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Castellina In Chianti Rentals

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5,071 Houses

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$174

Rental house in the centre of this Chianti village

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$90

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$237

Lovely apartment in a small winery

Castellina In Chianti barn

2 bedrooms / 1 bathroom / sleeps 4

“The real heart of Tuscany, a dreamholiday” For many years we have spent every summerholiday in Italy. It took only little time trying out various locations before we realized that the Casina at Setriolo was the perfect place and since then we haven't been anywhere else. The place is beautiful, quiet, romantic. The views from the terrace breathtaking. The garden lush and colourful, the swimming pool surrounded by lavender and green hedges. The house itself offers everything you need, it is compact, practical and yet full of character. And situated in the heart of the Chianti region of Tuscany all the main attractions are nearby. And even after having bought our own house in Umbria, we will go on visiting Setriolo for the dear owners and the beautiful memories.

Price per night from

$166

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

1 bedroom / 1 bathroom / sleeps 2

“Very Romantic and Relaxing” Podere Patrignone, is a very well managed holiday/vacation destination. Simon and Verity (owners), went to great lengths to make sure ours and other guests stays we're relaxing and enjoyable. Always available, but rairly needed, they have created an "old world charm" and very natural feel to their quiet olive orchard. Whether it's a romantic getaway (ours was our 10th wedding anniversary), a quiet place to retreat and relax, or just a quaint Tuscan "centrally" located place to stay, we highly recommend it. Everything on their website was exactly as advertised! What isn't as highly advertised, but left to us to tell about, is the care and passion Simon and Verity have for making this such a special place to stay. And don't miss the weekly group dinner. Verity goes all out for that, and it's a delicious Tuscan style feast with a wonderful group of people! We can't wait to return!

Price per night from

$194

Authentic 3 Bedroom Farmhouse

Castellina In Chianti b&b

3 bedrooms / 2 bathrooms / sleeps 8

“The best and most relaxing vacation ever” As two couples, Poderi Val Verde's restored farmhouse was indeed rustic, but was perfect for us: adjoining suites each with a kitchen and patio overlooking the stunning grounds, one with a living room and fireplace, the other with a fantastic sunroom overlooking the grounds and pool. We stayed for our full 2 week visit and were thrilled with our choice of living on a working farm of over 200 hectares with a 350 year history. Our quarry stone home was clean, comfortable and perfectly located to facilitate our day trips to nearby villages-to neighboring Castellina in Chianti, as well as Siena, Florence, Poggibonsi, Greve, and Panzano where we participated in their annual wine festival. Around every corner of the road there was another breathtaking vista each arguably better than the last. We had our big Italian meal of the day wherever we were early in the afternoon and made a light dinner in our kitchen most evenings, eating on the patio with candle lights and wine listening to the sounds of wild boars, deer and wolves in the hillside and our hostesses' dogs keeping them all at bay. Most mornings we watched the sun rise over the valley, prepared a quick breakfast then usually stopped mid-morning for cappuccinos. Our kitchens were well equipped, however the lighting didn't meet our standards, easily solvable by task lights ... but,if that's our only complaint!!! Our hostess, Ulrike, runs the farm alone, feeds the sheep, chickens, ducks, dogs, cats and countless kittens who were always underfoot and also feeds her guests a Welcome Dinner Feast that shouldn't be missed - for the food and for the opportunity to meet new friends. Ulrike was always there to help us, make suggestions and share some wine or her homemade jams. By the end of our visit, she was no longer our hostess but a huggable friend. My well-traveled wife called it the best and most relaxing vacation of her life. When we return, we'll stay there again.

Responds fast! avg. 1 hour 21 minutes

Price per night from

$336

Guidi

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$92

"La Tana" - 2BR /1BA ground floor apartment with large terrace

Castellina In Chianti farmhouse

2 bedrooms / 1 bathroom / sleeps 4

“Location, location, location!” The complete Chianti valley, rustica experience of staying in comfortable stone cottages surrounded by beautiful gardens - the irises were blooming while we were there - plenty of space for kids to run and play while the parents kick back and relax around the pool or on their terraces. Ulrike is a very generous host, full of information and stories about her beloved Toscana. Her dinners are well worth the experience to get to know your fellow travellers as well as part taking in genuine cucina and always great music playing in the background. Every Tuscan tourist high spot is within 1 or 2 hours drive away and if you enjoy driving, you will enjoy the journey as much as the destination. Castellina is a beautiful village and worth many visits to enjoy local produce including the famous Chianti Classico and the best gelato in Italy. Whether you are travelling as a family, group of friends, couple or as an individual this is a great place to stay- even dogs are welcomed as long as they remember Ulrike's dogs are in charge!

Responds fast! avg. 1 hour 21 minutes

Price per night from

$154

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A totally relaxing rural Tuscan retreat.” Podere Patrignone is a beautifully rustic, rambling farmhouse, secluded in its own woods. There are a number of properties for rent within the complex, from compact and bijou, to spacious and open, all with their own particular charm. It makes a wonderful base for touring, being within easy reach of Florence, many Tuscan hilltowns and villages, and stunning Sienna. Simon and Verity are charming, helpful and very friendly hosts, as are their family, and of course, their dogs!! The weekly "home cooked" meal is a great opportunity to sample Verity`s cooking, and meet your fellow guests. The position of the complex within the landscape, is superb, and there are wonderful views from the terrace and pool area, over surrounding olive groves and vineyards. There are a number of excellent restaurants within very easy reach, where local food and wine can be enjoyed. I would also suggest visiting local wine producers, of which there are many. My wife and I have stayed at Patrignone for two weeks, in both 2011 and 2012, and we would not hesitate to recommend this lovely destination. Do not be expecting a five star hotel, that is not what Patrignone is about!! It is, as Simon says, a work in progress. However, I fail to see how a stay here, could ever disappoint. Truly Tuscan in every sense.

Price per night from

$283

"Il Giardino" - 3BR/3BA apartment on Tuscan Estate in the Chianti

Castellina In Chianti apartment

3 bedrooms / 3 bathrooms / sleeps 9

“Lovely home cooking courses” My wife and I came to Chianti for our honeymoon, and spent a thoroughly enjoyable evening doing a cookery course with Ulrike. The meals were traditional Tuscan fare and delicious, whilst easy enough to follow so that we will have confidence to do them again. It also made a big difference that the cooking was very hands on - Ulrike encouraged us to get stuck in and enjoy ourselves. All in all - good company and good value, recommended.

Responds fast! avg. 1 hour 21 minutes

Price per night from

$264

2 Bedroom Cottage in Castellina in Chianti

Castellina In Chianti cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Homely days in Chianti” Very nice location - quiet and ideal for relaxation - polite hostess - tasteful furnished old stone house with modern comfort in kitchen and bathroom - wonderful situated (all the beautiful spots in Chianti are nearby). We would like to return and say thank you to Ulrike. I.Leitner, Salzburg

Responds fast! avg. 1 hour 21 minutes

Price per night from

$203

Belmonte House

Castellina In Chianti house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$329

Tuscany Apartment in Old Chianti Farmhouse

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$150

2 Bedroom Stone Cottage Rental in Chianti Countryside

Castellina In Chianti cottage

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful” We had a excellent stay. It was very clean, comfotable and beautifull.

Price per night from

$135

Luxury 2 bedroom Tuscan Villa

Castellina In Chianti house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$213

Fontani

Castellina In Chianti house

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$145

Farmhouse Rental in Tuscany, Castellina Scalo - Rosalia 3

Castellina In Chianti farmhouse

4 bedrooms / 3 bathrooms / sleeps 8

“Kim's review of Farmhouse Rental in Tuscany, Castellina Scalo -” Onsight staff was helpful and the wines and olive oil were delicious....there is even a sketch of the house on one of labels called Spazzavento. The view, tranquil setting, wildlife pheasant, wild boar, quail, proximity to charming Castellina in Chianti, ability to experience life on a working wine-olive oil estate, easy access to Tuscan hill towns, as well as Siena and Florence, were all highlights of our stay! The house is in the heart of Chianti wine country and close to many picturesque hill towns. We enjoyed taking day trips to towns like Monteriggioni, Radda, Greve, Siena, Cortona, Volterra, Montepulciano, Montalcino, Arezzo and of course Florence.

Price per night from

$200

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

7 bedrooms / 7 bathrooms / sleeps 14

“Outstanding Tuscany Villa” We stayed at Podere Patrignone for 7 days in October 2012. We were a party of 4 couples from the USa. We had done a lot of research in finding a villa that would provide what we thought would be the ultimate Tuscan experience; Podere Patrignone did that. We stayed in the main house and occupied 4 of the bedrooms. The accommodations were great, much like staying at a friend's country home. Each bed room has its own private bath accessed from the bedroom, not a hallway. There is a large, fully equipped kitchen where we spent most nights playing cards, reading, etc. We purchased breakfast 3 days and participated in the dinner one day. All meals were great and highly recommended. We went to many of the restaurants suggested by our hosts and I must say they were all excellent. My recommendation is to follow their recommendations; they will not steer you wrong. Speaking of our hosts, they were great. Simon and Verity are great hosts and were always available to make suggestions, etc. We ran into them most days somewhere on the property and they always had time to stop and chat for a bit, even though we knew they were busy. When reading the reviews on Podere Patrignone you will note almost all are very positive but that a few are not as positive. Remember this - you cannot please everyone. If you are looking for a authentic Tuscany villa, great hosts and an excellent location, you will love Podere Patrignone. All of us in our party did. My wife and I still talk about our week's stay and would love to return some day.

Price per night from

$587

humiliated

Castellina In Chianti house

5 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$234

Farmhouse Rental in Chianti Area of Tuscany - Villa Adelina

Castellina In Chianti farmhouse

5 bedrooms / 6 bathrooms / sleeps 10

“Greg 's review of Farmhouse Rental in Tuscany, Castellina in Chi” Wonderful. The property was beautiful, well cared for, and very comfortable. The seclusion, privacy and beauty. It was also very quiet in the house. Beautiful, but still close driving distance to services.

Price per night from

$468

Villa Beba 6

Castellina In Chianti villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$273

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

15 bedrooms / 15 bathrooms / sleeps 33

Price per night from

$1,635

Farmhouse Rental in Tuscany, Castellina Scalo - Rosalia 2

Castellina In Chianti farmhouse

3 bedrooms / 3 bathrooms / sleeps 7

“Martha's review of Farmhouse Rental in Tuscany, Castellina Scalo” Everyone we met was delightful and helpful. If you are looking for someone to hold your hand and guide you every day, then this isn't' the place for you. If you want to be on your own, but can find someone down the road in the office if needed, then this is the place for you. After we checked in and got the key that first day, we did not see anyone until it was time to check out at the end of the week - by our choice. Location was Divine! Beautiful views, plenty of space. The living room was a great place for all of us to gather and talk about the day's events and plan for the next day. Kitchen was used every day - well equipped. We had 6 people staying in the villa and we never felt crowded or in each other's way. Breakfast on the front patio overlooking the vineyards - or sipping wine at sunset was a favorite spot. Extra blankets kept us cozy as nights; it got cool mid-October. Heaters were provided but we never had to use them. The fireplace was used and greatly appreciated. Proximity and easy access to historical towns. The actual property was enormous. We walked around olive trees and grapevines as far as we could see. A quaint little country road was pleasant to walk along and explore the area.

Price per night from

$175

Braccagni

Castellina In Chianti apartment

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$166

Carraretto

Castellina In Chianti apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

Villa Montespertoli

Castellina In Chianti house

5 bedrooms / 7 bathrooms / sleeps 10

Price per night from

$427

Visentini

Castellina In Chianti apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$47

woods

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$92

Villa Arnica B

Castellina In Chianti house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 minutes

Price per night from

$232

Farmhouse Rental in Tuscany, Castellina Scalo - Rosalia 1

Castellina In Chianti farmhouse

4 bedrooms / 4 bathrooms / sleeps 9

“Judson's review of Farmhouse Rental in Tuscany, Castellina Scalo” I would highly recommend this property and I would love to have stayed longer. Given the opportunity I would love to return to it. The owner told us that the week we were there was the last of their rental season and offered to let us stay a few days longer than the original week at no charge. I would have liked to take them up on their offer, but our schedule did not allow it. If you are looking for a wonderful peaceful vacation in Tuscany, this is the place to be! The location was wonderful. The peace and quiet of the area was exceptional. The size of the rooms in the villa was amazing. Everything was in great condition and the owner even had a fire burning in the living room upon our arrival, since it was a chilly day. They also provided two bottles of their own estate wine and a bottle of their estate olive oil. The infinity pool was beautiful. Although it was too cold to get in, it was wonderful sitting by the pool side sipping wine and eating cheese. The little hill towns in the vicinity were great to visit. Castellina in Chianti is just down the road and has much to offer from good restaurants and good views to basic shopping essentials. The wine shops got a lot of our business.

Price per night from

$273

Traditional apartment with pool, table tennis, BBQ

Castellina In Chianti apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

2 bedroom Tuscany apartment with communal pool

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$232

Casa Sibilla D

Ricavo house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 minutes

Price per night from

$182

Villa Isabelle

Castellina In Chianti villa

7 bedrooms / 9 bathrooms / sleeps 14

Price per night from

$998

Castellina in Chianti 2 bed apartment with pool

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$257

Bettini

Castellina In Chianti house

6 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$250

Tuscany 2 bedroom apartment with pool

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$219

Castellina in Chianti 1 bed apartment with pool

Castellina In Chianti apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$258

Viewing 38 of 5,071
rentals in Castellina In Chianti

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Top Destination reviews

6 Bedroom Countryside Villa with Expansive Views
outstanding property and owners!!!

Needed to write up how amazing this property was... if you want a true tuscany experience this is the place to go!!! most outstanding property, surrounded with views to die for of vineyards and olive groves. It is a wine producing property, and the owner was kind enough to take us to the vineyards and took us through the whole wine making process it was absolutely outstanding. We were 12 people and the villa was totally accomodating, we actually never used half of the space it was spectacular. The owners Simonita and staff were extremely welcoming and saw to our every need. Would rate this as outstanding!!!see more
Farmhouse Rental in Chianti Area of Tuscany - Casa Luciana
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I could not imagine a better value for the money nor a more relaxing place in all of Tuscany. With three generations of our family in one house, I expected some calamity. The layout was fantastic with enough areas to keep the kids separated from one another when necessary. The entire house felt designed by us, for us. The vistas from the patio and the pool area are breathtaking. Right in the heart of Tuscany. Under an hour to Florence, Siena, Radda, San Gimignano, etc.see more
Charming One Bedroom Cottage in the Chianti Hills of Tuscany
Peaceful and Beautiful

This was the perfect place for a 10 day stay in Chianti. Le Ripe was just what we wanted. Le Fienile had everything that we needed. The cottage was spacious and comfortable. The views were amazing. A yellow climbing rose and a clematis montana, in full bloom, were growing on the outside of the cottage. The herb garden was beside the door. How wonderful it was to sit on the patio having breakfast or enjoying a glass of Chianti at the end of the afternoon. The location is peaceful and quiet but not far from Panzano. At the bottom of the hill is Le Panzanelle, a Tuscan restaurant , that we really enjoyed. Le Ripe is an excellent base for exploring the area' s beauty, food and wine. Leitha and Fabio, the owners, are lovely and helpful. We hope to return next spring.see more
Lovely apartment in a small winery
Lovely place where the owners make you feel at home

Over the last ten years we spent six times a tjhree week's holiday at the casina. It means we really like this place. The house is very nice and well taken care of and the hospitality and helpfulness of the owners is heartwarming. If you look for a quiet and peaceful spot far from the crowd this is the right place for there are no other guests. We spent many days at the pool and enjoyed the beautiful view from the veranda in the evenings. The casina is a good starting point for visiting a lot of villages and cities in Tuscany. We would definitely recommend the casina, but you need to have a car available for trips and shopping. We will certainly come back again.see more
Ancient villa in Chianti with pool and wonderview
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We really enjoyed our week here. The views and the pool were great and the house delightfully cool despite the heat outside. Everything required was provided. It was also a good base to explore the Chianti wine region, Florence, Siena and San Gimignano. … see more
2 Bedroom Cottage in Castellina in Chianti
Authentic country experience in the Chianti region

Poderi Val Verde is a secluded farm located close to the small town of Castellina in Chianti. There are different types of accommodations on the rustic property with several hiking trails. We chose to stay in the two bedroom cottage since we were traveling with another couple and wanted space to visit. The cottage was clean, quiet and well equipped. The entire property is rustic with no service staff other than the owner, so if you are seeking luxury, this is not the location for you. Unfortunately the weather was colder than expected. Due to local ordinance we could not have heat and the old building was somewhat cold at night. We were not seeking luxury however and wanted to experience the life of the Tuscan people. The owner, Ulrike Eder, was very helpful in steering us toward authentic and unique experiences of the area. As a result we made some wonderful and unexpected memories. We ate the welcome dinner on Saturday and breakfast on the porch daily. The food was well prepared, plentiful and authentic to the region. Castellina is a charming town with surprisingly good restaurants and shops. The location is within an easy drive of Florence, Siena, Lucca and many other towns. We also toured several wonderful wineries and experienced the best of Chianti wines. Overall the trip was exactly what we expected both from the accommodations and the region.see more

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