silence. Ideal starting point for visiting the most important places in Tuscany. The apartment is equipped with all comforts. Linen is included in the price. Children are welcome

Mar 15 – 22

G$22,901 GYD per night

Guest favorite

Guest suite in Greve in Chianti

4.94 out of 5 average rating, 379 reviews

Selvabella in Chianti B&B. Suite Lo Scricciolo

Lo Scricciolo is located in the tower, the highest building of the house. By a separate entrance from the main house, through a loggia overlooking the Tuscan countryside, you access the first floor. Here are the living room with wooden ceiling and a small bathroom. From the living room, an old stone staircase leads to the upper floor where there is a large double bedroom. Lo Scricciolo has an efficient system of heating for the cold season.

Oct 21 – 28

G$25,445 GYD per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 307 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Nov 30 – Dec 7

G$33,079 GYD per night

Guest favorite

Apartment in Greve in Chianti

4.99 out of 5 average rating, 112 reviews

The Nest in the Chianti

We would like to inform you that for this emergency we are doing everything we can to help and protect our guests by adopting a detailed and strict cleaning, disinfecting and sanitizing all parts of the house. Cozy apartment, finely renovated in the heart of the historic center on the second floor overlooking the beautiful Piazza di Greve in Chianti. On its condominium terrace you can spend beautiful moments of relaxation.

Jan 20 – 27

G$21,662 GYD per night

Superhost

Farm stay in Greve in Chianti

4.82 out of 5 average rating, 205 reviews

Simplicity in Organic Farmhouse Azzurro

L'agriturismo produce frutta olio e ortaggi con il metodo biologico , situato lungo la valle del fiume Greve, circondato da boschi ma vicinissimo al paese, nel centro del Chianti ad meno di un ora da Firenze e Siena . Ideale per visitare tutte le città d'arte della Toscana , ma anche per passeggiate nei boschi e per una vacanza di relax circondati solo dalla pace e dalla tranquillità

Aug 28 – Sep 4

G$17,303 GYD per night

Guest favorite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 199 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Jan 4 – 11

G$29,843 GYD per night

Guest favorite

Apartment in Castellina in Chianti

4.92 out of 5 average rating, 167 reviews

Casa Tatini your house in Chianti

Casa Tatini is situated in San Martino near Castellina in Chianti in the territory of the Chianti Gallo Nero. We make of our Guests an apartment composed by a bedroom with a kink size bed, by a kitchen-living room and by a bathroom with shower.

Dec 12 – 19

G$19,084 GYD per night

Guest favorite

Farm stay in Greve in Chianti

4.86 out of 5 average rating, 178 reviews

La Capanna delle Bartaline

L'appartamento si trova all'interno della nostra azienda agricola ad 1 Km. da Panzano. E' di nuova ristrutturazione e ben curato nei dettagli, confortevole e luminoso, adatto per ogni tipo di soggiorno. Vista mozzafiato sulle colline toscane.

Sep 7 – 14

G$27,454 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Castellina in Chianti vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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, 153 reviews

A Big Dream in a Little Tower.

Sep 16 – 23

G$182,368 GYD per night

Guest favorite

Home in Castellina in Chianti

4.91 out of 5 average rating, 64 reviews

Casanuova Pietrafitta farm stay

Feb 5 – 12

G$29,419 GYD per night

Guest favorite

Apartment in Castellina in Chianti

4.98 out of 5 average rating, 42 reviews

CORBEZZOLO

Oct 13 – 20

G$32,650 GYD per night

Superhost

Condo in Castellina in Chianti

4.89 out of 5 average rating, 64 reviews

Apartment Rosemary/Lavander in Chianti Classico

Mar 26 – Apr 2

G$39,293 GYD per night

Guest favorite

Home in Castellina in Chianti

5.0 out of 5 average rating, 40 reviews

CHIANTI CLASSICO, VIEWS, WALK TO RESTAURANT

Aug 26 – Sep 2

G$35,848 GYD per night

Guest favorite

Condo in Castellina in Chianti

4.97 out of 5 average rating, 33 reviews

Apartment with terrace and stunning view

Nov 10 – 17

G$20,114 GYD 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 27 – Nov 3

G$67,176 GYD per night

Guest favorite

Home in Castellina in Chianti

4.97 out of 5 average rating, 78 reviews

StageROOM03 -Chianti Idillic Country living

Sep 5 – 12

G$128,346 GYD per night

Show all

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
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
670 reviews
Nightly prices starting at
G$8,360 GYD 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 $120 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 10 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 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Castellina in Chianti

Top-rated vacation rentals in Castellina in Chianti

Vacation rentals for every style

Apartments

Hotels

Unique stays

Popular amenities for Castellina in Chianti vacation rentals

Stay near Castellina in Chianti's top sights

Other great vacation rentals in Castellina in Chianti

Tower in Fiesole

Home in Castellina in Chianti

Apartment in Castellina in Chianti

Condo in Castellina in Chianti

Home in Castellina in Chianti

Condo in Castellina in Chianti

Home in Castellina in Chianti

Home in Castellina in Chianti

Quick stats about vacation rentals in Castellina in Chianti

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

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

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

Do apartment rentals in Castellina in Chianti have air conditioning?

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

Do villa rentals in Castellina in Chianti have wifi?

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

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

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

Destinations to explore