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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Macciano holiday rentals

A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

1. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is 3.840.600 ₫
4.282.656 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Borgo Dolciano
A bakery display with various pastries and desserts.

2. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is 3.080.388 ₫
3.446.423 ₫ total
includes taxes & fees
24 Oct - 25 Oct
La Piccola Locanda
A crowded restaurant with brick walls and multiple tables and chairs.

3. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (151 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is 4.191.674 ₫
4.726.834 ₫ total
includes taxes & fees
15 Nov - 16 Nov
La Locanda di San Francesco
A patio area with outdoor seating, potted plants, and a view of the landscape.

4. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is 2.811.496 ₫
3.814.697 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Affitacamere Maria Gabriella
An interior courtyard with stone columns, arches, and a mosaic.

5. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is 4.132.228 ₫
4.661.442 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Meublé Il Riccio
Exterior

6. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is 2.918.368 ₫
3.326.081 ₫ total
includes taxes & fees
25 Oct - 26 Oct
montorio
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

7. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (166 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is 3.736.694 ₫
4.284.468 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A terrace with a table set for breakfast, overlooking a scenic landscape.

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (48 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is 4.444.775 ₫
5.005.245 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Delcorto Suites
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

9. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (138 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is 5.978.879 ₫
6.692.759 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Il Tosco
An arched doorway leading to a building with a wooden door and a staircase.

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (115 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
The price is 2.338.290 ₫
2.688.111 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Residenza Fabroni
A historic building with a tower, a courtyard, and a well-lit entrance.

11. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is 1.921.783 ₫
2.200.955 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Abbadia Sicille Relais
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

12. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is 2.728.576 ₫
3.117.426 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

13. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (21 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is 2.111.588 ₫
2.380.743 ₫ total
includes taxes & fees
29 Oct - 30 Oct
FonteLiving
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

14. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is 11.599.237 ₫
12.875.153 ₫ total
includes taxes & fees
2 Nov - 3 Nov
L'Olmo
A poolside area with two glasses of water, candles, and a stone pathway.

15. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (103 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is 4.639.695 ₫
5.219.656 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Casanova - Panoramic Rooms and Suites
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

16. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (6 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is 2.091.574 ₫
2.416.723 ₫ total
includes taxes & fees
2 Nov - 3 Nov
PienzaLettings Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

17. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is 2.277.598 ₫
2.621.350 ₫ total
includes taxes & fees
2 Nov - 3 Nov
TuscanyLettings Studio&Room
A stone building with a wooden door, a staircase, and a small window with a metal grill.

18. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is 2.936.056 ₫
3.345.654 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Casa Gioia - Casa Olivieri
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

19. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is 3.321.442 ₫
3.769.462 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A stone archway leading to a building entrance with a wooden door.

20. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
5.6 out of 10, (5 reviews)
"Na"
United States
Abel
The price is 1.714.136 ₫
2.001.542 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Bellarmino Boutique Apartments
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Macciano Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."
Charles 6-night trip
Posted 12 hours ago
Castello di Velona Resort Thermal SPA & Winery

Frequently asked questions

Can I find holiday rentals in Macciano?

Yes, there are holiday rentals close to the most popular sights in Macciano, or you can select a more secluded option if you're looking for a relaxing stay. Macciano is known for its wineries and restaurants.

What’s there to see and do in Macciano?

While exploring the area, visit family-friendly sights like Centro Servizi Turistici Citta della Pieve, or get outside and enjoy nature at Terme Sant'Elena. Terme di Chianciano and Piazza Italia are a couple of places you'll find in the wider area.

What’s a holiday rental in Macciano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Macciano. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.