Top 10 Hotels Near Rocca of Montestaffoli in San Gimignano for 2026

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Our top choices for Rocca of Montestaffoli hotels

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 rustic dining area with a stone fireplace, wooden beams, and a long table set for dining.

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.

1. Agriturismo Il Segreto di Pietrafitta

2.7 km from Rocca of Montestaffoli

Michelle

P23,292

P25,976 total

includes taxes & fees

Oct 9 - Oct 10

An outdoor café with tables and chairs, a whiteboard, and a door with a sign.

A cozy interior with a dining area, striped chairs, a rug, and a painting on the wall.

A warmly lit street with a building featuring arched doorways and a sign above the entrance.

A restaurant with stone walls, framed artwork, and tables set for dining.

2. Locanda Il Pino

San Gimignano City Centre, 0.2 km from Rocca of Montestaffoli

Thomas

P5,747

P6,677 total

includes taxes & fees

Oct 3 - Oct 4

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

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

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

A room with a window, a radiator, a chair, a table with a lamp and a book, and a bottle.

3. Tenuta Guardastelle

1.6 km from Rocca of Montestaffoli

Sarah

P15,442

P17,341 total

includes taxes & fees

Oct 10 - Oct 11

A bedroom with a bed, bedside table, lamp, and a desk with a chair.

A modern walk-in closet with mirrored doors, built-in shelves, and a central mirror.

A small, modern room with a desk, chair, and a framed picture of lemons on the wall.

A walk-in closet with hanging space and shelves, featuring a mirror and a blue object on the upper shelf.

4. Duccio Nacci Rooms - guest house

San Gimignano City Centre, 0.3 km from Rocca of Montestaffoli

Tessa

P8,360

P9,551 total

includes taxes & fees

Oct 10 - Oct 11

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 well-lit outdoor area with a stone building, tall trees, and a pathway leading to the entrance.

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

5. Tenuta Sovestro - Agriturismo e Winery

1.7 km from Rocca of Montestaffoli

J MANUEL

P12,256

P13,836 total

includes taxes & fees

Oct 22 - Oct 23

A swimming pool with lounge chairs and a view of a hill with buildings.

An aerial view of a vineyard with rows of grapevines, a large building with a swimming pool, and a distant hilltop town.

A cozy dining area with a wooden table and chairs, a sofa, and a fireplace.

A view from a window overlooking a rural landscape with rolling hills and vineyards.

6. Agriturismo Il Casolare di Bucciano

2.1 km from Rocca of Montestaffoli

"The views and quality of this agriturismo is simply outstanding. Peaceful and surreal, the view of San Gimigano are amazing. We had a wonderful time. Breakfast options could have been more varied for vegetarians and the staff member who greeted us on arrival could have been a little more welcoming! All other members of staff were outstanding. Did their best to accommodate us, including cooking special egg free dishes! Gratzie!"

Satnam

P7,663

P8,784 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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

A man and a woman in a restaurant with a stone wall and a wooden table.

7. Hotel Sovestro

1.7 km from Rocca of Montestaffoli

Manuel

P9,616

P11,004 total

includes taxes & fees

Oct 25 - Oct 26

A stone building with a wooden door, a stone wall, and a wooden balcony.

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

A restaurant with a long table displaying purple flowers, framed landscape paintings on the walls, and stone walls.

A traditional stone building with a tiled roof, surrounded by tall evergreen trees and a field of lavender.

8. Casanova di Pescille

2 km from Rocca of Montestaffoli

Alexander Cartaya

P11,214

P12,692 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

9. Hotel Leon Bianco

San Gimignano City Centre, 0.2 km from Rocca of Montestaffoli

CINTHIA ELAINE DE

P7,346

P8,506 total

includes taxes & fees

Oct 22 - Oct 23

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 hotel room with a large bed, a desk with two chairs, a ceiling fan, and a TV mounted on the wall.

10. Hotel Bel Soggiorno

San Gimignano City Centre, 0.3 km from Rocca of Montestaffoli

Sheri

P12,256

P13,907 total

includes taxes & fees

Oct 1 - Oct 2

A view from a window overlooking a pool, greenery, and a distant building.

An outdoor patio with wicker furniture, a stone table, and a potted plant.

A bedroom with a large window overlooking a garden and a distant view of a hill with buildings.

A pool area with a stone building, two umbrellas, and a statue.

11. B&B Ponte a Nappo

1.2 km from Rocca of Montestaffoli

Madison

P9,634

P10,953 total

includes taxes & fees

Oct 18 - Oct 19

A stone building with a tiled roof, surrounded by well-maintained gardens and vineyards.

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.

A pool area with lounge chairs and a view of the countryside.

12. il Casale del Cotone

2.3 km from Rocca of Montestaffoli

Mary

P12,554

P14,165 total

includes taxes & fees

Oct 23 - Oct 24

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

An outdoor dining area with stone walls, potted plants, and a table set for two.

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

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

13. Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre, 0.2 km from Rocca of Montestaffoli

Michael

P7,934

P9,153 total

includes taxes & fees

Oct 8 - Oct 9

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 lobby with a reception desk, a staircase, and seating areas.

14. La Cisterna

San Gimignano City Centre, 0.2 km from Rocca of Montestaffoli

john

P6,585

P7,669 total

includes taxes & fees

Oct 28 - Oct 29

An open wooden door leading to an outdoor patio with a table and chairs.

A kitchen with a sink, stove, and cabinets, a dining area with a bench and chairs, and a chandelier.

A man in a suit standing next to a chair in a room with a chandelier, a potted plant, and a painting on the wall.

A dining area with wooden tables, chairs, a chandelier, and a kitchen in the background.

15. Palazzo al Torrione 2

San Gimignano City Centre, 0.3 km from Rocca of Montestaffoli

Angela

P6,661

P9,455 total

includes taxes & fees

Oct 2 - Oct 3

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.

16. Hotel Le Colline

1.4 km from Rocca of Montestaffoli

Federico

P6,099

P7,135 total

includes taxes & fees

Oct 25 - Oct 26

A view from a window overlooking a rural landscape with fields and a distant mountain range.

A kitchen with a large island, a dining area with a table and chairs, and a view through arched windows.

A cozy room with a stone fireplace, a round table with chairs, and a colorful striped sofa.

A traditional room with a large bed, a wooden desk, and a stone wall.

17. B&B Palazzo Tortoli

San Gimignano City Centre, 0.2 km from Rocca of Montestaffoli

Harold

P8,640

P9,859 total

includes taxes & fees

Oct 18 - Oct 19

A woman seated on a striped sofa with a cushion, under a canopy with string lights, surrounded by greenery and a brick wall.

A fountain surrounded by a stone wall, with trees and shrubs in the background.

A modern hotel lobby with red seating, a kitchen area, and a staircase leading to an upper floor.

A modern living room with red chairs, a coffee table, and a staircase with a unique design.

18. Hotel Da Graziano

0.7 km from Rocca of Montestaffoli

KARYL

P5,117

P6,055 total

includes taxes & fees

Oct 18 - Oct 19

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 stone building with a tiled roof, outdoor seating area with lounge chairs, and a gravel path.

19. Il Castagnolo Country B&B

2.8 km from Rocca of Montestaffoli

Allan

P7,353

P8,444 total

includes taxes & fees

Oct 4 - Oct 5

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

A view through a window of a well-maintained garden with neatly trimmed hedges and tall trees.

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.

20. La Collegiata

1.5 km from Rocca of Montestaffoli

Derek

P11,509

P13,157 total

includes taxes & fees

Oct 30 - Oct 31

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Top Rocca of Montestaffoli Hotel Reviews

Hotel L' Antico Pozzo San Gimignano

10/10 Excellent

"Very good location, clean rooms and bathrooms."

Relais Santa Chiara Hotel by Double Hospitality

8/10 Good

"This was a good one night stay and a perfect walk to town."

Hotel Sovestro

10/10 Excellent

"without a doubt, this one of the nicest places that my wife and i have stayed, a hidden gem in the beautiful hills of Tuscany! the location is spotless and offers several pools and quiet areas to relax. the staff was amazing, Laura and Michael tended to everything making the stay remarkable. we had to catch a super early flight and Laura worked tirelessly to find us a private taxi to get to the airport by 5:00 am. the food was beyond explanation; best spaghetti that we have ever had, breakfast was a spread of the best meats and cheeses, etc. and home reminders including eggs and bread items. highly recommend this wonderful location if you are traveling to Tuscany, we will be returning in the future."

La Cisterna

10/10 Excellent

"Such an amazing location, we chose the more expensive room with a view across the country side and it was definitely worth it. Easy to find in the middle of the main square"

Residenza d'Epoca Palazzo Buonaccorsi

10/10 Excellent

"It was a unique experience staying in an old medieval building with a beautiful view of the towers of San Gimignano. The bathroom was a little small, but the room itself was quite spacious. I do wish the bedding had been a little cleaner. The host welcomed us warmly, and the town was absolutely beautiful. It is definitely a place I would love to visit again."

I Coppi

10/10 Excellent

"Picture post card view from everwhere. Breakfast was euthentic traditional fare with a few western additions. Relaxed walk to town. The view was the real Tuscany."

Locanda Il Pino

10/10 Excellent

"Walkable to the main plaza and bus stops, the property has its own restaurant. Breakfast was awesome. We enjoyed our stay and will definitely stay there again when we go back to San Gimigagno."

Materia Rooms San Gimignano

10/10 Excellent

"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."

Hotel Le Colline

10/10 Excellent

"Our stay was very pleasant. The staff was fantastic. Awesome breakfast. Room was spacious and clean. Easy access to city center. The only “down” side was that the AC wasn’t very effective but we expected that with older accommodations and extreme August heat. I would definitely stay there again."

Other attractions near Rocca of Montestaffoli

A historic stone building with tall towers and a bell tower.

Piazza delle Erbe

9.4/10 (21 reviews)

Watch the world go by and admire San Gimignano’s medieval architecture from the comfort of a café terrace at this central square.

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A historic stone church with two prominent towers, surrounded by ancient ruins and a dense forest.

San Gimignano Communal Palace

9.4/10 (150 reviews)

You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

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Fortress of Montestaffoli

8.6/10 (4 reviews)

You can learn about the history of San Gimignano with a trip to Fortress of Montestaffoli. Discover the area's beautiful countryside and wineries.

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Vernaccia di San Gimignano Wine Museum

9.2/10 (15 reviews)

You can browse the exhibits at Vernaccia di San Gimignano Wine Museum, a museum with a storied past, during your travels to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

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Ornithological Museum

You can study the exhibits at Ornithological Museum, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside and wineries.

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Piazza Luigi Pecori

Learn about the local history of San Gimignano when you take a trip to Piazza Luigi Pecori. Discover the countryside in this walkable area.

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Museum of Sacred Art

You can study the exhibits at Museum of Sacred Art, a museum with a storied past, during your travels to San Gimignano. Discover the area's beautiful countryside and wineries.

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Podesta's Palace

9.6/10 (13 reviews)

You can find out about the history of San Gimignano with a visit to Podesta's Palace. Discover the area's beautiful countryside and wineries.

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Frequently asked questions

What's the area like around Rocca of Montestaffoli?

Rocca of Montestaffoli is located in San Gimignano. Travelers like this historic area for its countryside. If you're looking for a convenient place to stay, check out the 160 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Rocca of Montestaffoli?

Adjacent to Rocca of Montestaffoli, Hotel Leon Bianco is one of the top choices for your stay based on our traveler data, and this hotel offers a fitness center and a bar. Other good choices close by include La Cisterna and Hotel L' Antico Pozzo San Gimignano.

How many hotels will I be able to find near Rocca of Montestaffoli?

Expedia has 160 hotels and other accommodations within a mile from Rocca of Montestaffoli.

If I need to cancel the hotel reservation for my stay near Rocca of Montestaffoli, will I receive a refund?

Yes, you'll find most hotel room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of booking. Add your dates and click on "Search", then you can use the "fully refundable" filter to view the top deals on offer near Rocca of Montestaffoli.

What can I see and do near Rocca of Montestaffoli?

You'll want to browse the collections at Vernaccia di San Gimignano Wine Museum, San Gimignano Communal Palace, and Medieval Criminal and Torture Museum. Sights like Casa e Torre Campatelli, Podesta's Palace, and Torre Grossa are must-sees while exploring the area. Create some family memories at The SottoVico Garden and Ra-Ma snc.

Hotels near Rocca of Montestaffoli

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Rocca of Montestaffoli hotels

1. Agriturismo Il Segreto di Pietrafitta

2. Locanda Il Pino

3. Tenuta Guardastelle

4. Duccio Nacci Rooms - guest house

5. Tenuta Sovestro - Agriturismo e Winery

6. Agriturismo Il Casolare di Bucciano

7. Hotel Sovestro

8. Casanova di Pescille

9. Hotel Leon Bianco

10. Hotel Bel Soggiorno

11. B&B Ponte a Nappo

12. il Casale del Cotone

13. Hotel L' Antico Pozzo San Gimignano

14. La Cisterna

15. Palazzo al Torrione 2

16. Hotel Le Colline

17. B&B Palazzo Tortoli

18. Hotel Da Graziano

19. Il Castagnolo Country B&B

20. La Collegiata

Top Rocca of Montestaffoli Hotel Reviews

Hotel L' Antico Pozzo San Gimignano

Relais Santa Chiara Hotel by Double Hospitality

Hotel Sovestro

La Cisterna

Residenza d'Epoca Palazzo Buonaccorsi

I Coppi

Locanda Il Pino

Materia Rooms San Gimignano

Hotel Le Colline

Other attractions near Rocca of Montestaffoli

Piazza delle Erbe

San Gimignano Communal Palace

Fortress of Montestaffoli

Vernaccia di San Gimignano Wine Museum

Ornithological Museum

Piazza Luigi Pecori

Museum of Sacred Art

Podesta's Palace

Frequently asked questions