Asciano Vacation Homes from ￥14,361

Rolling hills, a line of tall cypress trees, and a misty valley.

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Our top choices for Asciano vacation homes

A bedroom with a bed, a chair, a nightstand, a lamp, a decorative headboard, and a window with curtains.

1. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Monteroni d'Arbia

￥20,964 total

includes taxes & fees

Oct 14 - Oct 15

A building with a stone facade, a door, a window, and a patio area with chairs and a table.

2. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Casetta

￥17,410 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

3. Agritourism in val d'orcia

montalcino

￥60,049 total

includes taxes & fees

Oct 5 - Oct 6

A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

4. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

￥21,675 total

includes taxes & fees

Oct 6 - Oct 7

A stone building with two windows, one with green shutters, and a rose bush in the foreground.

5. Exclusive Stone Tower.

Casciano

Ryan C.

￥24,889 total

includes taxes & fees

Oct 5 - Oct 6

A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

6. Romantic farm in the Sienese hills

Trequanda, Siena

"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...

Harald B.

￥36,597 total

includes taxes & fees

Oct 5 - Oct 6

A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

7. Holday at Poggettone

Monteroni d'Arbia

￥39,440 total

includes taxes & fees

Oct 5 - Oct 6

An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

8. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

￥24,872 total

includes taxes & fees

Oct 7 - Oct 8

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

9. Double room with private bathroom in the countryside 5 minutes from Montepulciano

Toscana

￥28,781 total

includes taxes & fees

Oct 5 - Oct 6

A patio area with a gravel floor, potted plants, and a white umbrella.

10. Charming Siena Countryside Stay

Monterongriffoli

￥63,780 total

includes taxes & fees

Oct 8 - Oct 9

A brick building with a large sliding glass door, a brown door, and a small potted plant.

11. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Foiano della Chiana

￥14,361 total

includes taxes & fees

Oct 12 - Oct 13

A narrow stone alley with potted plants and benches.

12. The House of Alice, charm and relaxation

Montalcino (SI)

Robert S.

￥36,243 total

includes taxes & fees

Nov 1 - Nov 2

A stone building with a sign reading "Borgo di Mezzo".

13. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

￥25,228 total

includes taxes & fees

Oct 18 - Oct 19

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

14. Dolce Casa 2 by Tiny Away

Rigutino

￥19,064 total

includes taxes & fees

Oct 6 - Oct 7

An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

15. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

￥42,621 total

includes taxes & fees

Oct 12 - Oct 13

A rustic building with a brick facade, a small arched window, and a door.

16. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Toscana

"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."

Shanti R.

￥33,223 total

includes taxes & fees

Oct 5 - Oct 6

A balcony with a metal railing, a view of a town with terracotta-roofed buildings, and a clear sky.

17. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Poggiobrucoli

￥44,912 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor patio with a wooden table and chairs, surrounded by a wooden pergola, and a view of greenery.

18. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

￥28,070 total

includes taxes & fees

Oct 31 - Nov 1

A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

19. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Toscana

￥31,267 total

includes taxes & fees

Oct 7 - Oct 8

A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

20. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Monte San Savino

"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...

Anonymous traveler

￥36,953 total

includes taxes & fees

Oct 6 - Oct 7

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Top Asciano Hotel Reviews

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

Castello di Leonina Relais

10/10 Excellent

"We loved staying here. The hotel was full of history and in a beautiful location. The views overlooking the Tuscan hills were spectacular. We loved the quiet location and enjoyed walks on and near the property. Renting a car is a must and was perfect to take day trips to the beautiful historic Tuscan hill towns. The included breakfast was a beautiful spread with so much to choose from. We got quite spoiled between the delicious breakfasts and the dinners at the property restaurant. The staff was very helpful and friendly. Grazie mille! :) This hotel is a must and we will definitely be back when we visit Tuscany again."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"

Find out more about Asciano

Asciano Vacation Homes information

Number of reviews	115
Accommodation	1620 Vacation Homes
Lowest Price	￥14,361
Highest Price	￥63,780

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Asciano vacation homes

1. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

2. Peaceful corner with garden between Chianti and Crete, very close to Old Town

3. Agritourism in val d'orcia

4. "Il Focolare" Superior Apartment in Monticchiello

5. Exclusive Stone Tower.

6. Romantic farm in the Sienese hills

7. Holday at Poggettone

8. Podere Belsogno-camera Lavanda

9. Double room with private bathroom in the countryside 5 minutes from Montepulciano

10. Charming Siena Countryside Stay

11. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

12. The House of Alice, charm and relaxation

13. The Gelda house, relax with a view

14. Dolce Casa 2 by Tiny Away

15. Suite Gioconda - Podere Casa Rossa in Pienza

16. Cozy Tuscan-style apartment Suitable for families. Pets allowed

17. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

18. Holiday Home 'La Casina All'angolo'

19. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

20. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Find vacation rentals that suit your style

Top Asciano Hotel Reviews

Four Points by Sheraton Siena

Monastero di Cortona Hotel & Spa

Fattoria di Vegi

Nuovo Etruria Resort

Castello di Leonina Relais

Castello di Spaltenna- Small Luxury Hotels of the World

Castiglion del Bosco, A Rosewood Hotel

Hotel Athena

La Certosa di Pontignano

Find out more about Asciano

Asciano Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Asciano

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Asciano vacation homes

1. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

2. Peaceful corner with garden between Chianti and Crete, very close to Old Town

3. Agritourism in val d'orcia

4. "Il Focolare" Superior Apartment in Monticchiello

5. Exclusive Stone Tower.

6. Romantic farm in the Sienese hills

7. Holday at Poggettone

8. Podere Belsogno-camera Lavanda

9. Double room with private bathroom in the countryside 5 minutes from Montepulciano

10. Charming Siena Countryside Stay

11. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

12. The House of Alice, charm and relaxation

13. The Gelda house, relax with a view

14. Dolce Casa 2 by Tiny Away

15. Suite Gioconda - Podere Casa Rossa in Pienza

16. Cozy Tuscan-style apartment Suitable for families. Pets allowed

17. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

18. Holiday Home 'La Casina All'angolo'

19. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

20. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Find vacation rentals that suit your style

Top Asciano Hotel Reviews

Four Points by Sheraton Siena

Find out more about Asciano

Asciano Vacation Homes information

Explore a world of travel with Expedia