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Search results; Over 1,000 homes in Montalcino

Top guest favorite
This Montalcino farmstay is a converted chapel surrounded by vineyards you can tour
2 bedrooms, 2 beds, 1 private bath
Oct 21 – 26
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4.96 out of 5 average rating, 79 reviews
Superhost
Original frescoes greet you in this restored Montalcino apartment in Val d’Orcia
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 3 baths
Sep 25 – 30
Top guest favorite
Look out over valley vineyards from this restored Montalcino palazzo
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 5 baths
Aug 21 – 26
Top guest favorite
This Montalcino townhouse gives you a private garden, jacuzzi, and wood stove
5.0 out of 5 average rating, 153 reviews, 1 bedroom, 1 bed, 1 bath
Aug 18 – 23
Top guest favorite
From this three-level Montalcino house, you’ll take in countryside views on your terrace
4.95 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Top guest favorite
This tranquil Montalcino vacation home gives you alfresco dining and outdoor seating
5.0 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bath
Oct 4 – 9
This renovated Montalcino apartment gives you views over Val d’Orcia
2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Top guest favorite
This hilltop apartment in a 13th-century monastery gives you all of Montepulciano’s views
4.97 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 14 – 19
This renovated Montalcino farmhouse gives you an olive grove and hill views
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 19 – 24
Top guest favorite
Olive groves and panoramic views surround you at this 17th-century Pienza villa
4.99 out of 5 average rating, 110 reviews, 2 bedrooms, 3 beds, 1 bath
Nov 11 – 16
Top guest favorite
A 1000-year-old tower in San Quirico d’Orcia where you’ll overlook Val d’Orcia
5.0 out of 5 average rating, 114 reviews, 1 bedroom, 1 bed, 1 bath
Aug 24 – 29
Guest favorite
Private room
Wake to Tuscan countryside views from this sunlit Montalcino room’s private terrace
4.95 out of 5 average rating, 61 reviews, 1 king bed, 1 bath
Aug 25 – 30
Guest favorite
This renovated condo puts you right on Montalcino’s central square
4.75 out of 5 average rating, 76 reviews, 1 bedroom, 2 beds, 1 bath
Sep 23 – 28
Guest favorite
This hilltop Montalcino farmstay gives you 360° views over Val d’Orcia vineyards
4.98 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
This Monticchiello apartment gives you countryside views, a fireplace, and a piano
4.97 out of 5 average rating, 186 reviews, 3 bedrooms, 4 beds, 2 baths
Nov 17 – 22
Top guest favorite
A restored 16th-century barn where you’ll wake among olive groves in Pienza
5.0 out of 5 average rating, 158 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 30 – Nov 4
Top guest favorite
From the pool in an olive grove, you’ll take in all of Val d’Orcia at this ancient tower house
5.0 out of 5 average rating, 34 reviews, 4 bedrooms, 8 beds, 4 baths
Aug 31 – Sep 5
Top guest favorite
This Trequanda apartment gives you panoramic hill views and a private garden
5.0 out of 5 average rating, 24 reviews, 1 bedroom, 1 bed, 1 bath
Aug 24 – 29
Top guest favorite
Wake to Val d’Orcia views from this vineyard-surrounded San Quirico farmstay
4.98 out of 5 average rating, 115 reviews, 5 bedrooms, 5 beds, 5.5 baths
Aug 30 – Sep 4