Montespertoli Piazza Machiavelli Hotels: 2026 Limited-Time Hotel Deals @Expedia

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Our top choices for Piazza Machiavelli hotels

An outdoor patio area with seating and a stone fireplace.

A garden with a wooden staircase leading to a house.

A restaurant table set with plates, glasses, and a basket of bread.

A two-story house with a tiled roof, surrounded by trees and a dirt path.

1. Le Mandrie di Ripalta

1.3 km from Piazza Machiavelli

Alaa

HK$1,650

HK$1,852 total

includes taxes & fees

13 Sept - 14 Sept

A table with three wine glasses and a bottle, set against a backdrop of a vineyard and rolling hills.

A clear blue pool with lounge chairs and a stone wall.

A restaurant with multiple tables set for dining, featuring a rustic wooden ceiling and large windows.

A traditional villa with a garden, a patio with outdoor furniture, and a white tent.

2. Podere dell'Anselmo

5 km from Piazza Machiavelli

Sabrina

HK$881

HK$1,005 total

includes taxes & fees

2 Oct - 3 Oct

A rural property with a swimming pool, a small house, and surrounding greenery.

A cozy kitchen with wooden beams, a dining table with chairs, a TV, and a stove.

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

An arched doorway leading to a garden with terracotta pots and red flowers.

3. Tenuta Moriano

3.4 km from Piazza Machiavelli

Cara

HK$558

HK$1,242 total

includes taxes & fees

12 Oct - 13 Oct

A pool area with a sunset view, surrounded by trees and a distant mountain range.

A dining table set with plates, a candle, and a vase with flowers.

A sunlit outdoor seating area with a pergola and lounge chairs.

A rural landscape with a small shed, trees, and a field.

4. Le Mammole

16.8 km from Piazza Machiavelli

Yuriy

HK$786

HK$864 total

includes taxes & fees

24 Sept - 25 Sept

A swimming pool with a wooden deck, lounge chairs, and umbrellas in a landscaped garden.

A modern living room with a sofa, a lamp, and a view through an archway to a kitchen area.

A table set for a meal with various cheeses, meats, and a bottle of wine, outdoors with a house in the background.

A dining area with a chandelier, tables, chairs, and a buffet table with food and drinks.

5. Borgo Elissa

12.2 km from Piazza Machiavelli

Danit

HK$1,011

HK$1,158 total

includes taxes & fees

20 Sept - 21 Sept

A narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.

A living room with a sofa, armchairs, a coffee table, and a painting on the wall.

A staircase with a wooden handrail and black balusters, leading to an upper floor.

A rustic room with exposed brick walls, a piano, and a dining table set with white tableware.

6. Hotel Il Castello

10.9 km from Piazza Machiavelli

Thomas

HK$1,062

HK$1,214 total

includes taxes & fees

14 Sept - 15 Sept

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

A swimming pool with clear water, surrounded by lounge chairs and trees.

A stone building with a tower, a glass structure, and outdoor seating.

A kitchen area with a marble countertop, a stone wall, and a sign reading "Cooking Class".

7. Salvadonica - Borgo del Chianti

11.4 km from Piazza Machiavelli

Jonathan

HK$1,693

HK$1,899 total

includes taxes & fees

11 Oct - 12 Oct

An outdoor patio area with brick walls, stone flooring, and tables with red tablecloths.

A cozy outdoor seating area with wicker furniture, a large umbrella, and stone flooring.

A building with a tiled roof and a window, surrounded by greenery and a field of yellow flowers.

A small building with a tiled roof, a covered outdoor seating area with chairs and umbrellas, and a gravel courtyard with potted plants.

8. Country Hotel Borgo Sant'Ippolito

9 km from Piazza Machiavelli

Evauna

HK$1,202

HK$1,368 total

includes taxes & fees

21 Sept - 22 Sept

A large villa with a swimming pool, surrounded by lush greenery and hills.

A dining area with a brick fireplace, a stone wall, and a wooden table set for four.

A patio with stone flooring and white chairs, overlooking a town with rolling hills and greenery.

A stone building with a terrace and a view of the countryside.

9. Agriturismo Cantagallo

13 km from Piazza Machiavelli

Charlene

HK$707

HK$796 total

includes taxes & fees

18 Sept - 19 Sept

A large building with a swimming pool, surrounded by greenery and outdoor lighting.

A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

A courtyard with a lawn, seating area, and a weeping willow tree.

A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.

10. LHP Certaldo Resort

11.6 km from Piazza Machiavelli

Arash

HK$1,102

HK$1,266 total

includes taxes & fees

12 Oct - 13 Oct

A modern interior with a cozy grey sofa, a small round table, and a wall with a large botanical mural.

A covered outdoor seating area with tables and chairs, surrounded by potted plants and trees.

A room with a wooden table, two white chairs, a black table, and a TV mounted on the wall.

A modern living room with a black chair, a white wardrobe, and a flat-screen TV on the wall.

11. HOMY BnB

13.5 km from Piazza Machiavelli

Ginger

HK$744

HK$1,028 total

includes taxes & fees

13 Sept - 14 Sept

An outdoor dining area with wicker chairs and tables, white tablecloths, and umbrellas, overlooking a scenic landscape.

A spacious living room with a large window offering a view of the countryside. There are two armchairs, a sofa, and a coffee table with a vase of flowers.

A dining area with stone walls, wooden beams, and round tables set for a meal.

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

12. Villa Le Calvane

3.5 km from Piazza Machiavelli

Darryl

HK$4,784

HK$5,327 total

includes taxes & fees

3 Oct - 4 Oct

A rural villa with a courtyard, surrounded by trees and fields.

A spacious living room with a fireplace, a large marble column, and a view through an open door.

A poolside area with a table, chairs, a bench, and an umbrella.

A stone building with a garden, including a pergola with purple flowers.

13. Il Poggio B&B

6.8 km from Piazza Machiavelli

Vitaliy

HK$825

HK$944 total

includes taxes & fees

20 Sept - 21 Sept

A restaurant with wooden tables set for dining, red cushioned seating, and a warm ambiance.

A vineyard with rows of grapevines, a few buildings, and rolling hills in the background.

A bedroom with a bed, a small cabinet, and a stone wall.

A bar area with a large ELEKTRA grill, shelves of liquor bottles, and a menu board.

14. Locanda Il Gallo

19 km from Piazza Machiavelli

Santina

HK$908

HK$1,026 total

includes taxes & fees

20 Sept - 21 Sept

A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

An interior space with a wooden bench, a potted plant, and two framed pictures on the wall.

A swimming pool surrounded by stone walls and lush greenery, with a view of distant hills.

A rustic stone building with ivy-covered walls, outdoor seating, and gravel ground.

15. I Parigi Corbinelli

15.7 km from Piazza Machiavelli

Jacqui

HK$837

HK$1,030 total

includes taxes & fees

27 Sept - 28 Sept

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

A view from a covered outdoor area with a paved floor, leading to a garden with various plants and a distant landscape.

An outdoor patio area with tables and chairs, a reception desk, and potted plants.

A stone building with a rustic exterior, surrounded by lush greenery and outdoor seating areas.

16. Hotel Villa San Giorgio

17.4 km from Piazza Machiavelli

Arik

HK$737

HK$847 total

includes taxes & fees

29 Sept - 30 Sept

A dining area with a table set for four, overlooking a scenic landscape.

A large estate with multiple buildings, a swimming pool, and extensive vineyard fields.

A pool with a view of rolling hills and distant buildings.

A bedroom with a bed, a desk, a TV, and a window with curtains.

17. Poderi Arcangelo

13.7 km from Piazza Machiavelli

Lisa

HK$1,103

HK$1,259 total

includes taxes & fees

28 Sept - 29 Sept

A building entrance with a glass door, steps leading up to it, and potted plants on either side.

A modern kitchen with stainless steel appliances, a built-in oven, and a microwave. There is a small dining area with a white table and chairs.

A rooftop patio with a table and chairs, surrounded by potted plants and a pergola.

A modern hotel room with a large bed, a bedside table, a mirror, and a wardrobe.

18. appartamenti la piazzetta

15.3 km from Piazza Machiavelli

Courtney

HK$738

HK$1,166 total

includes taxes & fees

16 Sept - 17 Sept

A couple sitting at an outdoor table with a view of the countryside.

A breakfast tray with bread, eggs, and a flower by a window.

A rectangular swimming pool with lounge chairs and umbrellas, surrounded by tall trees and a clear sky.

A cozy room with a large window, a tray of breakfast items, and a bed with a blanket.

19. Fonte de' Medici

14.5 km from Piazza Machiavelli

Stephen

HK$2,158

HK$2,411 total

includes taxes & fees

21 Sept - 22 Sept

A dining area with a table set for two, featuring a view of greenery through a window.

A table with a bottle of Chianti wine, two wine glasses, a book, a magazine, and a bouquet of lilacs.

A bedroom with a large bed, a smaller bed, and a window with curtains.

A sign reading "CAMERE" against a clear blue sky.

20. La Locanda di Pietracupa

18.2 km from Piazza Machiavelli

Isabell

HK$1,375

HK$1,549 total

includes taxes & fees

1 Oct - 2 Oct

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Top Piazza Machiavelli Hotel Reviews

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

10/10 Excellent

"We couldn’t have asked for a nicer and more perfect accommodation for our family of 19. Nicola was superb to communicate with and he was there to see to our every need. The property and grounds were beautiful and exceptionally clean and had everything we could ask for. It also was an easy distance for exploring Florence and other areas in Tuscany. We loved the pool for relaxing during the hot days and the children enjoyed the playground We highly recommend staying here and hope to come back ourselves in the future. Thank you Nicola!"

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

10/10 Excellent

"A fabulous villa for a large group. Easily accommodating 14 for our family. Definitely need a vehicle as getting around to shops, trains or access to Florence is not easy.The pool and grounds are fantastic. Surrounded by olive groves. Host and his family could not have been nicer or more responsive.The air conditioning in each room was a blessing in 35’ heat.Highly recommend!!"

Castello di Montegufoni

10/10 Excellent

"It’s quite an idyllic place and setting. We stayed in the older part of the castle. Expect character !"

Villa il Poggiale - Dimora Storica

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ I honestly don’t think I could write a review that does this place justice. From the moment we arrived, we were completely blown away. This beautiful historic house is surrounded by absolutely stunning scenery, a gorgeous pool, vineyards stretching for miles, and so much history and character. The house itself is incredible, but what really made our stay special was how warm, caring, and helpful the staff were. When we arrived, we were given a full tour of the property, and the whole experience genuinely felt like being welcomed into someone’s home. There’s something so special about this place. The history, the beauty, the atmosphere, and the incredible hospitality all come together perfectly. And the food was AMAZING. The pasta portions are on the smaller side (our ravioli was 6 pieces), but every bite was absolutely delicious and completely worth it. And the Florentine steak was MASSIVE, easily the best steak I’ve ever had! We had such an amazing time and truly didn’t want to leave. We will 1000% be back. ❤️"

VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.

10/10 Excellent

"Villa Belsole exceeds the listing. We were a big party of 18 made up of five families who have holidayed together several times previously and this property met our expectations 100%. We did make use of the option to have additional beds which provided further flexibility for the sleeping arrangements and meant parents could have separate rooms from the children in all cases. Communication with Enzo and Christina was perfect and although there was a small misunderstanding during check-in regarding the additional cost of electricity and water for the week this was quickly resolved. We took advantage of using the local cook on-site for one evening which was an excellent choice and we were able to adjust the menu to suit our party's tastes and dietary needs - the food was wonderful and plentiful. Indoor and outdoor dining tables, which could seat us all, were made good use of and the pool gave a welcome break from the high temperatures in August and has a view which never failed to look anything but spectacular. Aircon operates throughout the property in all the rooms and makes for a very comfortable nights sleep. The villa is perfectly positioned for day trips to Florence, Siena and Pisa with the local town of Certaldo having well stocked Supermarkets. A perfect holiday which both the parents and children thoroughly enjoyed - highly recommended. Thank you."

Locanda del podestà: 17th century mansion in Chianti

10/10 Excellent

"The villa is stunning. The small town is amazing."

House with character in typical medieval borgo on the Chianti Classico hills

10/10 Excellent

"Es gibt nur Gutes über dieses Ferienhaus zu sagen. Der Besitzer war vor Ort als wir ankamen, wies uns ein und gab uns sogar Tips für Restaurants in der Nähe. Die Lage ist perfekt für Trips nach San Gimignano, Siena und Florenz. Das "kleine mittelalterliche Dorf" ist genau das, klein, freundliche Nachbarn, unglaublich romantisch. Das Haus selbst ist riesig und authentisch eingerichtet. Die Küche ist gut bestückt, der Besitzer hatte Gewürze, Kaffee, Pasta, Obst etc bereitgestellt. Wirklich ein super Service und ein toller Aufenthalt."

Chianti family villa, 5 bedrooms, infinity pool, A/C, BBQ, 360° view

10/10 Excellent

"Our stay was just lovely. Paola and Pietro were very responsive when we had a power issue. The house is gorgeous, the pool delightful, and I will never forget the views!!"

Villa Le Calvane

10/10 Excellent

"Great staff! Beautiful property. The food is amazing. The pool is beautiful. The view is unreal. We live it. We will be back. Thanks"

Other attractions near Piazza Machiavelli

Museo Amedeo Bassi

You can spend time exploring the galleries in Museo Amedeo Bassi during your travels in Montespertoli. Discover the countryside in this relaxing area or seek out the cycling trails.

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Castello Sonnino

5.4/10 (3 reviews)

You can enjoy a tasting or tour at Castello Sonnino during your travels to Montespertoli. Visit the churches and wineries in this walkable area.

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Montespertoli City Hall

10.0/10 (2 reviews)

Montespertoli City Hall is just one of the places to see in Montespertoli, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside in this walkable area or enjoy its local tours.

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Il Fiaschetto

Enjoy an outing to Il Fiaschetto during your stay in Montespertoli. Discover the beautiful countryside in this walkable area or enjoy its local tours.

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Piazza del Popolo

You can find out about the history of Montespertoli when you stop by Piazza del Popolo. Discover the beautiful countryside in this walkable area or enjoy its local tours.

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Vine and Wine Museum

10.0/10 (1 review)

You can spend an afternoon studying the exhibits at Vine and Wine Museum during your travels in Montespertoli. Visit the stunning cathedral and wineries in this walkable area.

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Pieve di San Pietro in Mercato

You can learn about the history of Montespertoli with a trip to Pieve di San Pietro in Mercato. Discover the countryside in this relaxing area or seek out the cycling trails.

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Tenuta Barbadoro

You can enjoy a tasting or tour at Tenuta Barbadoro during your travels to Montespertoli. Discover the beautiful countryside and wineries in this relaxing area.

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Frequently asked questions

What's the area like around Piazza Machiavelli?

Piazza Machiavelli is located in a welcoming area of Montespertoli known for its selection of wineries and sightseeing. If you're looking for a convenient place to stay, take a look at the 21 hotels and other accommodation options you'll find within a mile.

Where is the best place to stay near Piazza Machiavelli?

Castello di Montegufoni is one of the top choices for your stay based on our traveller data, and this residence offers a restaurant and an outdoor pool. It's located 2 mi (3.2 km) from Piazza Machiavelli. Other good options within 5 miles include Villa Le Calvane and Podere dell'Anselmo.

How many hotels should I expect to find close to Piazza Machiavelli?

Expedia has 21 hotels and other accommodation options within a mile from Piazza Machiavelli.

If I need to cancel the hotel reservation for my stay near Piazza Machiavelli, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review top deals close to Piazza Machiavelli.

What can I see and do near Piazza Machiavelli?

While you're exploring, swing by Montegufoni Castle, Castle of Poppiano and Castle of Oliveto to learn a bit about the area. Stopping by Castello Sonnino, Tenuta Barbadoro or Tenuta Maiano is a fun way to see all the area has to offer. Museo Amedeo Bassi, Montespertoli City Hall and Il Fiaschetto are a few additional nearby sights.

Montespertoli Piazza Machiavelli Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Piazza Machiavelli hotels

1. Le Mandrie di Ripalta

2. Podere dell'Anselmo

3. Tenuta Moriano

4. Le Mammole

5. Borgo Elissa

6. Hotel Il Castello

7. Salvadonica - Borgo del Chianti

8. Country Hotel Borgo Sant'Ippolito

9. Agriturismo Cantagallo

10. LHP Certaldo Resort

11. HOMY BnB

12. Villa Le Calvane

13. Il Poggio B&B

14. Locanda Il Gallo

15. I Parigi Corbinelli

16. Hotel Villa San Giorgio

17. Poderi Arcangelo

18. appartamenti la piazzetta

19. Fonte de' Medici

20. La Locanda di Pietracupa

Top Piazza Machiavelli Hotel Reviews

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Castello di Montegufoni

Villa il Poggiale - Dimora Storica

VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.

Locanda del podestà: 17th century mansion in Chianti

House with character in typical medieval borgo on the Chianti Classico hills

Chianti family villa, 5 bedrooms, infinity pool, A/C, BBQ, 360° view

Villa Le Calvane

Other attractions near Piazza Machiavelli

Museo Amedeo Bassi

Castello Sonnino

Montespertoli City Hall

Il Fiaschetto

Piazza del Popolo

Vine and Wine Museum

Pieve di San Pietro in Mercato

Tenuta Barbadoro

Frequently asked questions