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Villa La Cipressaia: An Authentic Tuscan Escape in Chianti

Castelnuovo Berardenga villa with kitchen

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Photo gallery for Villa La Cipressaia: An Authentic Tuscan Escape in Chianti

A stone building with a garden, a small table with chairs, and a dog.
A courtyard with stone walls, potted plants, and a staircase leading to an upper level.
A stone courtyard with a wooden pergola, potted plants, and a metal gate.
A kitchen with wooden cabinets, a dining table, and a large window.
A swimming pool with two blue lounge chairs, surrounded by a well-maintained lawn and trees.

Reviews

9.6 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Pet friendly
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Castelnuovo Berardenga, Siena
  • Place, Felsina
    ‪8 min drive‬
  • Place, Vittorio Alfieri Theater
    ‪9 min drive‬
  • Place, Castle of Brolio
    ‪12 min drive‬

Room options

About the neighborhood

Castelnuovo Berardenga

In Castelnuovo Berardenga .Within 6 miles (10 km) of this villa, you'll find Vittorio Alfieri Theater and Felsina. Piazza Marconi and Villa a Sesta Polo Club are also within 6 miles (10 km).
View more Villas in Castelnuovo BerardengaOpens in a new window

What's nearby

  • Felsina - 8 min drive - 3.8 miles
  • Vittorio Alfieri Theater - 9 min drive - 3.8 miles
  • Landscape Museum - 9 min drive - 3.8 miles
  • Piazza Marconi - 12 min drive - 4.2 miles
  • Castle of Brolio - 12 min drive - 6.7 miles

Getting around

  • Castelnuovo Berardenga Station - 19 min drive

Restaurants

  • ‪Bengodi Enoteca & Cucina - ‬12 min drive
  • ‪Bar Castelnovo - Da Salvatore - ‬11 min drive
  • ‪Sira e Remino - ‬7 min drive
  • ‪AnoniMax Ristorante & Bistrot - ‬12 min drive
  • ‪La Taverna della Berardenga - ‬9 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Villa La Cipressaia: An Authentic Tuscan Escape in Chianti

Slow mornings, rolling vineyards, peaceful gardens and the timeless beauty of Tuscany.

Welcome to Villa La Cipressaia, a charming stone farmhouse retreat nestled among vineyards, olive groves and the picturesque hills of Chianti, just a short drive from Siena.

Here, life moves at a gentler pace. Wake up to the sounds of nature, enjoy breakfast in your private garden, discover beautiful medieval villages and savour a glass of local wine while admiring the countryside.

Your Private Tuscan Retreat

Villa La Cipressaia occupies an independent portion of a traditional Tuscan farmhouse, thoughtfully restored to preserve its authentic architectural character.

The accommodation is arranged over two floors and comfortably welcomes up to six guests.

The ground floor features a cosy living room with fireplace, satellite TV, Wi-Fi and a double sofa bed, together with a dining area and fully equipped kitchen with oven and dishwasher. A guest toilet is also available.

Upstairs, you'll find a double bedroom with a charming covered loggia, a twin bedroom and a bathroom with shower.

Traditional furnishings, stone details and a welcoming atmosphere create the feeling of an authentic Tuscan country home.

A Beautiful Private Garden

One of the most delightful features of Villa La Cipressaia is its large, fully fenced private garden, surrounded by the natural beauty of the Chianti countryside.

Reserved exclusively for your use, this peaceful outdoor space is perfect for relaxing, reading, sharing leisurely meals or simply admiring the views.

The charming stone courtyard and furnished outdoor dining area invite you to enjoy long Tuscan evenings beneath the open sky.

Swimming Pool and Countryside Views

Guests can enjoy a lovely 14 × 6 metre swimming pool set in a separate landscaped garden.

The pool is shared with the other residents of the farmhouse and is available during the seasonal opening period, from 10 AM to 1 PM and from 3 PM to 6 PM.

The villa's private garden remains entirely reserved for you.

Explore Chianti and Tuscany

Villa La Cipressaia is ideally situated for discovering the best of Tuscany.

The enchanting medieval village of San Gusmè is just 2 km away, with restaurants, a wine bar and local shops.

Siena is approximately 25 km from the villa, while Florence, San Gimignano, Montalcino, Pienza, Montepulciano and many other historic destinations make wonderful day trips.

The surrounding area is also home to celebrated wineries, olive oil producers, traditional restaurants and unforgettable countryside scenery.

Whether you're planning a romantic escape, a family holiday or a relaxing getaway with friends, Villa La Cipressaia offers an inviting setting to experience the beauty and traditions of Tuscany.

Come for the views, stay for the peace and discover your own little corner of Tuscany.

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  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
4.8 out of 5, Exceptional, 219 reviews
$254 nightly
The price is $288
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Total with taxes and fees
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Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the villa: WiFi

Parking and transportation

  • Car required
  • Parking on site

Kitchen

  • Dishwasher
  • Microwave
  • Refrigerator

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathroom

  • 3 bathrooms

Living spaces

  • Fireplace
  • Wood stove

Entertainment

  • Books
  • DVD player
  • Stereo
  • TV with cable/satellite channels
  • Video library

Outdoor areas

  • Balcony
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Pets

  • Pet friendly

Suitability/Accessibility

  • Designated smoking areas

Services and conveniences

  • Phone

Location highlights

  • In a rural location
  • Near a health/beauty spa
  • Near a zoo
  • Near an outlet shopping mall

Things to do

  • Basketball nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Mountain biking nearby
  • Rock climbing nearby
  • Sailing nearby
  • Swimming nearby
  • Theme park nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: 25€ per week for pet

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking allowed: in designated areas

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited.

Property Registration Number IT052006C2J9CSCS24

We should mention

  • All guests (including children) need to be present at check-in to show their government-issued photo ID or passport.
  • Onsite cash transactions can't exceed USD 5000, due to national regulations. For more details, please contact the property using information in the booking confirmation.
  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

Charming Villa Large Pool Garden Close to Siena Chianti Area

Frequently asked questions

Does Charming Tuscany Villa with magical Garden, shared pool, Chianti Area have an airport shuttle?

Airport shuttle services are not available at this villa.

Does Charming Tuscany Villa with magical Garden, shared pool, Chianti Area offer free breakfast?

This villa does not offer free breakfast.

Is there a casino at Charming Tuscany Villa with magical Garden, shared pool, Chianti Area ?

No, there is no casino at this villa.

What time is check-in at Charming Tuscany Villa with magical Garden, shared pool, Chianti Area ?

Check-in begins at 3:00 PM.

Is there free parking at Charming Tuscany Villa with magical Garden, shared pool, Chianti Area ?

Free parking is not available at this villa.

Does Charming Tuscany Villa with magical Garden, shared pool, Chianti Area have a pool?

Yes, there's a pool.

Does Charming Tuscany Villa with magical Garden, shared pool, Chianti Area have a spa?

There are no spa services available at this villa.

How close is Charming Tuscany Villa with magical Garden, shared pool, Chianti Area to downtown Castelnuovo Berardenga?

This villa is 2.3 mi away from Castelnuovo Berardenga.

Villa La Cipressaia: An Authentic Tuscan Escape in Chianti Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 50 out of 61 reviews
Rating 8 - Good. 6 out of 61 reviews
Rating 6 - Okay. 3 out of 61 reviews
Rating 4 - Poor. 2 out of 61 reviews
Rating 2 - Terrible. 0 out of 61 reviews

9.2/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

Definitely will visit again!
Stayed 4 nights in Jun 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and beautiful oasis in Tuscany

We had a lovely stay a few weeks ago in this charming old stone house with gorgeous gardens surrounded by vineyards and olive groves. A great base as we explored Tuscany for 4 days.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

For those who want to experience the taste of life in Tuscany

Great host, location as we wanted in Tuscany. We had villa for only our family and it was enjoyable. It is a good WiFi there, TV, kitchen. And everything you need.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great getaway

An amazing escape in the Tuscan countryside. The pool and views from it were jaw-dropping. Close enough to venture out to some sights but far enough away to feel like you are in the country. We had some amazing meals in the nearby small towns. Still dreaming about our visit.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Tuscany

My family and I had a lovely stay. Lots of places to visit and wonderful garden for the children to play. They loved the pool, and the little cat that wanted to be apart of the family. Thank you for a lovely time.
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
For a true Tuscan experience, this location is perfect. You can find your own private spot within the stunning garden, surrounded by rolling, vine-covered hills and lines of cypress trees. There's also a great pool for relaxing. If you want to avoid the tourist crowds of bigger towns, this is the ideal retreat. You'll find plenty of lovely villages and great restaurants within a short drive. We're so thankful to Gina and Bianca for their wonderful hospitality.
Stayed 10 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

It was like being in an art filled environment surrounded by vineyards.

Visually a feast for our eyes
Stayed 5 nights in Jun 2019
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location

Beautiful property, gardens and pool. Nice place to relax. 10 minute drive to a quaint town with groceries. Only 35 minutes to Sienna .
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tuscan Idyll

5 lovely days. Pool was a necessity. Beautiful accommodation and garden and very well equipped kitchen. Visitors info probably needs an update.
Stayed 5 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great views!

Lovely spot with gorgeous views. It proved to be a good location to explore Tuscany. When we arrived it was a chilly day and we were invited to fire up the boiler although warned heat was expensive and we would be charged additional for any fuel used so we toughed it out not wanting to deal with it.
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tuscany Beauty

Our stay at Villa Donato was truly a wonder experience. Within and hour or less you can visit many of the enchanting hill towns of Tuscany, such as Castellina, Rodda & Cortona to name a few. If you want to visit the Brunello wine region it is also in that same range of travel. The gardens are amazing and perfect for outdoor dinners & breakfasts. The kitchen is well equipped & very nice for preparing home cooked meals. Our stay was delightful!
Stayed 14 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A gorgeous spot

Aside from being as an absolutely stunning property, I appreciated the fact that the kitchen was well equipped. I find most rentals have almost nothing to cook with. They had everything I needed!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rustic Charm in Tuscany

What a gem in the hills of Tuscany. The gardens are exquisite surrounding the villa with a picturesque view from every window. We also enjoyed the visiting cat who was so friendly and sweet. We cooked all our meals in the kitchen and slept restfully. Would love to return soon.
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Villa

We were both very pleased with this charming villa, set in beautiful countryside about 15 minutes drive from the nearest small town. We loved the rustic feel of the villa with amazing views of the surrounding vineyards. The hosts, while we didnt meet up due to our busy schedules, were fabulous, and great at communicating to ensure we had a wonderful stay. We used the villa here as a base to make day trips to surrounding towns like Assisi, Perugia, San Gimignano and Montepulciano, all towns worth visiting.
Stayed 3 nights in May 2024
Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy
Disliked: Communication

Tuscan vacation villa

This property is amazing, especially during the warmer months. It is as lovely as described. It’s expensive to heat during cooler months. Communication with the property manager was challenging as her English is limited, as is our Italian. The location is central in terms of visiting a variety of hill towns, but remote in terms of finding dinner, especially during the off season.
Stayed 8 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This villa was such a charming place and is so serene and beautiful. We loved being able to cook with a full kitchen and eat our meals on the patio in the garden. We used the villa as a base as we visited wineries and small hill towns, everything was about an hour drive away. The host provided very clear instructions on how to get to the property and on how everything worked in the house. The views and pool were amazing as well. No AC and we had unusually hot temperatures, but there were several fans and there was often a cross breeze. Overall, we really enjoyed our stay and would recommend if you are looking for a quiet, relaxing time in Tuscany.
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely amazing!

We had a wonderful stay. The views and gardens are amazing and the pictures you see online do not do it justice. The views are breathtaking. The home is comfortable and has everything you need. We had 5 people so our teenager had to sleep on the sofa bed in the living room but it wasn’t too bad, It is a convenient location for exploring the Chianti region but is also an amazing property to stay and relax. Bianca was a very responsive host and we enjoyed meeting her mother who greeted us at the property. Overall, our favorite place during our 15 day tour of Italy!
Stayed 5 nights in May 2023
Verified review

6/10 Okay

Liked: Communication
Disliked: Cleanliness, location
The farmhouse/villa is old, but we knew that when we chose this location to rent for our 4-night stay. That said, it could use some deep cleaning. Surface areas and floors were not clean, and there was a bit of a bug issue. We think they were similar to stink bugs, but weren't sure. The mattress in the room I slept in was horrible. My hips hurt every night sleeping on it. It was the smaller of the two bedrooms. My friends slept in the other room and had no issues with their mattress.The location was more remote than we anticipated. It would have been nice to be closer to a town for easier dining out and a market to buy essentials. That’s our fault, though, for not checking this in advance.
Stayed 5 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, location
Disliked: Listing accuracy

Nice but a little disappointed....

Very nice villa in a great, peaceful and scenic location between Sienna and Arezzo. Disappointed because the pool was closed after recent rains though we booked it for the pool and were not notified it would be closed. Pools at other places we stayed in the region were open. Also, prior guests had smoked inside and ashtrays were full tho we let the host know we are allergic to smoke and were told there was no smoking allowed inside. Local wine tasting and restaurants were great, and the villa itself was very pretty.
Stayed 5 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wunderschönes Landhaus. Eingebettet in die Weinberge des Chianti. Sehr nette Gastgeber. Wir werden in den nächsten Jahren sicherlich noch einmal dorthin fahren.
Stayed 8 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jardin magnifique, lieu calme et reposant.
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Erholsamer Urlaub in wunderschöner Gegend

Die Villa ist ein zauberhafter Ort für alle, die Ruhe und Natur genießen wollen. Die Anfahrt ist nur mit dem Auto möglich. Der letzte Streckenabschnitt führt durch eine märchenhafte Zypressenallee. Das Grundstück liegt auf einer Anhöhe mit einem herrlichen Blick auf die umliegenden Weinberge. Die Villa ist in zwei autarke Wohnparteien mit jeweils eigenen Garten aufgeteilt. Der Garten ist groß und hübsch bewachsen. Das Haus ist individuell und gemütlich mit kunstvollem Ambiente. eingerichtet. Die Vermieter, die Familie Gigli, sind sehr freundlich, hilfsbereit und zuvorkommend. Wir haben uns sehr wohl gefühlt und uns mit unseren unmittelbaren Villa-Nachbarn gut verstanden. Insgesamt gibt es hier vier Eigentümerparteien, die den Pool geinschaftlich nutzen. Das hat für uns gut funktioniert. Die Eigentümer/ Bewohner der benachbarten Häuser legen Wert auf ihre Ruhe und die Einhaltung der Pool-Regeln. Dazu gehört auch die Beachtung der Pool-Zeiten für die Gäste (10-13 und 15 bis 18 Uhr). Wir konnten uns damit gut arrangieren, weil wir sowieso viel unterwegs waren.
Stayed 7 nights in Aug 2024
Verified review

6/10 Okay

Liked: Check-in, communication, location, listing accuracy

Die Umgebung ist sehr schön

Das Haus ist wie abgebildet, leider ist es im Haus sehr dunkel und muffig, da es mit sehr vielen Gegenständen vollgestellt ist. Die Umgebung, Landschaft die ganzen kleinen Orte sind sehr schön für Ausflüge.
Stayed 5 nights in Aug 2024
Verified review

4/10 Poor

Liked: Cleanliness, location
Disliked: Communication, listing accuracy

Schönes Haus, doch wichtige Informationen fehlten in Anzeige

Der Aufenthalt war 50/50. Das Haus ist sehr schön. Ruhige, abgelegene Lage, doch es ist Teil eines größeren Hauses mit zwei sehr anstrengenden Anwohnern. Das für uns größte Problem war, dass wir erst bei Ankunft im Haus erfuhren, dass der Gemeinschaftspool nur von 10-13 und 15-18 Uhr zu nutzen ist - und Kinder bis 18 Jahren durch einen Erwachsenen zu beaufsichtigen sind. Dies hat unsere vollständige Urlaubsplanung zunichte gemacht. Leider gab es mit der Vermieterin keine Lösung zu einer Rückzahlung oder kürzerem Aufenthalt. Auch FeWo hat sich um nichts gekümmert. Wir haben somit den Urlaub nach sechs (von 14) Tagen abgebrochen. Wer also denkt er könne den Pool nach Bedarf nutzen, der sollte die Finger von dem Objekt lassen.
Stayed 14 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Décor de rêve

La maison est située dans un endroit magnifique, près de 2 très beaux villages (San Gusmè et Castelnuovo Berardenga). Le jardin est superbe. Un point négatif est l'éclairage dans la maison, et les interrupteurs peu pratiques, difficiles à trouver.
Stayed 7 nights in Jul 2023

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