50 Best Vacation Rentals in Monticchiello - Holiday Lettings - Cabins

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52 Vacation rentals

(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 $142 / night

$993 / week

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Responds fast!
avg. 2 hours 14 minutes

from $142 / night

(2) Excellent 

24

Vacation apartment with shared pool in Monticchiello

Pienza / Monticchiello

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis. The owners have carefully furnished the prop …see more

from $210 / night

$1466 - $2287 / week

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from $210 / night

(4) Excellent 

21

Tower rental in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask about children
  • Private garden
In Val d'Orcia, Monticchiello di Pienza is a small medieval town, surrounded by walls and protected by four towers; one of these is ' Charles ' Tower, which stands at the highest point of the village and has a panoramic view across the Valley. Sunsets and beautiful wil …see more

from $176 / night

$939 / week

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from $176 / 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 $235 / night

$1408 / week

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from $235 / night

(1) Excellent 

12

Monticchiello Vacation b&b rental

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 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 $106 / night

$587 / week

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Responds fast!
avg. 3 hours 27 minutes

from $106 / 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 $86 / night

$458 / week

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Responds fast!
avg. 2 hours 44 minutes

from $86 / night

(2) Excellent 

22

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • 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 $59 / night

$399 - $514 / week

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Responds fast!
avg. 3 hours 42 minutes

from $59 / night

(6) Excellent 

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 $100 / night

$657 / week

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Responds fast!
avg. 2 hours 14 minutes

from $100 / 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 $106 / night

$587 / week

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Responds fast!
avg. 3 hours 27 minutes

from $106 / night

32

Monticchiello Vacation townhouse rental

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
House with private pool,reserved to one booking so to guarantee privacy is in the pool, in home and in the garden.With views over Monticchiello, Pienza and Montepulciano. Also from here you can see the famous "Monticchiello" curves that were the backdrop to many intern …see more

from $212 / night

$1408 - $1642 / week

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from $212 / 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 $115 / night

$505 / week

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Responds fast!
avg. 2 hours 44 minutes

from $115 / night

(23) 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 $88 / night

$434 - $1058 / week

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from $88 / night

(2) Very Good 

24

Vacation apartment rental

Pienza / Monticchiello

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Private garden
CAMPO ALLA PIANA è un podere in campagna ma a soli 500 metri dal borgo di Monticchiello di Pienza. Mettiamo a disposizione degli ospiti 3 camere spaziose, luminose e ben arredate; anche i bagni sono eleganti , spaziosi e con ampie finestre. Dalle camere si può ammirar …see more

from $235 / night

$1408 / week

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from $235 / night

(3) Excellent 

19

Home rental in Monticchiello

Pienza / Monticchiello

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 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 $147 / night

$880 / week

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from $147 / 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 $106 / night

$587 / week

Book View

Responds fast!
avg. 3 hours 27 minutes

from $106 / night

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 $149 / night

$962 / week

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from $149 / night

(3) Excellent 

24

Vacation b&b in Monticchiello

Pienza / Monticchiello

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
A small village, the landscapes of the Val d'Orcia, an ancient historical residence dating back to the 13th century. These are just some of the features of ' La Casa di Adelina, a bed and breakfast in & montichiello, small village near Pienza. Monticchiello is little mo …see more

from $445 / night

$2944 / week

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from $445 / night

9

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
Questo mini-appartamento offre un'unica ed incredibile vista della valle che circonda Pienza sia dalla finestra di camera che dal soggiorno. E' possibile ammirare per chilometri, fin dove arriva lo sguardo, uno dei più bei panorami della campagna toscana. L'appar …see more

from $129 / night

$903 / week

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from $129 / night

10

Monticchiello Vacation townhouse rental

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
The hospitality and refinement of the Bed and Breakfast La Casa di Adelina continues in the quiet apartment situated in the center of Monticchiello. The nock will leave you speechless! This capability provides our guests to stay in a context of value, architectural st …see more

Pricing unknown

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Pricing unknown

30

Vacation apartment rental

Pienza / Monticchiello

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly
The Farmhouse Fonte Senesi is a house of 230 square meters located in the beautiful Val d'Orcia, the valley of the Crete Senesi in southern Tuscany. The independent appartamentio is furnished with antique furniture, air conditioning, in the floor is a handmade terracott …see more

from $528 / night

$3401 - $4222 / week

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from $528 / 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 $212 / night

$1478 / week

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from $212 / night

(1) Very Good 

24

Vacation b&b in Monticchiello

Pienza / Monticchiello

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
The B&B is located few meters away from the entrance door to the Castle in Monticchiello. Maria Gabriella can host you in her 4 comfortable rooms elegantly furnitured. Each room has its private bathroom with shower, TV and free internet connection. There is a private p …see more

from $106 / night

$704 - $2921 / week

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Responds fast!
avg. 2 hours 44 minutes

from $106 / night

18

B&b rental in Monticchiello

Pienza / Monticchiello

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Air conditioning
Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione. L'Antica Locanda …see more

from $100 / night

$645 / week

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from $100 / night

11

Home rental in Monticchiello

Pienza / Monticchiello

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
The property is dated back 11TH century and still now has the same structure, like a tower on 3 levels. Completly restored has every comfort: air condition, sat Tv and private garden. The house is located in the main square of a tiny village included in Unesco's heritag …see more

from $141 / night

$845 / week

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Responds fast!
avg. 2 hours 14 minutes

from $141 / 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 $141 / night

$880 / week

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from $141 / night

10

Vacation townhouse in Monticchiello

Pienza / Monticchiello

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
As one of the first farm that once began the Agritourism activity, we are today certainly more than satisfied that other farmers followed our example with such enthusiasm. It is not easy to put in words which feelings to holiday in our farmhouse will awake in somebody, …see more

Pricing unknown

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Pricing unknown

(2) Very Good 

49

Monticchiello Vacation villa accommodation

Pienza / Monticchiello

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Between Pienza and Montepulciano fascinating Villa of three hundred. The real estate complex of 800 square meters. ca composed of the main house, two outbuildings, a loft, a studio, and various local wineries; They are connected by a beautiful courtyard covered with a v …see more

from $1055 / night

$6685 - $8163 / week

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from $1055 / night

(1) Excellent 

12

Monticchiello Vacation farmhouse rental

Pienza / Monticchiello

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden


The Podere Ada, a typical rural structure of the early ' 900, is in a unique position: surrounded by a large olive grove, a few hundred metres from the medieval walls of Monticchiello, is situated along the panoramic road that leads to Pienza. 
The farm consists of a …see more

from $235 / night

$1173 / week

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from $235 / night

31

Vacation villa in Monticchiello

Pienza / Monticchiello

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
  • Child friendly
  • Private garden
This 800 sq.mts.Villa has been recently restored combining traditional materials as old cotto for the floors and oak beams for the ceilings with vintage furniture and contemporary art works. The insulated large walls and the ventilated roof keep the house naturally coo …see more

from $939 / night

$7037 / week

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from $939 / night

6

Monticchiello Vacation b&b rental

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione. L'Antica Locanda è ub …see more

from $110 / night

$710 / week

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from $110 / night

6

Vacation b&b in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione. L'Antica Locanda è ub …see more

from $110 / night

$710 / week

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from $110 / night

9

Monticchiello Vacation apartment rental

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
Questo grazioso mini-appartamento si affaccia sullo storico Corso di Pienza. La camera è arredata con mobili '800 di querce massiccia. Oltre al letto matrimoniale, il sofà della camera può essere trasformato in terzo letto. La cucina è provvista di forno, fornel …see more

from $129 / night

$903 / week

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from $129 / night

19

Vacation home rental

Pienza / Monticchiello

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Private garden
Just South of Siena, The Val d’Orcia is UNESCO World Heritage. Its enchanting towns and villages like Montalcino and Pienza are surrounded by a sea of vines and olives whose slopes intermittently give way to deep forest of pines, chestnuts and oaks, cool and refreshing. …see more

from $243 / night

$2111 / week

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from $243 / night

6

Monticchiello Vacation b&b rental

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione. L'Antica Locanda …see more

from $110 / night

$710 / week

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from $110 / night

6

Vacation b&b in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
La spaziosa camera si affaccia su un cortile privato nella parte antica di Pienza. È arredata con mobili antichi della tradizione toscana, compreso uno splendido cassettone del XVIII sec. Il letto matrimoniale in ferro battuto ha una testata dipinta a motivi flor …see more

from $110 / night

$710 / week

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from $110 / night

14

Vacation home in Monticchiello

Pienza / Monticchiello

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 70 mi
  • Child friendly
  • Air conditioning
The property is located in a beatifull medioeval village between Pienza and Montepulciano in UNESCO'S Heritage The house is dates back XI century , you will feel the history in the meantime you will have every confort. The building is on 3 levels like a little tower …see more

from $141 / night

$986 / week

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Responds fast!
avg. 2 hours 14 minutes

from $141 / night

37

Monticchiello Vacation apartment rental

Pienza / Monticchiello

6 Min stay varies

  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
On a large estate surrounded by olive groves and flower fields, this Italian villa is just the place if you and your family are looking for beauty and tranquility. Whether its sunrises in the morning, sunsets in the evening, or midday gazing, you’ll have views that will …see more

from $337 / night

$1906 - $3117 / week

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from $337 / night

54

Monticchiello Vacation home rental

Pienza / Monticchiello

14 7 nights min

  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
On a large estate surrounded by olive groves and flower fields, this Italian villa is just the place if you and your group are looking for beauty and tranquility. Whether its sunrises in the morning, sunsets in the evening, or midday gazing, you’ll have views that will …see more

from $832 / night

$4566 - $7822 / week

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from $832 / night

(1) Excellent 

29

Vacation farmhouse in Monticchiello

Pienza / Monticchiello

8 7 nights min

  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
When you look out the windows of this restored farmhouse in Tuscany, you’ll be gazing out on the landscape that has inspired everyone from Renaissance painters to modern-day UNESCO – the green, rolling hills of the Val d’Orcia. With views from the windows of the modern …see more

from $552 / night

$3864 - $7616 / week

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from $552 / night

(1) Excellent 

22

Monticchiello Vacation villa rental

Pienza / Monticchiello

8 7 nights min

  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Situated in a prominent position overlooking the Val d’Orcia, this villa for rent in Tuscany offers incredible views and is in a peaceful and natural setting. It’s within walking distance of Monticchiello, which is home to many shops and restaurants as well as a castle. …see more

from $600 / night

$4200 - $6138 / week

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from $600 / night