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Aug 29 - Aug 30
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Our top choices for Villa del Monte hotels

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 buffet setup with various food items and a seating area with wicker chairs and tables.
A pool with a view of rolling hills and distant buildings.

1. Poderi Arcangelo

Poderi Arcangelo
San Gimignano
Canada
Lisa
CA $190
CA $217 total
includes taxes & fees
Sep 2 - Sep 3
Poderi Arcangelo
A building with multiple arched windows and doors, outdoor seating areas with tables and chairs, and potted plants.
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.
A swimming pool with sun loungers and umbrellas, surrounded by a wooden fence and greenery.

2. Hotel Le Renaie

Hotel Le Renaie
San Gimignano
Germany
Sabrina
CA $215
CA $246 total
includes taxes & fees
Sep 24 - Sep 25
Hotel Le Renaie
A narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.
A rustic room with a stone ceiling, a bench, white tables, and a window with red curtains.
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.

3. Hotel Il Castello

Hotel Il Castello
Certaldo Alto
United States
Thomas
CA $188
CA $215 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Il Castello
A villa with a swimming pool, outdoor seating, and vineyard views.
A villa with a tiled roof, surrounded by lush greenery and a clear view of the countryside.
A spacious living area with a high ceiling, large windows, and a view of greenery.
A room with a bed, a chair, a suitcase, and a view of the countryside through large windows.

4. Santo Pietro Resort

Santo Pietro Resort
San Gimignano
CA $187
CA $215 total
includes taxes & fees
Sep 15 - Sep 16
Santo Pietro Resort
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 table set for dining with a view of a vineyard.
A lobby with a reception desk, a staircase, and seating areas.

5. La Cisterna

La Cisterna
San Gimignano City Centre
United States
john
CA $156
CA $181 total
includes taxes & fees
Sep 1 - Sep 2
La Cisterna
An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.
A bedroom with a bed, a desk, a chair, and a window with a view of buildings.
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.

6. Hotel Leon Bianco

Hotel Leon Bianco
San Gimignano City Centre
United States
Karen
CA $149
CA $174 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Leon Bianco
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.

7. Hotel L' Antico Pozzo San Gimignano

Hotel L' Antico Pozzo San Gimignano
San Gimignano City Centre
United States
Michael
CA $169
CA $195 total
includes taxes & fees
Aug 31 - Sep 1
Hotel L' Antico Pozzo San Gimignano
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 swimming pool with lounge chairs and umbrellas, surrounded by greenery.
A view through a window of a well-maintained garden with neatly trimmed hedges and tall trees.

8. La Collegiata

La Collegiata
San Gimignano
United States
Derek
CA $308
CA $350 total
includes taxes & fees
Sep 27 - Sep 28
La Collegiata
A stone building with an arched entrance, ivy-covered walls, and potted plants.
A cozy kitchen with a wooden bench, a dining table, and a view of a garden through arched windows.
A room with a stone floor, a sofa, a chair, and a bookshelf.
A cozy room with a glass door leading to a pool area, a wooden bench, and a table with glasses and a bottle.

9. Mormoraia

Mormoraia
San Gimignano
United States
Vivi
CA $425
CA $476 total
includes taxes & fees
Aug 31 - Sep 1
Mormoraia
A stone building with a swimming pool, outdoor seating, and trees.
A bedroom with a bed, a lamp, a chandelier, and curtains.
A view through a window of a stone wall with two towers, one with a pointed roof and the other with a rounded top.
A restaurant with a brick floor, white furniture, and a chalkboard menu.

10. Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano
CA $192
CA $220 total
includes taxes & fees
Sep 27 - Sep 28
Il Castagnolo Country B&B
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 swimming pool with lounge chairs and umbrellas, a stone building with a dome roof, and a forested hillside in the background.
A large estate with a swimming pool, surrounded by lush greenery and rolling hills.
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.

11. Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse
San Gimignano
Canada
Belinda
CA $259
CA $294 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Casolare Le Terre Rosse
An aerial view of a vineyard estate with terraced vineyards, a central building with multiple rooms, and a swimming pool.
A stone-walled building with a rustic appearance, surrounded by lush greenery and trees.
A swimming pool with lounge chairs, surrounded by greenery and a hillside.
A stone building with a stone wall and gate, a circular stone bench with a swing, and a view of the landscape.

12. Hotel Pescille by Double Hospitality

Hotel Pescille by Double Hospitality
San Gimignano
Mexico
Tania
CA $188
CA $216 total
includes taxes & fees
Sep 24 - Sep 25
Hotel Pescille by Double Hospitality
A stone building with a tiled roof, surrounded by well-maintained gardens and vineyards.
A pool area with lounge chairs and a view of the countryside.
A stone building with a rustic garden, a hanging light fixture, and a gravel path.
A landscaped garden with a fountain, stone pathways, and a view of distant hills during twilight.

13. il Casale del Cotone

il Casale del Cotone
San Gimignano
United States
Mary
CA $383
CA $429 total
includes taxes & fees
Sep 5 - Sep 6
il Casale del Cotone
A stone staircase leading up to a building with a rustic wooden roof.
An outdoor dining area with tables set for two, overlooking a pool and garden.
A restaurant with a long table displaying purple flowers, framed landscape paintings on the walls, and stone walls.
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills.

14. Casanova di Pescille

Casanova di Pescille
San Gimignano
United States
Alexander Cartaya
CA $275
CA $311 total
includes taxes & fees
Sep 14 - Sep 15
Casanova di Pescille
A pool area with lounge chairs and umbrellas, a view of a hilltop town with historic buildings.
A hotel room with a bed, a bedside table with a lamp, a small table with two glasses, and a chair.
A balcony with a table and chairs, a bucket with glasses, and a view of the landscape.
A buffet table with various food items and a sign reading 'TORRELUCENT'.

15. Cappuccina Country Resort

Cappuccina Country Resort
San Gimignano
Canada
Vince
CA $310
CA $353 total
includes taxes & fees
Sep 9 - Sep 10
Cappuccina Country Resort
A balcony with a view of the sunset, a pool, and a metal container with rocks.
A bedroom with a wooden bed, a desk with a chair, a window with curtains, and a wall-mounted lamp.
A breakfast table with tea, juice, sandwiches, and a vase of flowers.
A wooden interior with a curved ceiling and a view of a landscape through a window.

16. Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo
San Gimignano
United States
Devin Jordan
CA $238
CA $271 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Torciano Vecchio Asilo
A swimming pool with lounge chairs and umbrellas, a building with a balcony, and a stone pathway.
A table set for two with a floral centerpiece, surrounded by chairs, in a garden setting.
A vineyard estate with terraced fields, a central building with a swimming pool, and a road leading through the property.
A dining table set with plates, cutlery, and glasses, surrounded by potted plants and a view of trees.

17. Hotel Le Colline

Hotel Le Colline
San Gimignano
United States
Federico
CA $186
CA $214 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Le Colline
An outdoor dining area with tables set for two, overlooking a scenic landscape with mountains and trees.
A modern room with a large window, a bed, a desk, and a wardrobe.
A hotel entrance with arched brick architecture and a sign reading "hotel bel soggiorno".
A balcony with a table, a lamp, and a vase of flowers, overlooking a scenic landscape.

18. Hotel Bel Soggiorno

Hotel Bel Soggiorno
San Gimignano City Centre
United States
JESSICA
CA $246
CA $280 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Bel Soggiorno
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.
A restaurant with brick arches, wooden ceiling beams, and tables set for dining.
A yellow building with multiple windows and a tiled roof, surrounded by well-maintained grass and trees.

19. Boccioleto Resort&Spa

Boccioleto Resort&Spa
Montaione
United Kingdom
Jessica
CA $136
CA $160 total
includes taxes & fees
Aug 31 - Sep 1
Boccioleto Resort&Spa
A vineyard landscape with a wooden fence and red foliage in the foreground.
A two-story building with a balcony, stone walls, and potted plants.
A compact living space with a kitchenette, a dining area with a table and chairs, a sofa, and a lamp.
A table with a bottle of wine, two glasses of red wine, a plate of bruschetta, and outdoor umbrellas.

20. I Coppi

I Coppi
San Gimignano
United States
Dehai
CA $243
CA $275 total
includes taxes & fees
Sep 2 - Sep 3
I Coppi
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Top Villa del Monte Hotel Reviews

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent
"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"
Anonymous traveller 7-night trip
Posted less than an hour ago
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
Poderi Arcangelo

Poderi Arcangelo

8/10 Good
"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."
Nicholas 2-night trip
Posted 3 days ago
Poderi Arcangelo
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The resort is amazingly restored and preserved and has a wonderful family feel while remains very private and has an exclusive appeal. If it is at all possible I would highly recommend the family style dinner served on Monday night which is available to all the guests. It fascinating to interact with the people who are here for the first time or revisiting for the 30th time."
Bryan 2-night trip
Posted 3 days ago
Borgo Vescine
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

8/10 Good
"Great location easy access to Firenze"
Donnie 1-night trip
Posted 4 days ago
Fattoria il Milione Agriturismo
Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"Staff was incredibly friendly, rooms very clean and were cleaned every day, and the property is amazing! The restaurant had such great food with a nice atmosphere as well! Highly recommend staying here!"
Eric 5-night trip
Posted 5 days ago
Castello Vicchiomaggio
Villa Petriolo

Villa Petriolo

10/10 Excellent
"I like it"
Chengming 1-night trip
Posted 8 days ago
Villa Petriolo
Tenuta di Artimino Melia Collection

Tenuta di Artimino Melia Collection

10/10 Excellent
"Such a magical place. We stayed in the apartments in the village and had a wonderful stay. Everything wa"
Troy 3-night trip
Posted 2 weeks ago
Tenuta di Artimino Melia Collection
Hotel Toscana Ambassador

Hotel Toscana Ambassador

10/10 Excellent
"Room was clean, staff was helpful and easy to park."
Jennifer 3-night trip
Posted 2 months ago
Hotel Toscana Ambassador
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Great staff!"
Philip 1-night trip
Posted 2 months ago
COMO Castello Del Nero

More cheap stays in Villa del Monte

Villa Castiglione

Villa Castiglione

Via Colle Ramole 20 Impruneta FI
CA $119
CA $136 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (276 reviews)
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Antico Borgo Poggiarello

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI
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9/10 Wonderful! (20 reviews)
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Fattoria Albanese Labardi

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Borgo Tignano

Borgo Tignano

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Agriturismo Il Caggio di Sotto

Agriturismo Il Caggio di Sotto

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Agriturismo Belmonte Vacanze

Agriturismo Belmonte Vacanze

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Frequently asked questions

What is the best area to stay in Villa Del Monte?
The best area to stay in Villa Del Monte is within the historic centre, specifically around Piazza del Comune.This area is the heart of Villa Del Monte, offering a central and convenient base for exploring. You'll find charming cobbled streets, historic buildings, and a selection of local shops, restaurants, and cafes. The Piazza del Comune itself is a lovely public square, often hosting local events, and the Duomo di San Martino is a prominent landmark nearby.For couples looking for a romantic and scenic escape, staying within the historic centre is ideal. You'll be within easy walking distance of intimate trattorias, wine bars, and art galleries. The evenings are particularly pleasant for a stroll, enjoying the historic architecture and the quiet atmosphere.Travellers seeking a luxurious and secluded experience will find excellent options just outside the historic centre, located in the surrounding hills. These properties often offer stunning views of the Tuscan countryside, private pools, and extensive gardens.
When is the best time to go to Villa Del Monte?
The best time to go to Villa Del Monte is typically from late April to early June and again from early September to late October.These periods offer pleasant weather, with warm days and comfortable evenings, superb for enjoying outdoor activities and sightseeing without the intense heat of mid-summer. You'll find the countryside lush and green in spring, with blooming wildflowers, while autumn brings the spectacular colours of the harvest season and excellent opportunities for wine tasting.For couples looking for a romantic getaway, these shoulder seasons are ideal. You'll experience fewer crowds at popular attractions and restaurants, allowing for a more intimate and relaxed trip. Many local festivals celebrating food and wine also take place during these times, offering a deeper insight into Tuscan culture.Families, especially those with younger children, might prefer late spring or early autumn. The milder temperatures are more comfortable for exploring and enjoying the villa's amenities, like the swimming pool, without the risk of overheating.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Villa del Monte.
How much is the nightly rate at a Villa del Monte hotel?
Prices for hotels in Villa del Monte often vary, but you can find a great deal from CA $103 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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