Home Vacation Rentals By Owner In Castellina In Chianti, TOS

Showing 60 Of 97 Vacation Rentals
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Exceptional(2)

$183.85

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Villa

Ceccatelli In Castellina in Chianti, Tuscany

Castellina In Chianti, Si, Italy

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***brProperty for exclusive usebrStone-built farmhouse (150 m2) situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.). At guests’ disposal a private fenced-in swimming pool (6x16)(01/05-13/10). The clients can make use of a laundry room (washing machine, dryer) which is situated near to property BETTINI and shared with the guests of the other units in the property. Simple style but complete furniture with some period pieces. Baby bed available to be requested when booking). Possibility to rent pool towels upon payment (3 euros/towel). It is possible to purchase the estate produce. Possibility of guided tasting tours of the medieval cellar with wine and olive oil produced on the estate. Parking. Access along 300 m of dirt track road.brPLEASE NOTE: Pets admitted on payment (Euro 30/animal/per week). brArrivals must be between 3.00pm and 7.00pm.br1 baby bed included in the rates. For the second baby bed, a supplement of 35 Euro/week is requested.ACCOMMODATION: 1st fl. (access from external staircase with small covered terrace): living room with fireplace (satellite TV), kitchen/dining room (dishwasher, small electric oven), 2 double bedrooms one of which has a bathroom with shower, 1 twin bedded room, 1 single bedroom, 2 bathrooms with shower. On the gr. fl. there are some rooms which currently cannot be used. LOCATION: 7 km Castellina in Chianti (grocery shops, tennis), 10 km Monteriggioni (fascinating walled town), 16 km Poggibonsi (any kind of shops), 23 km Siena, 26 km San Gimignano, 55 km Florence. brbr Final cleaning per booking. In cash 250.00 Eurobr Refundable deposit (to be handed over on arrival) per booking. In cash 350.00 Eurobr Tourist tax per person/day 2.00 Euro
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Sleep 7

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Exceptional(1)

$1229.93

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Villa

Podere Gabbiano, Castellina in Chianti, Siena and Chianti

Castellina In Chianti, Siena and Chianti, Italy

Podere Gabbiano is situated in a stunning private countryside setting, offering 360-degree views of vineyards, olive groves and oak forests. Guests will be captivated by the sunsets that bathe the rolling hills in golden light. This is a property where history, comfort and natural beauty come together to create a peaceful and elegant retreat.brbrbrbrLocated in a hillside opening between the charming hilltop towns of Castellina in Chianti and Panzano in Chianti, the villa is perfectly placed for guests who want to enjoy the region’s renowned food, wine and artisan culture. Both towns offer a range of shops and restaurants. Each has its own COOP supermarket. Panzano is home to the famous butcher Dario Cecchini, known throughout Italy and beyond, with a traditional butcher’s shop and his celebrated restaurant Officina della Bistecca. In Castellina, the Gelateria di Castellina is not to be missed. It is known for some of the best ice cream in the area. Siena, San Gimignano, Arezzo and Florence are all ideal destinations for day trips.brbrOriginally built as a working farmhouse, the villa has been carefully restored and transformed into an elegant holiday home. Guests can dine al fresco under the open stone barn, surrounded by views of the countryside. The pool area is another highlight, especially at sunset, and the original stone oven is perfect for memorable pizza evenings.brbrbrbrInside, Podere Gabbiano blends traditional features with modern comfort. Terracotta floors, archways and ceilings have been carefully preserved. Large bedrooms and well-appointed bathrooms provide space and privacy for all guests.brbrbrbrPodere Gabbiano is a timeless Tuscan retreat offering style, comfort and unforgettable views.brbrGround FloorbrbrbrbrEntrance HallbrbrSideboard, bench, door to terrace, terrace with outside furniture, sofa, chairs, table, stairs to 1st-floor (no handrail).brbrbrbrLounge (steps down no handrail)brbrSofas, footstools, coffee tables, sideboards, fireplace (decoration only), door to garden.brbrbrbrWine Tasting RoombrbrTable, chairs, fridge, sideboard, door to garden.brbrbrbrKitchenbrbrFully equipped, induction hob, island unit, large fridge/ freezer, table, chairs, door to terrace, terrace with table and chairs.brbrbrbrGym/ Games RoombrbrEquipped with weights, table football.brbrbrbrUtility RoombrbrWashing machine, dryer.brbrbrbrFirst FloorbrbrbrbrBedroom 1brbrTwin beds (can be converted into double beds), bedside tables, chest of drawers, wardrobe, desk, air-conditioning.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrLoungebrbrSofas, armchairs, coffee tables, fireplace (decoration only),brbrTV, door to balcony with stairs to the terrace.brbrbrbrBedroom 2brbrDouble bed (can’t be converted in twin beds), bedside tables, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC, built-in wardrobe.brbrbrbrBedroom 3brbrDouble bed (can’t be converted into twin beds), bedside table, chair, wardrobe, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrBedroom 4brbrDouble bed (can’t be converted into twin beds), bedside tables, wardrobe, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrSuitebrbrLoungebrbrSofa, desk, wardrobe, table, chairs.brbrbrbrBedroom 5brbrDouble bed (can’t be converted into twin beds), bedside tables, chest of drawers, built-in shelving, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 11 metresbrbrWidth: 7 metresbrbrDepth: 0.8 - 1.8 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: SunloungersbrbrCleansed: ChlorinebrbrDistance from villa: 30 metres
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Sleep 10

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$133.81

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Apartment

La Foresta by Interhome

Castellina In Chianti, Castellina in Chianti, Italy

Castellina in Chianti: Agriturismo La Foresta, surrounded by fields and vineyards. 4 apartments in the residence. 10 km from the centre of Castellina in Chianti, 12 m from the centre of Siena, in a quiet, sunny position, in the countryside. For shared use: property, plants and trees, meadow, swimming pool fenced (6 x 14 m, seasonal availability: 15.May. - 15.Oct.). Outdoor shower, patio, terrace, garden furniture, barbecue, pool maintenance by the owner/gardener. In the house: reception, washing machine (for shared use). 2 km long bumpy motor access to the house. Roofed, parking at the house. Shop 6 km, grocery 6 km, supermarket 6 km, restaurant 2 km, bus stop Via Chiantigiana 2 km, railway station Siens 12 km. Nearby attractions: Siena 12 km, Greve in Chianti 20 km, SAn Gimignano 25 km, Firenze 65 km. Please note: car recommended. Baby equipment (included). Local sale of farm products. All houses/apartments are individually designed/furnished.brLe Macine, 2-room apartment 30 m2 on 2 levels. Practical and rustic furnishings: small living/sleeping room with dining table, kitchen corner and TV (flat screen). Open kitchen (oven, 4 induction hot plates, kettle, electric coffee machine). Shower/WC. Upper floor: (steep stair) open gallery with 1 double bed. Gas heating (extra). Patio. Terrace furniture, barbecue. Very beautiful panoramic view. Facilities: children's high chair, baby cot for up to 2 year olds. Internet (WiFi, free). Parking (roofed) at the house. Please note: non-smokers only. Maximum 1 pet/ dog allowed. Private entrance, fire extinguisher. IT052005B57VSC3FJ8brbrIncluded in price:brERV cancellation insurancebrPower costsbrFinal cleaning (Basic cleaning is always carried out by the guest)brLaundry (initial supply of bed linen and towels)brRoofed parkingbrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / Highchairbrbr #IT5252.625.2
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$245.52

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Apartment

La Foresta by Interhome

Castellina In Chianti, Castellina in Chianti, Italy

Castellina in Chianti: Agriturismo La Foresta, surrounded by fields and vineyards. 4 apartments in the residence. 10 km from the centre of Castellina in Chianti, 12 m from the centre of Siena, in a quiet, sunny position, in the countryside. For shared use: property, plants and trees, meadow, swimming pool fenced (6 x 14 m, seasonal availability: 15.May. - 15.Oct.). Outdoor shower, patio, terrace, garden furniture, barbecue, pool maintenance by the owner/gardener. In the house: reception, washing machine (for shared use). 2 km long bumpy motor access to the house. Roofed, parking at the house. Shop 6 km, grocery 6 km, supermarket 6 km, restaurant 2 km, bus stop Via Chiantigiana 2 km, railway station Siens 12 km. Nearby attractions: Siena 12 km, Greve in Chianti 20 km, SAn Gimignano 25 km, Firenze 65 km. Please note: car recommended. Baby equipment (included). Local sale of farm products. All houses/apartments are individually designed/furnished.brForesta 2, 4-room apartment 100 m2, on the upper floor. Spacious, rustic and antique furnishings: large living/sleeping room with open-hearth fireplace and TV (flat screen). 2 double bedrooms, each room with air conditioning. 1 room with 2 beds (80 cm), air conditioning. Kitchen (oven, dishwasher, Gas stove, 4 gas rings, kettle, electric coffee machine) with dining table. 2 showers/bidet/WC. Gas heating (extra), air-conditioning. Balcony, patio. Terrace furniture, barbecue. Very beautiful panoramic view of the countryside. Facilities: washing machine, children's high chair, baby cot for up to 2 year olds, hair dryer, logs (extra). Internet (WiFi, free). Parking (roofed) at the house. Please note: non-smokers only. Maximum 1 pet/ dog allowed. Private entrance, fire extinguisher. IT052005B57VSC3FJ8brbrIncluded in price:brAir-conditioningbrERV cancellation insurancebrPower costsbrFinal cleaning (Basic cleaning is always carried out by the guest)brLaundry (initial supply of bed linen and towels)brRoofed parkingbrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / Highchairbrbr #IT5252.625.3
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Sleep 6

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Exceptional(1)

$570.17

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Villa

Poggio Tondo, Castellina in Chianti, Siena and Chianti

Castellina In Chianti, Siena and Chianti, Italy

Poggio Tondo is a spacious country house in complete seclusion, set on a hill in the heart of the Chianti Classico. Surrounded by cypress trees and forest, it offers sweeping panoramic views of olive groves, vineyards, the rolling hills of Chianti and, in the distance, the skyline of Siena. With a well-kept garden, large terrace, and a beautiful pool, it is the perfect setting for a relaxing holiday with family or friends.brbrbrbrThe location is peaceful and rural, yet very well connected. The wineries Castello di Fonterutoli and Tregole can both be reached on foot. Castellina in Chianti is only four kilometres away and offers restaurants, cafés, a supermarket, and the popular Gelateria di Castellina, known for its delicious ice cream. Siena is less than half an hour away by car. San Gimignano, Florence, and Arezzo also make great destinations for day trips.brbrThe two-storey stone house with brown wooden shutters and a full-length balcony on the upper floor has the character of an alpine retreat but fits naturally into the Tuscan setting. The large terrace at the front opens out onto the garden and pool area, perfect for enjoying the outdoors.brbrbrbrInside, Poggio Tondo features a bright, welcoming atmosphere with tiled floors and comfortable, spacious interiors. Both floors include living and dining areas as well as kitchens. The upstairs living room opens onto the balcony, an ideal spot for morning coffee or a quiet evening with a view.brbrbrbrPoggio Tondo offers space, privacy, and nature in perfect harmony.brbrGround FloorbrbrbrbrLounge/ DinerbrbrSofas, coffee table, TV, fireplace, side tables, long dining table, chairs, chest of drawers, mosquito screen.brbrbrbrKitchenbrbrFully equipped, gas hob with 5 rings, diswasher, fridge/ freezer, chairs, mosquito screen.brbrbrbrBathroombrbrShower, sink, bidet, WC, mosquito screen.brbrbrbrFirst FloorbrbrbrbrLounge/ DinerbrbrSofas, coffee tables, TV, table chairs, Welsh dresser, French doors to a large balcony, balcony with table and chairs, mosquito screen.brbrbrbrKitchenbrbrFully equipped, gas hob with 5 rings, diswasher, fridge/ freezer, chairs, washing machine, mosquito screen.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), wardrobe, chair, baby cot, ceiling fan, mosquito screen.brbrbrbrBathroombrbrShower, sink, bidet, WC, mosquito screen.brbrbrbrBedroom 2brbrDouble bed (cannot be converted into twin beds), bedside tables, wardrobe, chest of drawers, ceiling fan, mosquito screen, French door to balcony.brbrbrbrBedroom 3brbrOne single and one French-size bed (can’t be converted into a double), bedside table, wardrobe, ceiling fan, mosquito screen.brbrbrbrBathroombrbrShower, sink, bidet, WC, mosquito screen.brbrbrbrPrivate PoolbrbrLength: 12 mbrbrWidth: 4 mbrbrDepth: from 1,20 m to 1,60 mbrbrEntrance: Roman stepsbrbrOpening times: always openbrbrFenced: nobrbrFurnished: parasol, deckchairs, sundoungersbrbrCleansed: chlorinebrbrDistance from the villa: 26 m
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Sleep 6

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$1143.82

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Villa

Setriolo by Arceno Rentals Club, exclusive Villa and Annex, Pool A/C Concierge

Castellina In Chianti, Siena, Italy

SETRIOLO IS NEWLY ADVERTISED. FOR THE FIRST THREE RESERVATIONS RECEIVED A WINE TASTING WILL BE OFFERED COMPLIMENTARY BY JUAN; THE OWNER OF THE VINEYARDS OF SETRIOLObrbrSetriolo is a very beautiful and recently renovated ‘Podere’, a running winemaking farm about five kilometres from Castellina in Chianti with spectacular views over the vines, olive groves and lines of cypress trees.brSetriolo consists of a main building and an annex, a private pool, gardens and an outdoor kitchen terrace. Refurbished with elegance and high standards, it features air conditioning and satellite WiFi. The premises can accommodate ten guests, perfect for families and groups of friends.brThe apartment in the main building is on the upper floor, recently restored into a modern and tastefully decorated property, blending with the retained original features of the building. It counts a very comfortable living space, a perfectly appointed kitchen, three the bedrooms with three bathrooms and two outdoor terraces. brOpposite the main building across the courtyard is the annex, refurbished with a living area, kitchenette, two bedrooms and one bathroom.brAround both buildings the gardens have been tastefully and sensitively maintained. brFrom the sun deck and the exclusive swimming pool the view is just gorgeous. The area is very tranquil and one can imagine just soaking it all up with an aperitivo in the evening from one of many outdoor areas. brAside the annex is the barbecue outdoor area which consists of seating, low tables and an outdoor kitchen with stainless steel worktop, induction hob and sink. There is a mobile barbecue and a gas-powered pizza oven. Adjacent to this is a pergola, beneath which is a dining table and seating for ten. brSetriolo is a working farm and the lower floor of the main building has been retained for the wine making. Juan, the owner of the Podere, is sensitive to the hours of privacy that guests would wish for; however, he may be present to deal with the activities necessary for the operation of the Podere. He is welcoming for guests to enjoy a wine and oil tasting should they wish to. In September guests may well enjoy the possibility of helping with the vine harvesting, as well as with the olive harvest in October.
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Bath 4

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$326.97

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Private Vacation Home

Olimpia by Interhome

Castellina In Chianti, Castellina in Chianti, Italy

Pretty stone farmhouse. The property, made up of two connected units, is immersed in the countryside in the heart of Chianti, an ideal area for visiting Tuscany. Country house Olimpia, 400 m a.s.l., renovated in 2023. 2 km from the centre of Castellina in Chianti, 19 km from the centre of Monteriggioni, 50 km from the centre of Firenze, in a sunny position on a slope, in the countryside. For shared use: garden 1'000 m2 (not fenced), swimming pool fenced (14 x 6 m, depth 120 - 220 cm, seasonal availability: 01.May. - 30.Sep.). Outdoor shower, garden furniture. Private: garden furniture, barbecue. In the house: central heating system, heating to be paid on the spot, heating available only from 01.Nov. - 04.Apr.. Motor access to the house (200 m via unmade road). Parking on the premises. Shop 2 km, supermarket 2 km, restaurant 2 km, bus stop 500 m, sandy beach Castiglione della Pescaia 120 km, thermal baths Rapolano Terme 56 km. Nearby attractions: Radda in Chianti 8 km, Volpaia 15 km, Greve in Chianti 18 km, Gaiole in Chianti 19 km, San Gimignano, Siena 30 km. The fenced pool is shared with another 5-seater house.br4-room house 120 m2 on 2 levels, on the ground floor. Renovated in 2023, comfortable and cosy furnishings: living/dining room with open-hearth fireplace, satellite TV and air conditioning. Exit to the garden. Open gallery with 1 double bed and air conditioning. Kitchenette (4 hot plates, oven, dishwasher, freezer). Shower/bidet/WC. Upper floor: living/dining room with 1 double sofabed, open-hearth fireplace and satellite TV. 1 double bedroom with air conditioning. Exit to the garden. Kitchenette (4 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer). Terrace furniture, barbecue. Panoramic view of the countryside. Facilities: washing machine, iron, children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). IT052005C2P4EUFYD7brbrIncluded in price:brERV cancellation insurancebrFinal cleaning (Basic cleaning is always carried out by the guest)brLaundry (initial supply of bed linen and towels)brWeekly laundry (bed linen and towels)brInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / HighchairbrPool towelsbrbrDeposit information: brBreakage deposit in cash: 300.0 EURbr #IT5252.980.1
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Sleep 6

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$143.12

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Apartment

La Foresta by Interhome

Castellina In Chianti, Castellina in Chianti, Italy

Castellina in Chianti: Agriturismo La Foresta, surrounded by fields and vineyards. 4 apartments in the residence. 10 km from the centre of Castellina in Chianti, 12 m from the centre of Siena, in a quiet, sunny position, in the countryside. For shared use: property, plants and trees, meadow, swimming pool fenced (6 x 14 m, seasonal availability: 15.May. - 15.Oct.). Outdoor shower, patio, terrace, garden furniture, barbecue, pool maintenance by the owner/gardener. In the house: reception, washing machine (for shared use). 2 km long bumpy motor access to the house. Roofed, parking at the house. Shop 6 km, grocery 6 km, supermarket 6 km, restaurant 2 km, bus stop Via Chiantigiana 2 km, railway station Siens 12 km. Nearby attractions: Siena 12 km, Greve in Chianti 20 km, SAn Gimignano 25 km, Firenze 65 km. Please note: car recommended. Baby equipment (included). Local sale of farm products. All houses/apartments are individually designed/furnished.brForesta 1, 2-room apartment 55 m2, on the ground floor. Practical and rustic furnishings: living/dining room with dining table and TV (flat screen). 1 double bedroom. Open kitchen (oven, Gas stove, 4 gas rings, kettle, electric coffee machine). Shower/WC. Heating (extra). Patio. Terrace furniture, barbecue. Very beautiful panoramic view of the countryside. Facilities: children's high chair, baby cot for up to 2 year olds. Internet (WiFi, free). Parking (roofed) at the house. Please note: non-smokers only. Maximum 1 pet/ dog allowed. Private entrance, fire extinguisher. IT052005B57VSC3FJ8brbrIncluded in price:brERV cancellation insurancebrPower costsbrFinal cleaning (Basic cleaning is always carried out by the guest)brLaundry (initial supply of bed linen and towels)brRoofed parkingbrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / Highchairbrbr #IT5252.625.1
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$167.56

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Apartment

La Foresta by Interhome

Castellina In Chianti, Castellina in Chianti, Italy

Castellina in Chianti: Agriturismo La Foresta, surrounded by fields and vineyards. 4 apartments in the residence. 10 km from the centre of Castellina in Chianti, 12 m from the centre of Siena, in a quiet, sunny position, in the countryside. For shared use: property, plants and trees, meadow, swimming pool fenced (6 x 14 m, seasonal availability: 15.May. - 15.Oct.). Outdoor shower, patio, terrace, garden furniture, barbecue, pool maintenance by the owner/gardener. In the house: reception, washing machine (for shared use). 2 km long bumpy motor access to the house. Roofed, parking at the house. Shop 6 km, grocery 6 km, supermarket 6 km, restaurant 2 km, bus stop Via Chiantigiana 2 km, railway station Siens 12 km. Nearby attractions: Siena 12 km, Greve in Chianti 20 km, SAn Gimignano 25 km, Firenze 65 km. Please note: car recommended. Baby equipment (included). Local sale of farm products. All houses/apartments are individually designed/furnished.brForesta 4, 3-room apartment 60 m2, on the ground floor. Practical and rustic furnishings: living/dining room with TV (flat screen). Exit to the garden, to the terrace. 1 double bedroom with fan. Exit to the terrace. 1 room with 2 beds (80 cm), fan. Open kitchen (oven, dishwasher, 4 gas rings, kettle, electric coffee machine) with dining table. Shower/bidet/WC. Gas heating (extra). Terrace, large patio. Terrace furniture, barbecue. Very beautiful panoramic view of the countryside. Facilities: children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). Parking (roofed) at the house. Please note: non-smokers only. Maximum 1 pet/ dog allowed. Private entrance, fire extinguisher. IT052005B57VSC3FJ8brbrIncluded in price:brERV cancellation insurancebrPower costsbrFinal cleaning (Basic cleaning is always carried out by the guest)brLaundry (initial supply of bed linen and towels)brRoofed parkingbrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / Highchairbrbr #IT5252.625.4
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$1117.06

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Villa

Chianti Escape, Pool&Vines Tenuta Bibbiano-I Sodi

Castellina In Chianti, Castellina in Chianti, Italy

Luxury villa nestled in the heart of Chianti, ideal for groups of up to 16 guests looking for privacy, comfort and an authentic experience between nature and wine. br The property offers 9 bedrooms, large and bright rooms, a large convivial living room and a fully equipped kitchen, perfect both for independent stays and for private services on request. br Outside, the villa is surrounded by vineyards and has a private panoramic pool, garden and terrace equipped for outdoor lunches and dinners: spaces designed for relaxing in total tranquility. br A private SPA with sauna and Turkish bath is also available, accessible by reservation and with a supplement, ideal for adding an exclusive moment of well-being to the stay. br The real added value is the experience on the estate: the possibility of tastings of wine and oil produced on site and tours through the vineyards, to experience Chianti in an authentic and engaging way. brbr br Strategic position, immersed in quiet but convenient for visiting Castellina in Chianti, Siena (25 min) and Florence (45 min). br Perfect for large families, groups of friends and private events, it is a rare solution for those looking for large spaces, privacy and an exclusive context in Tuscany. br Tenuta Bibbiano- I Sodi is a haven of beauty, silence and well-being in the heart of Chianti, an ideal choice for those who want to combine relaxation, nature and quality in a single experience. br br brFeatures: br br br br 9 bedrooms br br br br br 13 beds br br br br br 6 bathrooms br br br br br fully equipped kitchen br br br br br large living areas ideal for groups br br br Panoramic private pool br br br Garden and open spaces br br br BBQ area and outdoor dining area br br br Vineyards and olive groves around the property br br SPA (Sauna, Turkish Bath, Emotional Shower) br The Estate (wine and oil tasting, vineyard tours, experiences related to the territory) br Strategic position (25 min from Siena, about 1 hour from Florence, near iconic villages and Chianti wineries) br The ideal place for groups of friends, large families, retreats (yoga, corporate, wellness) and private events (on request) br br brbrCity Tax: € 2,00 per person per night to pay at check-in starting from 1 nights for a maximum of 7 nightsbrbrbrExtra: AIR CONDITIONING Free of charge, CRIB Free of charge, ELECTRICITY Free of charge, ADDITIONAL BED Free of charge, HEATING Free of charge, LINEN AND TOWELS Free of charge, PRIVATE SWIMMING POOL Free of charge, SAUNA € 150,00 Per day (upon request) from 01/01/2026 until 31/12/2026, WASHING MACHINE Free of chargebrPets - not allowed
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Sleep 16

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$470.1

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Private Vacation Home

Fully renovated Chianti country home, 10 min from Siena; stunning views

Castellina In Chianti, Toscana, Italy

This beautiful 2-bedroom, 2-bathroom Tuscan country home is composed of a ground floor with a comfortable and welcoming living area with a wood fireplace, a dining area laid out around a farmhouse table that doubles as an island for the fully equipped kitchen. The living area opens up to a pergola, ideal for al-fresco dining and garden with stunning views of the surrounding hills and vineyards. The garden houses a BBQ area and a marble carved hot tub. The ground floor also houses a first bedroom and its en-suite bathroom. The first floor houses the master bedroom and its bathroom. A complete renovation and refurbishment of the house was completed in June 2019 to the highest possible quality and modern comfort. brThe property is part of StageROOMS and therefore guarantees luxury amenities and five star standards of hospitality.brbrThis beautiful house is located in the Borgo di Tuopina, an hamlet in the heart of the Chianti, the world famous Italian wine region. The property is just 10 minutes away from Siena and the famous Castello di Monteriggioni and a short drive from other must-see Tuscan towns such as Florence and San Gimignano. The Borgo is located on one of the most beautiful driving routes in Italy, passing acre upon acre of vineyards producing the world-famous Chianti Classico DOCG. The hamlet breaths the typical Tuscany ambiance of idyllic countryside living. Surrounded by olive trees, the property includes a shared swimming pool for guests to enjoy during the summer period ( beginning of June-end of August)
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Exceptional(1)

$1517.32

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Villa

Villa Tregole by MMega

Castellina In Chianti, SI, Italy

External DescriptionbrbrbrbrVilla Tregole is located in the beautiful Chianti countryside, in the village of Fonterutoli, near Castellina in Chianti. Surrounded by a large fenced garden with lawn, flowers and trees, the property boasts a cozy open glass veranda, furnished with a dining table for 16 people and a lounge area with armchairs and sofas, perfect for relaxing while sipping a good glass of wine.brbrAt an upper level of the garden there is a beautiful infinity pool (13 x 7 m, depth from 1 to 2.40 m), open from March to October, and equipped with sun loungers, hydromassage area and external shower. From the pool you can admire a splendid panorama of the surrounding Tuscan landscape.brbrAmong the external facilities you will also find a barbecue, a wood-burning pizza oven, a private parking for 3 cars, and a ping pong table, ideal for the entertainment of adults and children.brbrLastly, at guests' disposal some e-bikes (at an extra cost) and a charging station for electric cars.brbrbrbrInternal DescriptionbrbrbrbrVilla Tregole is made up of the main building and a dependance, and can accommodate up to 16 people in total with 7 bedrooms and 6 bathrooms. The main building is divided into 3 comfortable independent apartments that are not internally connected to each other. Internet Wifi is included. The living area and all bedrooms are equipped with air conditioning. All windows are provided with mosquito nets. 2 baby cots and 2 high chairs are available. Pets are allowed at an extra cost.brbrbrbrMain building: The main building is spread over 2 floors and can sleep up to 14 people. On the ground floor there are 2 fully equipped kitchens, 2 living areas with sofa, fireplace, tv and dining table, and a mezzanine with single bed.brbrThe sleeping area is composed of 2 double bedrooms (both with ensuite bathroom with shower), 1 triple bedroom (with a double bed + a single bed and ensuite bathroom with shower), and 1 single bedroom.brbrOn the upper floor there is another equipped kitchen and a sitting room. Following is 1 double bedroom (with ensuite bathroom with shower), 1 triple bedroom (with a double bed + a single bed and ensuite bathroom with shower), and lastly a mezzanine with study.brbrbrbrDependance: The dependance can accommodate up to 2 people, is set on one single level (on the ground floor), and consists of an equipped kitchen and a double bedroom with ensuite bathroom with shower.brbrbrbrIT052005B4YP63KC2MbrbrIT052005C2E2S94FKXbrbrIT052005B4ZC2UUQVBbrbrbrbrPrices and conditionsbrbrbrbrIncluded in the price: House, garden and pool maintenance; Internet Wifi.brbrbrbrExcluded from the price: Final cleaning (250.00€); utilities (water, gas, electricity - 55.00€ per day); heating during winter months (120.00€ per day); pets (15.00€ per day per pet); dinner/lunch except drinks (55.00€ per person; 23.00€ children from 6 to 12 years; free for children under 6 years); cooking class except drinks (90.00€ per person, adults only, with a minimum of 4 paying guests; more than 10 adults 75.00€ per person; 27.00€ children from 6 to 12 years; free for children under 6 years); continental breakfast (20.00€ per person, all-inclusive; 10.00€ children from 6 to 12 years; free for children under 6 years); pizza night with chef and wood-burning oven (40.00€ per person; 20.00€ children from 6 to 12 years; free for children under 6 years); e-bikes (30.00€ per day per bike); dryer (5.00€ per use). Tourist tax if required (the amount usually varies, depending on location, from 0.50€ to 4.00€ per person per night for a maximum of seven nights, excluding minors, and will be paid upon arrival).brbrbrbrSecurity deposit: Customers are required to pay 800.00€ security deposit upon arrival (cash), which will be returned at the end of the stay upon any damages.
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$322.66

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Private Vacation Home

Chianti Classico Home Panoramic View 6, Castellina in Chianti, Italy

Castellina In Chianti, Castellina in Chianti, Italy

A charming Tuscan home in the heart of Castellina in Chianti. This beautifully restored old townhouse sleeps 6 people and makes an ideal base for exploring the glorious Chianti Classico region and the historic cities of Tuscany.brbrThe front door is just off the main square, and reached through a peaceful, private garden, with magnificent views over the neighbouring countryside. Elegant stairs lead from the entrance hall up to the first-floor living area. With terracotta floors and antique furniture, the apartment retains its original charm. The spacious living room is furnished with a sofa and armchairs, an open fireplace and a Smart TV. The adjacent kitchen/dining area includes a dining table and a well-equipped kitchen. The kitchen includes a cooker hob, oven, microwave, dishwasher, fridge and coffee machine.brbrSleepingbrThere are 3 lovely bedrooms, each tastefully decorated with antique furniture including a double bed, wardrobe and chest of drawers. Each bedroom has an en suite bathroom.brbrBathroomsbrThe 3 en suite bathrooms are all equipped with a shower, basin, bidet and WC.brbrAdditionalbr• Free Wifi • Smart TV • Private, fenced garden • Central heating (available from 15th October to 15th April) & open fireplace (wood not included) • Fan • Hair dryer • Washing machine & dryer • Child-friendly • Pets allowed • Public parking (free and paid) outside the village walls • Check-in from 4.00pm, Check out before 10.00ambrbrExtra costsbrHeating = €15 per day from October 15 to April 15, payable at the time of booking;brSmall pets allowed = €15 per stay, payable at the time of bookingbrbrLocationbrThe house is located in the centre of the village, in the pedestrian area, opposite the Church of San Salvatore and next to the ancient underground walkway of Via delle Volte, which runs along Castellina’s medieval walls. The square has several restaurants and bars where visitors can soak up the atmosphere.brbrThe location is ideal for a relaxing holiday with family and friends. It makes an excellent base for gastronomic itineraries through the vineyards of Chianti. For self-catering, the local markets are a treasure trove of the very best local produce, from vegetables to cheese and olive oil.brbrSome of Italy’s most beautiful cities and villages are within easy reach. Florence, is just 45 minutes away and offers some of the finest galleries, museums and architecture in the world. As do the cities of Siena (30 minutes) and Pisa, with its Leaning Tower (1 hour, 30 minutes) and San Gimignano (40 minutes), famous for its many towers.brbrThe closest airports are Florence, which is a 45 minute drive, and Pisa, which is 1 hour 25 minutes away.
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$225.59

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Private Vacation Home

Chianti Classico Home Panoramic View 4, Castellina in Chianti, Italy

Castellina In Chianti, Castellina in Chianti, Italy

Explore Tuscany and the famous Chianti Classico region from this authentic Tuscan house in the heart of Castellina in Chianti. This beautifully restored old townhouse sleeps 4 people and makes an ideal base for friends or family who want a holiday that combines gastromony, vineyards and the historic cities of Tuscany.brbrThe front door is just off the main square, and reached through a peaceful, private garden, with magnificent views over the neighbouring countryside. Elegant stairs lead from the entrance hall up to the first-floor living area. With terracotta floors and antique furniture, the apartment retains its original charm. The spacious living room is furnished with a sofa and armchairs, an open fireplace and a Smart TV. The adjacent kitchen/dining area includes a dining table and a well-equipped kitchen. The kitchen includes a cooker hob, oven, microwave, dishwasher, fridge and coffee machine.brbrSleepingbrThere are 2 lovely bedrooms, each tastefully decorated with antique furniture including a double bed, wardrobe and chest of drawers. Each bedroom has an en suite bathroom.brbrBathroomsbrThe 2 en suite bathrooms are all equipped with a shower, basin, bidet and WC.brbrAdditionalbr• Free Wifi • Smart TV • Private, fenced garden • Central heating (available 15th October to 15th April) & open fireplace (wood not included) • Fan • Hair dryer • Waste disposal • Washing machine & dryer • Child-friendly • Pets allowed • Public parking (free and paid) outside the village walls, car essential • Check-in from 4.00pm Check out by 10.00ambrbrExtra costsbrHeating = €15 per day from October 15 to April 15, payable at the time of booking;brSmall pets allowed = €15 per stay, payable at the time of bookingbrbrLocationbrThe house is located in the centre of the village, in the pedestrian area, opposite the Church of San Salvatore and next to the ancient underground walkway of Via delle Volte, which runs along Castellina’s medieval walls. The square has several restaurants and bars where visitors can soak up the atmosphere.brbrThe location is ideal for a relaxing holiday with family and friends. It makes an excellent base for gastronomic itineraries through the vineyards of Chianti. For self-catering, the local markets are a treasure trove of the very best local produce, from vegetables to cheese and olive oil.brbrSome of Italy’s most beautiful cities and villages are within easy reach. Florence, is just 45 minutes away and offers some of the finest galleries, museums and architecture in the world. As do the cities of Siena (30 minutes) and Pisa, with its Leaning Tower (1 hour, 30 minutes) and San Gimignano (40 minutes), famous for its many towers.brThe closest airports are Florence, which is a 45 minute drive, and Pisa, which is 1 hour 25 minutes away.
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$129.37

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Apartment

Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Castellina In Chianti, Castellina in Chianti, Italy

The apartment Al Poggio Della Capannina in Castellina in Chianti is the perfect accommodation for a stress-free holiday with your loved ones. The 50 m² property consists of a living room, a well-equipped kitchen, 2 bedrooms and 1 bathroom, and can accommodate up to 4 people. Additional amenities include high-speed Wi-Fi (suitable for video calls) and a dedicated workspace for home office. A baby cot is available and the apartment is equipped with air conditioning. This holiday home also offers a private outdoor area with a garden and barbecue facilities.brbrbrbrThe accommodation is ideally located in the heart of Chianti, just a short walk from the town centre, where you can find excellent restaurants and taste local wines. One of the best ice cream parlours in the region is also nearby. The location is quiet and peaceful, ideal for relaxing and enjoying the unique atmosphere of Chianti, with a splendid view stretching from Amiata to Val d'Elsa and to San Gimignano. It is the perfect place to admire Tuscan sunsets.brbrbrbrThere is one parking space on the property and free street parking is available.brbrA maximum of 2 pets is allowed.brbrSmoking and parties are not permitted.brbrThe property provides guidelines for proper waste separation; further information is available on site.brbr- Pet allowed payment 15,00 € per pet
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$144.29

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Private Vacation Home

Casa Chiara by Interhome

Castellina In Chianti, Castellina in Chianti, Italy

Modern house Casa Chiara, 2 storeys, built in 2009. 300 m from the centre of Castellina in Chianti, in a sunny position, excellent location: right in the centre but still quiet, west facing position. Private: terraced garden, 40 m2 (not fenced), parking on the premises, single garage at the house. Shop 300 m, grocery, supermarket 500 m, restaurant 300 m, bar, bakery 300 m, pedestrian zone, 3 minute walk to the centre, bus stop 200 m, sandy beach Cecina Mare 85 km, outdoor swimming pool 3 km, indoor swimming pool 12 km, thermal baths Rapolano Terme 50 km. Golf course (18 hole) 35 km, walking paths from the house 500 m. Nearby attractions: Radda in Chianti 12 km, Greve in Chianti 20 km, Siena 26 km, San Gimignano 34 km, Firenze 50 km, Pisa 100 km. Please note: baby equipment (included).brCasa Chiara, 3-room house 75 m2 on 2 levels, west facing position. Practical and modern furnishings: living/dining room with dining table and TV (flat screen), wood-burning stove. Kitchen (oven, dishwasher, 5 gas rings, toaster, kettle, microwave, freezer, electric coffee machine, Capsules for coffee machine (Nespresso) extra). Exit to the terrace. Sep. WC. Upper floor: 1 double bedroom with air conditioning. Exit to the balcony. 1 children's room with 2 beds (90 cm, length 200 cm), air conditioning. Bath/bidet/WC. Heating, air-conditioning. Parquet floors, natural stone floors. Terrace 20 m2 partly roofed, west facing position. Terrace furniture, barbecue, deck chairs (2), box-room. Very beautiful panoramic view of the countryside. Facilities: washing machine, dryer, iron, children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). Parking (1 car), garage on the property (1 car) at the house. Please note: suitable for families. Non-smokers only. Maximum 1 pet/ dog allowed. Private entrance. No mandatory extra charges to be paid on-site except for local tax. Bedlinen, towels, final cleaning and all energy costs are included. IT052005C2YKG73XN2brbrIncluded in price:brAir-conditioningbrERV cancellation insurancebrPower costsbrHeatingbrFinal cleaning (Basic cleaning is always carried out by the guest)brGarage 1xbrLaundry (initial supply of bed linen and towels)broutdoor parking spacebrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / Highchairbrbr #IT5252.660.1
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$1193.84

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Cottage

Casale Monte

Castellina In Chianti, Castellina in Chianti, Italy

The cottage in Castellina in Chianti has 6 bedrooms and has capacity for 12 people. The cottage is 480 m². The farmhouse, completely renovated, is located within a large property that extends over an area of ​​about 460 hectares near Castellina in Chianti. Careful restoration work has brought it back to its ancient splendor. This ancient and majestic farmhouse stands in a dominant position on the hills of the Chianti Senese. From the house you can enjoy a splendid view of the surrounding countryside where vineyards and olive groves alternate. Careful restoration has returned the house to its ancient charm. Central position with respect to the Chianti area and the art cities of Siena and Florence.Within the estate there are alternating vineyards, olive groves and wheat fields, protected by woods and scrub. 5 km from Castellina in Chianti (food shops, tennis), 15 km from Poggibonsi (all kinds of shops), 20 km from Siena and San Gimignano, 50 km from Florence. Tennis 15 km, riding stables 15 km.The house is characterized by a garden and outdoor areas equipped with portable barbecue, equipped loggia and closed L shaped swimming pool measuring 12 x 8 m.On the ground floor:- large equipped loggia- living room with satellite TV and adjacent second living room with fireplace that opens onto the dining area- kitchen equipped with oven, dishwasher, freezer, microwave oven, American coffee maker and toaster- 1 double bedroom with single beds- 2 bathrooms with shower- laundry room with washing machineOn the first floor:- large living room from which you access 3 double bedrooms and 1 bedroom with two single beds, all with bathroom with shower- 1 living room with fireplace from which you access 1 double bedroom with bathroom with shower. Air conditioning in the bedrooms on the first floor.pets are allowed for a fee (Euro 30/animal/per week).Arrivals must be between 15:00 and 19:00.Guests have access to the farmhouse, the equipped garden and the swimming pool, open from May 1st to October 13th.Access via 300 m of dirt road.Other things to keep in mindAdditional costs to be paid on site:-Tourist tax per person/day: 2.00 EUR for 7 daysSecurity deposit: 150 euro at arrival and return and the departure assuming any damageon request: extra bed ( single bed) 90 euro per stay.baby bed on request. ( the first is included , the second 35 euro per stay.animal accept ( 30 euro per pets): Pets must be approved at the time of request and are the owner's responsibility. the villa is not fenced and maximum care of the animal and respect for the house is required
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Bath 7

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