Castiglione del Lago Villas ￥14,446

A historic square with a fountain, stone steps, and traditional buildings with balconies and shutters.

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Our top choices for Castiglione del Lago villas

A terrace with a table and chairs, a view of the sunset, and a stone building.

1. Villa Graziella, Romantic Perugia

La Valle

Rob B.

￥35,022 total

includes taxes & fees

Oct 25 - Oct 26

A stone building with a courtyard, outdoor seating, and a view of the hills.

2. Villa San Biagio – Luxury villa, newly renovated villa with Pool, stunning views, pool & airco

Città della Pieve

"Pros: My wife & myself loved everything about this house! From what it looked, the house has been recently fully renovated. All bedrooms are spacious & nicely decorated. There are 3 living rooms! we spent an evening playing cards in the library. The pool area is very pleasant, the view of the valley is absolutely magical! The historical village of Citta della Pieve is only 5-10 min away by car. Supermarket is close by! We will definitely stay longer next time. Cons: nothing! everything was...

Anonymous traveler

￥241,447 total

includes taxes & fees

Oct 25 - Oct 26

A well-lit courtyard with a stone pathway leading to a building with a large arched entrance.

3. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

Cortona

￥953,837 total

includes taxes & fees

Oct 28 - Oct 29

4. Godiluva, Weinvilla

Toscana

￥663,012 total

includes taxes & fees

Oct 30 - Oct 31

A two-story building with balconies, outdoor seating, and potted plants.

5. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

￥14,446 total

includes taxes & fees

Oct 27 - Oct 28

A stone wall, a round table with chairs, a bowl of fruit, and a glass of juice.

6. Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Cortona

￥319,821 total

includes taxes & fees

Oct 25 - Oct 26

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

7. Il Poggio dell'Eremita

Sinalunga

Paul Q.

￥28,241 total

includes taxes & fees

Oct 27 - Oct 28

A rustic stone building with a dirt path leading to it, surrounded by greenery and trees.

8. Il Granaio, Villa for 6 people with heated jacuzzi and pool in the garden

San Venanzo

Richard N.

￥62,119 total

includes taxes & fees

Oct 25 - Oct 26

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

9. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Torrita di Siena

"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."

Nate D.

￥381,499 total

includes taxes & fees

Oct 25 - Oct 26

A patio with a table and chairs, a large umbrella, and a vase of flowers.

10. Villa Cielo- Cignella Resort Tuscany Accommodation

Trequanda

￥50,864 total

includes taxes & fees

Oct 26 - Oct 27

A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

11. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Trequanda

￥41,291 total

includes taxes & fees

Nov 6 - Nov 7

A stone-walled patio with wicker furniture, a table, and a view of a green landscape.

12. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

"Incredible stay! Property was beautifully restored and outfitted, and immaculately clean when we arrived. The host was very responsive, helping us bring in a local chef and responded quickly to our various questions during our stay. The heated pool was wonderful. The property was the right size for seven guests. We hope to return because six nights here wasn’t enough! I wish there was an option to give higher than five stars!"

Marshall W.

￥113,343 total

includes taxes & fees

Oct 25 - Oct 26

A swimming pool with a sunset view, surrounded by trees and a distant mountain range.

13. Casa Boschetto, villa with swimming pool sleeps 9

San Venanzo

Georgia A.

￥85,227 total

includes taxes & fees

Oct 25 - Oct 26

A stone building with a tiled roof, a paved entrance, and potted plants.

14. Antica Filanda 6 - Three Bedroom Villa, Sleeps 6

Arezzo

￥60,801 total

includes taxes & fees

Nov 1 - Nov 2

A covered patio area with a pergola, outdoor seating, and a view of the countryside.

15. Villa San Casciano – Private Pool, Village and Thermal Baths within Walking Distance

San Casciano dei Bagni

￥71,344 total

includes taxes & fees

Nov 8 - Nov 9

A two-story building with a balcony, outdoor seating area, and string lights.

16. VILLA IL MATTO with a saltwater pool, spa, and sauna

Toscana

￥102,272 total

includes taxes & fees

Oct 25 - Oct 26

A large, red-roofed villa surrounded by lush green fields and rolling hills.

17. '...a delicious farmhouse in the countryside where only the wind blows...'

Campiglia d'Orcia

"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...

Li-Shen L.

￥254,626 total

includes taxes & fees

Oct 27 - Oct 28