50 Best Vacation Rentals in Pienza - Holiday Lettings - Cabins

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3,116 Vacation rentals

25

Pienza Vacation lodge rental

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are beautifu …see more

from $120 / night

$834 - $1,290 / week

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from $120 / night

(5) Excellent 

21

Tower rental in Monticchiello

Pienza / Monticchiello

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Ask about children
  • Private garden
In Val d'Orcia is a small medieval village, Monticchiello Pienza, surrounded by walls and protected by four towers; one of these is the "Tower of Charles", which stands at the highest point of the country and enjoys a panoramic view across the valley. unforgettable suns …see more

from $185 / night

$983 / week

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from $185 / night

(1) Excellent 

20

Vacation home in Monticchiello

Pienza / Monticchiello

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden
The "Noble" apartment (so called because it overlooks Montepulciano) Consists of: kitchen with large living room, three double bedrooms each with en suite shower. From the large windows you can admire Montepulciano, home of the noble wine, and the woods of oak and chest …see more

from $246 / night

$1,388 / week

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from $246 / night

34

Vacation villa in Pienza

Province of Siena / Pienza

7 15 7 nights min

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of Pienza. In a short drive there are renowned villages such as Monti …see more

from $290 / night

$2,029 - $3,301 / week

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from $290 / night

(1) Excellent 

22

Vacation villa rental

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Villa Il Mandorlo is one the three Villas of Casali Cellini farm . The Villa is located in the gently rolling Tuscan hills, between the wonderful towns of Pienza and Montepulciano, just a short distance from the thermal baths of Bagno Vignoni. Villa Il Mandorlo is a Vi …see more

from $457 / night

$3,193 - $4,790 / week

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Responds fast!
avg. 3 hours 37 minutes

from $457 / night

(7) Excellent 

23

Vacation apartment in Pienza

Province of Siena / Pienza

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
New lower price - one of the nicest flat in Tuscany 5 star standard !! The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with g …see more

from $185 / night

$1,290 / week

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from $185 / night

12

Vacation apartment rental

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Is a large and flat, like the solar plant that is inspired, located on the first floor of the structure. Its Windows overlook the garden on one side, the other on a characteristic internal courtyard. Has a living room and equipped kitchen (cooking point, fridge, TV), …see more

from $160 / night

$860 / week

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from $160 / night

19

Vacation villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This lovely holiday home in the Middle Ages was probably a resting place for pilgrims travelling on the Via Francigena, that passes nearby. Furthermore, opposite the property is the 13th century Castello di Spedaletto, one of the most important monastic granges of the S …see more

from $225 / night

$1,572 - $2,948 / week

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Responds fast!
avg. 2 hours 4 minutes

from $225 / night

(7) Very Good 

13

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly
The property is located in UNESCO's Heritage Valdorcia in Monticchiello one of most beatifull medioeval village in Tuscany. Between Siena and Rome is a perfect location to enjoy an unforgettable holiday. Wine tour , good food , art and history the village can offer you …see more

from $105 / night

$688 / week

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Responds fast!
avg. 1 hour 25 minutes

from $105 / night

(24) Excellent 

Certificate of Excellence

43

Vacation apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Classico …see more

Certificate of Excellence

from $93 / night

$649 / week

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from $93 / night

(3) Very Good 

22

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Lovely apartment in Monticchiello (Pienza) at the entrance of the Val d'Orcia in an ancient village ' of recent construction. New apartment has satellite tv, garden with deck chairs, table and chairs on the porch. Has the most-photographed view of Tuscany and is ideal f …see more

from $62 / night

$418 - $590 / week

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Responds fast!
avg. 1 hour 48 minutes

from $62 / night

15

Vacation townhouse in Pienza

Province of Siena / Pienza

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Car not necessary
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches. It was meant to become the owner's reside …see more

from $198 / night

$1,382 / week

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from $198 / night

14

Pienza Vacation apartment rental

Province of Siena / Pienza

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about children
  • Private garden
Just a few steps from the famous Piazza Pio II, in the historical centre of Pienza, the ANCIENT COURT apartment, recently renovated in typical Tuscan style, is the ideal for couples as it has a very comfortable sofa-bed, fully equipped kitchen acumulator oven, fridge, d …see more

from $87 / night

$433 / week

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from $87 / night

7

Vacation b&b rental

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
Rigopesci Farm Bed and Breakfast & nestled in the heart of the natural park of Val d'Orcia, halfway between Siena and Florence, territory rich in history, culture, food and fine wines. We welcome you to the best of our ability to offer you a relaxing stay, to give you u …see more

from $111 / night

$614 / week

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from $111 / night

12

B&b rental in Monticchiello

Pienza / Monticchiello

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Air conditioning
The B&B is located few meters away from the entrance door to the Castle in Monticchiello. Maria Gabriella can host you in her comfortable annexe legantly furnitured. The hotel has its private bathroom with shower, TV and free internet connection. There is a private par …see more

from $121 / night

$531 / week

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from $121 / night

24

Monticchiello Vacation b&b rental

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
Inside the medieval village of Monticchiello, Maria Gabriella is happy to welcome you in its comfortable beautifully furnished annexe. The dependence is equipped with:-Separate entrance-Private bathroom with shower, Television, Air Conditioner _-Free WI-FI. From Monti …see more

from $91 / night

$482 / week

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from $91 / night

(1) Excellent 

21

Ski apartment to rent in Pienza

Province of Siena / Pienza

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ski
  • Child friendly
  • Pet friendly
Farmhouse situated in the hills, in the middle of the countryside in the Firefly Park Beautiful OASIS immersed in typical Crete Senesi. Very spacious apartment with 2 bedrooms, lounge and bathrooms .2 1 kitchen.For those who love tranquillity and a relaxing holiday.Pets …see more

from $173 / night

$803 / week

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from $173 / night

5

Pienza Vacation apartment rental

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
The building includes four brand new completely independent flats, structured on two floors; they are very new and furnished in a modern manner, equipped with all comforts like a kitchen supplied with all of the tools and household appliances, colour TV-Set, autonomous …see more

from $86 / night

$467 / week

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from $86 / night

40

Pienza Vacation farmhouse rental

Province of Siena / Pienza

9 17 7 nights min

  • 9 bedrooms
  • Sleeps 17
  • 7 nights min
  • Child friendly
  • Pet friendly
The farmhouse is situated within the ' Lucciola Bella ' Nature reserves, south west of Pienza in a small corner of the typical landscape of the crete senesi. In fact the striking feature of the nature reserve is this unusual landscape of the ' Badlands ' and ' biancane …see more

from $91 / night

$631 / week

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from $91 / night

7

B&b rental in Pienza

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The room is located on the first floor and as the flower that is inspired by that search light, enjoys a bright and beautiful views of the garden. Is cool and comfortable with a large lobby where you can enjoy breakfast, reading quietly or to add a third bed. Has a b …see more

from $93 / night

$553 / week

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from $93 / night

(1) Excellent 

12

Vacation b&b in Monticchiello

Pienza / Monticchiello

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets
Rigopesci Farm Bed and Breakfast & nestled in the heart of the natural park of Val d'Orcia, halfway between Siena and Florence, territory rich in history, culture, food and fine wines. We welcome you to the best of our ability to offer you a relaxing stay, to give you u …see more

from $111 / night

$614 / week

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from $111 / night

(1) Excellent 

15

Apartment rental in Monticchiello

Pienza / Monticchiello

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 80 mi
  • Child friendly
  • Air conditioning
The property is dated back XVIII century, has been completly restored saving the antique charme. In the centre of the village, distance by walk 3 resturants, cofee bar, grocery, bakery bank and tourist office. If you wish relax , good food good wine art and history you …see more

from $148 / night

$1,032 / week

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Responds fast!
avg. 1 hour 25 minutes

from $148 / night

9

Pienza Vacation apartment rental

Province of Siena / Pienza

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartments at Agriturismo I Casali Osteria feature a double bed, living room with kitchenette sofa bed and bathroom. Air conditioning, WI-FI, veranda, garden and use of the shared pool. Furnished in Tuscan style and well-groomed. Guests can enjoy the garden and the …see more

from $84 / night

$516 / week

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from $84 / night

24

Vacation farmhouse with swimming pool in Pienza

Province of Siena / Pienza

4 11 2 nights min

  • 4 bedrooms
  • Sleeps 11
  • 2 nights min
  • Nearest beach 95 mi
  • Swimming pool
  • Child friendly
The farmholuiday borders on a nature park in the Val d'Orcia, at Castelluccio di Pienza. Its location offers a panoramic view of two natural reserves: Pietraporciana and Lucciolabella. From the pool, nestled in an olive grove, guests enjoy a marvelous view of the entire …see more

from $479 / night

$3,071 - $3,844 / week

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from $479 / night

21

Vacation villa in Monticchiello

Pienza / Monticchiello

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
In the countryside and 5 km from Pienza, the villa on Lime Tree is a beautiful house located in the middle of the Natural and Artistic Park of Val d'Orcia. With breathtaking views and surrounded by hills, is a 10-minute drive from Pienza and Vignoni Bangna. Ideal for we …see more

from $221 / night

$1,548 / week

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from $221 / night

(1) Excellent 

11

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ski
  • Child friendly
  • Pet friendly
Located on a beautiful hillside, overlooking farm in the Valley of Val d'Orcia. An estate of 800 served as accommodation of sick, before arriving at the old hospital of Siena. In 2006 it was restored and were obtained 4 apartments. Agriturismo Chiancianello consists o …see more

from $111 / night

$430 / week

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from $111 / night

6

Vacation farmhouse in Pienza

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
Located on a beautiful hillside, overlooking farm in the Valley of Val d'Orcia. An estate of 800 served as accommodation of sick, before arriving at the old hospital of Siena. In 2006 it was restored and were obtained 4 apartments. Agriturismo Chiancianello consists o …see more

from $179 / night

$680 / week

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from $179 / night

9

Vacation guest house in Pienza

Province of Siena / Pienza

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
It is a nice and cozy apartment, as the plant that inspires, which opens directly onto the garden. Has a nice double bedroom, a bathroom with shower and a large living-kitchen fully equipped (kitchenette, fridge, point TV) characterized by a large old fireplace at gue …see more

from $105 / night

$676 / week

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from $105 / night

(2) Very Good 

20

Pienza Vacation home rental

Province of Siena / Pienza

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Just a few steps from the famous Piazza Pio II, in the historical centre of Pienza, the ANCIENT COURT apartment, recently renovated, has a double bedroom with bathroom, a bedroom with two beds, complete kitchen appliances oven, fridge and dishwasher, bathroom with showe …see more

from $123 / night

$737 - $1,253 / week

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from $123 / night

(4) Excellent 

36

Vacation apartment in Pienza

Province of Siena / Pienza

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 mi
  • Ask about children
  • Pet friendly
The apartment is on the ground floor, with private entrance, garden, small porch, living room with sofa bed, kitchen, bathroom and a double and a triple room. Its beams and its fixtures on walnut make the interior of the apartment warm, its decoration are a blend of ant …see more

from $80 / night

$559 / week

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from $80 / night

4

Vacation apartment in Pienza

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
The building includes four brand new completely independent flats, structured on two floors; they are very new and furnished in a modern manner, equipped with all comforts like a kitchen supplied with all of the tools and household appliances, colour TV-Set, autonomous …see more

from $86 / night

$467 / week

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from $86 / night

30

Vacation apartment with indoor pool in Pienza

Province of Siena / Pienza

8 15 7 nights min

  • 8 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely 18th century villa with swimming-pool in Val d'Orcia is located near Pienza, surrounded by the gently rolling hills of this magnificent countryside. This tastefully furnished villa can comfortably accommodate up to 15 people and consists of 2 large sitting r …see more

from $1,103 / night

$7,718 - $11,113 / week

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Responds fast!
avg. 2 hours 4 minutes

from $1,103 / night

(1) Excellent 

6

Apartment rental in Monticchiello

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 100 mi
  • Child friendly
The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The structure, in proximity of the principal access to the village, has been completely restructu …see more

from $156 / night

$1,007 / week

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from $156 / night

20

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $96 / night

$664 - $1,161 / week

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from $96 / night

18

Vacation apartment with shared pool in Pienza

Province of Siena / Pienza

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment with three bedrooms, three bathrooms, a large living room and a kitchen equipped with everything you need. The swimming pool and the green garden are great places to relax while enjoying a glass of wine or reading a book. Also in the surroundings you can visit …see more

from $295 / night

$2,064 / week

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Responds fast!
avg. 1 hour 5 minutes

from $295 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $79 / night

$556 - $973 / week

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from $79 / night

17

Vacation farmhouse in Monticchiello

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The Ada is in a unique position: surrounded by a large olive grove, a few hundred metres from the medieval walls of Monticchiello, is located along the panoramic road that leads to Pienza. Recently restored respecting the ancient structure, our apartment has vaulted bea …see more

from $148 / night

$921 / week

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from $148 / night

7

B&b rental in Pienza

Province of Siena / Pienza

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The room is inspired by the fresh flower: shadowy and secretive, is located on the ground floor and overlooking the garden. Is a comfortable double bedroom which on request can become two single beds. Has bathroom with shower, TV, refrigerator, and is equipped for self …see more

from $80 / night

$430 / week

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from $80 / night

14

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly
overlooking the Val D'orcia situated in a beautiful Hill, lies the AGRITURISMO CHIANCIANELLO. an old farmhouse of 800 completely restructured with comfortable and to guarantee our clients maximum tranquillity. our farmhouse is situated within the Firefly Park Beautiful …see more

from $86 / night

$492 / week

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from $86 / night

(3) Excellent 

19

Home rental in Monticchiello

Pienza / Monticchiello

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Ask about pets
  • Private garden
The House, built on an ancient structure and recently restored, is located in the heart of Monticchiello, its highest position, next to the large medieval church. Enjoys an extensive garden on the ancient walls, with a wide and incomparable views over the Woods and Vall …see more

from $154 / night

$921 / week

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from $154 / night