Hotels in Villa del Monte

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Where to stay in Villa del Monte?

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

An aerial view of a vineyard estate with terraced fields, a swimming pool, and a curved building with a tiled roof.

A restaurant interior with wooden furniture, wine bottles, and glasses on the table.

A table set outdoors with wine glasses and cutlery, surrounded by greenery and trees.

1. Hotel Sovestro

San Gimignano

$133

$153 total

includes taxes & fees

Nov 2 - Nov 3

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

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

A dining area with tables and chairs, a kitchen in the background, and a patterned wall.

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

2. LHP Certaldo Resort

Certaldo

$112

$129 total

includes taxes & fees

Oct 29 - Oct 30

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

A rustic interior with a brick staircase, a wooden door, and a stone wall.

A courtyard with a hanging planter, potted plants, and a brick wall.

A pool with a view of a vineyard and hills.

3. Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

$81

$94 total

includes taxes & fees

Oct 30 - Oct 31

A swimming pool with lounge chairs and umbrellas, a building with a balcony, and a stone pathway.

A vineyard estate with terraced fields, a central building with a swimming pool, and a road leading through the property.

A bedroom with a bed, a nightstand, a vase with dried plants, and a wall mural of a landscape.

A table set for two with a floral centerpiece, surrounded by chairs, in a garden setting.

4. Hotel Le Colline

San Gimignano

$97

$113 total

includes taxes & fees

Oct 25 - Oct 26

A table set for dining with a view of a hilltop town.

A stone-walled room with a hot tub, wooden beams, and a view of the outdoors.

A stone-walled room with a large bathtub, wooden beams, and a view through a window.

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

5. La Collegiata

San Gimignano

$159

$183 total

includes taxes & fees

Oct 30 - Oct 31

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

A bedroom with a bed, a desk with a chair, a fireplace, and a window with a view of buildings.

A breakfast setting with croissants, fruit salad, and a cup of coffee on a table.

A cozy bar area with brick arches, white leather chairs, and a bar counter stocked with bottles.

6. Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

$101

$118 total

includes taxes & fees

Nov 4 - Nov 5

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

A buffet setup with various food items and beverages, wooden crates, and a stone wall background.

A rustic stone building with a wooden ceiling and a view of a vineyard.

A gravel driveway leading to a stone building with a garden and tall trees.

7. Tenuta Sovestro - Agriturismo e Winery

San Gimignano

$153

$174 total

includes taxes & fees

Nov 9 - Nov 10

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

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.

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

8. Hotel Il Castello

Certaldo Alto

$131

$150 total

includes taxes & fees

Oct 20 - Oct 21

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

A modern hotel room with a bed, a desk, a chair, and a TV.

A modern bar area with purple seating, a laptop on a shelf, and a wine display.

A modern living room with leather furniture, a glass coffee table, and a white brick wall.

9. Park Hotel Chianti

Tavarnelle Val di Pesa

$66

$79 total

includes taxes & fees

Nov 17 - Nov 18

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

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.

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

10. Hotel Villa San Giorgio

Poggibonsi

$60

$66 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

A buffet setup with various food items and a seating area with wicker chairs and tables.

11. Poderi Arcangelo

San Gimignano

$108

$125 total

includes taxes & fees

Nov 8 - Nov 9

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

A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.

A yellow building with stone pillars, multiple windows, and a statue in the garden.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

12. Villa San Lucchese

Poggibonsi

$113

$124 total

includes taxes & fees

Nov 4 - Nov 5

A building with multiple arched windows and doors, outdoor seating areas with tables and chairs, and potted plants.

A courtyard with a stone pathway surrounded by potted hydrangeas in various colors.

A spacious living room with a fireplace, wicker furniture, and a view of the garden through open doors.

A building with a courtyard featuring potted plants and flowers.

13. Hotel Le Renaie

San Gimignano

$101

$117 total

includes taxes & fees

Oct 26 - Oct 27

A dining table with a view of a pool and landscaped garden.

A hotel with a swimming pool, outdoor seating, and a view of the surrounding town.

A room with a fireplace, a table with a tray of food, and two lamps on either side of the fireplace.

A garden area with potted plants, a red scooter, and a white umbrella.

14. Relais Santa Chiara Hotel by Double Hospitality

San Gimignano

$102

$120 total

includes taxes & fees

Oct 20 - Oct 21

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

A restaurant with brick arches, wooden ceiling beams, and tables set for dining.

A table set for dining outdoors with a view of the garden and trees.

A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.

15. Boccioleto Resort&Spa - Place of Charme

Montaione

$71

$85 total

includes taxes & fees

Nov 4 - Nov 5

A stone staircase leading to a gated entrance, surrounded by lush greenery and a well-maintained lawn.

A rustic stone building with a small patio area featuring a terracotta pot with flowers, a metal chair, and a small table.

A stone building with a tiled roof, a gravel path, and potted plants.

A buffet table with various food items and glass containers, set in an outdoor area with a wooden ceiling and a view of trees.

16. Tenuta Decimo

San Gimignano

$50

$60 total

includes taxes & fees

Oct 25 - Oct 26

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

A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view.

A historic square with stone buildings, a central fountain, and a tower.

A table set for dining with a view of a vineyard.

17. La Cisterna

San Gimignano City Centre

$99

$116 total

includes taxes & fees

Nov 5 - Nov 6

A stone building with an arched entrance, ivy-covered walls, and potted plants.

A cozy room with a glass door leading to a pool area, a wooden bench, and a table with glasses and a bottle.

A room with a stone floor, a sofa, a chair, and a bookshelf.

A kitchen with a herringbone tile floor, a breakfast bar with fruit and bread, and a view of a garden through a glass door.

18. Mormoraia

San Gimignano

$259

$291 total

includes taxes & fees

Nov 1 - Nov 2

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

A reception desk with a curved design, a framed painting above it, a potted plant to the right, and a window with curtains.

A gym with treadmills, weight machines, and free weights.

A desk with a book titled 'The Ancestors' Tale' by Richard Dawkins, a magazine, a pen, and a pair of glasses.

19. Hotel Leon Bianco

San Gimignano City Centre

$109

$126 total

includes taxes & fees

Nov 1 - Nov 2

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

A spa area with wooden benches and a glass partition, a modern bathroom with a large sink, and a corridor leading to another room.

A hotel room with a large bed, a desk, and a chair, a view of a city through the window, and a ceiling light.

A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

20. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

$116

$132 total

includes taxes & fees

Nov 8 - Nov 9

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

LHP Certaldo Resort

Certaldo

10/10 Exceptional

RAMONA

Hotel Le Colline

San Gimignano

10/10 Exceptional

The facilities are well maintained. The beds are comfortable and the setting in the Tuscan countryside is wonderful. Very peaceful and serine. The pool is clean and refreshing. The location is perfect, being just far enough away from the daily crowds in the town of San Gimignano, but close enough to visit before 10 AM and after dusk. The included daily breakfast was a perfect start to our day! Lots of fresh fruit, juice, yogurts, granolas, breads and cold cuts. And, of course, the espresso...

Ron

Hotel Villa San Giorgio

Poggibonsi

10/10 Exceptional

Arik

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

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

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

Poderi Arcangelo

San Gimignano

10/10 Exceptional

Cathy

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

A gated entrance with tall cypress trees, a paved path leading to a building with a yellow facade, and a mountain in the background.

A bedroom with a bed, a desk, and a chair. There is a window with curtains, a painting on the wall, and a view of greenery outside.

An outdoor dining area with multiple tables and chairs, surrounded by buildings with balconies and a staircase.

A swimming pool with a stone building in the background, surrounded by trees and outdoor seating.

Hotel Casolare Le Terre Rosse

San Gimignano

10/10 Exceptional

charles

Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

10/10 Exceptional

The accomodations were awesome! I would highly recommend this hotel. She does not take credit cards and it is difficult to find. However, she will send you an e-mail prior to arrival with all these details as well as how to find the hotel. You can park out front while checking in and then you drive about 100 meters to a free parking lot .... very convenient. The City is wodnerful are easily walkable!

Anonymous traveler

Hotel Le Renaie

San Gimignano

10/10 Exceptional

marley

A glass table with two wine glasses and a lantern on a patio with potted plants and a view of the city skyline at dusk.

A two-story building with a yellow facade, arched windows, and a garden with various plants and flowers.

A swimming pool with a view of a historic city on a hill.

A spacious living room with a high ceiling, stone walls, a wooden floor, a sofa, a coffee table, and a dog lying on the floor.

Agriturismo Il Segreto di Pietrafitta

San Gimignano

10/10 Exceptional

Vicki

Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

10/10 Exceptional

Dorothy

La Collegiata

San Gimignano

10/10 Exceptional

Damon

Tenuta Decimo

San Gimignano

10/10 Exceptional

Laura

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Exceptional

Fred

A table with a bottle of wine, two glasses, and a plate of food on a balcony overlooking a historic cityscape.

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

A breakfast buffet with various food items, a pitcher, cups, and a view of the outdoors.

A reception sign for a taste and shop, surrounded by greenery and a gravel path leading to buildings.

Tenuta Guardastelle

San Gimignano

10/10 Exceptional

Paige

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.