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Macciano Vacation Rentals

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Our top choices for Macciano vacation rentals

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 CA $207
CA $230 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Dolciano

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 CA $166
CA $185 total
includes taxes & fees
Nov 1 - Nov 2
La Piccola Locanda

3. 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 CA $144
CA $197 total
includes taxes & fees
Nov 1 - Nov 2
Affitacamere Maria Gabriella

4. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 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 CA $206
CA $232 total
includes taxes & fees
Nov 26 - Nov 27
La Locanda di San Francesco

5. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is CA $160
CA $182 total
includes taxes & fees
Oct 31 - Nov 1
montorio

6. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (168 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is CA $191
CA $220 total
includes taxes & fees
Nov 5 - Nov 6
Hotel San Gregorio

7. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (120 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 CA $207
CA $234 total
includes taxes & fees
Nov 7 - Nov 8
Meublé Il Riccio

8. Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
The price is CA $132
CA $161 total
includes taxes & fees
Nov 2 - Nov 3
Boutique Apartment Natura

9. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (49 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is CA $238
CA $268 total
includes taxes & fees
Oct 31 - Nov 1
Delcorto Suites

10. 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 CA $144
CA $165 total
includes taxes & fees
Nov 30 - Dec 1
Bed & Breakfast Vicolo dell'Oste

11. 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 CA $106
CA $119 total
includes taxes & fees
Nov 5 - Nov 6
FonteLiving

12. 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 CA $91
CA $105 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais

13. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is CA $133
CA $162 total
includes taxes & fees
Nov 2 - Nov 3
Boutique Apartment Eleganza

14. 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 CA $123
CA $142 total
includes taxes & fees
Nov 5 - Nov 6
Residenza Fabroni

15. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is CA $295
CA $426 total
includes taxes & fees
Nov 5 - Nov 6
Eagle House

16. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is CA $114
CA $148 total
includes taxes & fees
Nov 22 - Nov 23
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

17. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is CA $157
CA $179 total
includes taxes & fees
Nov 15 - Nov 16
Casale dell'Assiolo

18. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (104 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 CA $250
CA $282 total
includes taxes & fees
Nov 24 - Nov 25
Casanova - Panoramic Rooms and Suites

19. 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 CA $316
CA $354 total
includes taxes & fees
Nov 30 - Dec 1
Il Tosco

20. 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 CA $624
CA $693 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
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

Find out more about Macciano

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Macciano. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Macciano?

Yes, you can find vacation rentals close to the most popular points of interest in Macciano, or you can go with a more secluded option if you'd like a relaxing place to stay. Macciano is known for its wineries and restaurants.

What are some of the best vacation home rentals that Macciano has to offer?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental near Macciano is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 larger area.

What’s a vacation rental in Macciano like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Macciano. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.