Hotels in Villa del Monte

Q: What accommodations do travelers like in Villa del Monte?

Guests like Castelfalfi , Poderi Arcangelo and Hotel Casolare Le Terre Rosse .

Where to?

Dates

November 2026

December 2026

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Where to stay in Villa del Monte?

A pool area with lounge chairs and umbrellas, surrounded by greenery and buildings.

1. Hotel Sovestro

San Gimignano

$152 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

2. Villa San Lucchese

Poggibonsi

$105 total

includes taxes & fees

Nov 29 - Nov 30

A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.

3. Boccioleto Resort&Spa - Place of Charme

Montaione

$65 total

includes taxes & fees

Nov 3 - Nov 4

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

4. Hotel Villa San Giorgio

Poggibonsi

$66 total

includes taxes & fees

Nov 8 - Nov 9

A vineyard with rows of grapevines, a swimming pool, and a building with a red roof.

5. Hotel Le Colline

San Gimignano

$114 total

includes taxes & fees

Nov 2 - Nov 3

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

6. Hotel Il Castello

Certaldo Alto

$149 total

includes taxes & fees

Nov 4 - Nov 5

A stone building with a swimming pool, outdoor seating, and trees.

7. Il Castagnolo Country B&B

San Gimignano

$107 total

includes taxes & fees

Nov 13 - Nov 14

A historic street with a hotel entrance featuring an arched doorway and potted plants.

8. Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

$114 total

includes taxes & fees

Nov 4 - Nov 5

A stone building with a swimming pool, outdoor seating, and a waterfall feature.

9. Tenuta Sovestro - Agriturismo e Winery

San Gimignano

$173 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor courtyard with stone walls, arched doorways, and potted plants.

10. Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

$89 total

includes taxes & fees

Nov 2 - Nov 3

A poolside area with lounge chairs and umbrellas, surrounded by a landscaped garden with red flowers.

11. Poderi Arcangelo

San Gimignano

$124 total

includes taxes & fees

Nov 26 - Nov 27

A hotel entrance with a glass facade, a brown awning, and a garden with pink flowers.

12. Hotel La Vecchia Cartiera

Colle di Val d'Elsa

$84 total

includes taxes & fees

Nov 22 - Nov 23

A person sitting by a swimming pool with a stone building in the background.

13. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

$119 total

includes taxes & fees

Nov 29 - Nov 30

A modern bedroom with a wooden floor, a bed with a headboard, a window with curtains, and a shower area with a towel rack.

14. Park Hotel Chianti

Tavarnelle Val di Pesa

$77 total

includes taxes & fees

Nov 22 - Nov 23

A person sitting in a hot tub with a waterfall feature in the background.

15. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

$131 total

includes taxes & fees

Nov 8 - Nov 9

A rock garden with various succulents and plants.

16. Hotel Toscana Ambassador

Poggibonsi

$74 total

includes taxes & fees

Nov 22 - Nov 23

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

17. Villa Sabolini

Colle di Val d'Elsa

$91 total

includes taxes & fees

Nov 30 - Dec 1

A pool area with lounge chairs and umbrellas, a view of a hilltop town with historic buildings.

18. Cappuccina Country Resort

San Gimignano

$228 total

includes taxes & fees

Nov 15 - Nov 16

A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.

19. La Cisterna

San Gimignano City Centre

$104 total

includes taxes & fees

Nov 14 - Nov 15

An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.

20. Hotel Leon Bianco

San Gimignano City Centre

$119 total

includes taxes & fees

Nov 2 - Nov 3

View all properties

Go beyond your typical stay in Villa del Monte

Check out reviews of Villa del Monte hotels guests love

Hotel Sovestro

San Gimignano

10/10 Exceptional

Mikhail

Villa San Lucchese

Poggibonsi

10/10 Exceptional

Beautiful property with large rooms, parlors, great staff, great restaurant, etc. We arrived late and the kitchen was closed, but they made one call and re-opened it for us and served an amazing meal with late night enthusiasm on a beautiful deck. The rooms were large, nice baths and very comfortable beds. We wanted to stay another night to relax by the pool and enjoy the wonderful grounds, but they were booked so we had to move on as this was a last minute booking. Great breakfast in the...

Anonymous traveler

Hotel Il Castello

Certaldo Alto

10/10 Exceptional

Have you ever wanted to stay in a medieval walled city? This family owned and operated hotel is where you should stay! It's comfortable, quiet and the food at the restaurant is to die for. We loved everything about it! Each evening, we would relax in the courtyard while enjoying the view. Then we would order a delicious dinner. It's hard to pick our favorite dish, but I would have to say the poached egg with a crunchy shell on a cheese sauce with shaved truffle was unique and amazing.

JoAnna

Tenuta Sovestro - Agriturismo e Winery

San Gimignano

10/10 Exceptional

We loved our stay! The winery is beautiful, and you can see the vineyards and cypress trees from your room. Beautiful views! The stay includes the best breakfast buffet in all of Italy with fresh food and coffee. The dinner restaurant is great for a cozy meal. The shuttle into town is very convenient if you don't want to walk uphill. The walk back to tenuto sovestro from town is gorgeous and enjoyable (all downhill.) We enjoyed the brief wine tasting and stories of what makes this winery...

Amanda

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

10/10 Exceptional

We cannot recommend this hotel enough. The price was so worth it. The resort has a delicious restaurant, comfortable and luxurious accommodations, a lovely bar, relaxing pool area, and the most amazing Tuscan hills view. We can attest that the romantic sunset they promote is spot on. There is a quaint downtown a 10 minutes walk away as well. It was conveniently located to Florence and many other Tuscan locations. It was amazing to get an authentic Tuscan experience.

Alyssa

Boccioleto Resort&Spa - Place of Charme

Montaione

10/10 Exceptional

We stayed at Boccioleto Resort & Spa for five nights with our two kids and absolutely loved it. The hotel is stunning, surrounded by greenery, with spacious rooms and a pool overlooking breathtaking views. The staff is impeccable—always warm, attentive, and genuinely committed to making every guest feel special. You can really sense the team’s effort to create an unforgettable experience. Breakfast was delicious, and if we had more time, we would have gladly extended our stay.

Gadi

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Exceptional

Fred

Hotel Le Colline

San Gimignano

10/10 Exceptional

Federico

Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

10/10 Exceptional

Dorothy

Hotel Villa San Giorgio

Poggibonsi

10/10 Exceptional

Arik

A balcony with a view of the sunset, a pool, and a metal container with rocks.

Hotel Torciano Vecchio Asilo

San Gimignano

10/10 Exceptional

Necola

Il Castagnolo Country B&B

San Gimignano

10/10 Exceptional

Anonymous traveler

Hotel Leon Bianco

San Gimignano City Centre

10/10 Exceptional

We loved this place! Getting here was a bit tricky, as the map we were given in the welcome email was of bad quality, so it didn't take us to the correct place right away, but we figured it out, very minor. I'm sure you can ask for a better quality map. When we arrived to check in, we were greeted by Lisa, who was oh so very helpful! She showed us where laundry was, asked all questions we had about WIFI and other hotel things, recommended us 3 terrific places to eat dinner on each of our 3...

Todd

Frequently Asked Questions

What accommodations do travelers like in Villa del Monte?

Guests like Castelfalfi, Poderi Arcangelo and Hotel Casolare Le Terre Rosse.

Can I book a refundable accommodation in Villa del Monte?

If you need the flexibility to change your plans to Villa del Monte, most properties offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in Villa del Monte be like during my trip?

August and July are typically the warmest months in Villa del Monte when the average temp is 73°F. January and February are the coldest months when the average temperature is 44°F. November and October are the months with the most rain.

Why should I book my Villa del Monte accommodation with Hotels.com?

There are lots of reasons to book your Villa del Monte trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.