Hotels in Il Castagno

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Where to stay in Il Castagno?

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 bedroom with a bed, a bench, a dresser, and a window.

1. Poderi Arcangelo

San Gimignano

$108

$124 total

includes taxes & fees

Nov 13 - Nov 14

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

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

2. LHP Certaldo Resort

Certaldo

$128

$148 total

includes taxes & fees

Oct 30 - Oct 31

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 two-story building with a tiled roof, a central entrance, and a small balcony.

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

3. Boccioleto Resort&Spa - Place of Charme

Montaione

$62

$75 total

includes taxes & fees

Oct 27 - Oct 28

An outdoor patio with a table and chairs, a stone building with a balcony, and a sign that reads "Cucco".

A buffet setup with various food items and a view of the outdoors through large windows.

A hotel room with a bathtub, a bed, a desk, and a window with curtains.

A hallway with a large painting of a rural scene, a cushioned bench, and a view of the outdoors through a glass door.

4. Hotel le Macine

Montaione

$84

$97 total

includes taxes & fees

Oct 26 - Oct 27

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

A stone building with a tiled roof, a small attached structure, and a well-maintained garden with flowers and shrubs.

A cozy living room with a fireplace, a green sofa, a wooden coffee table, and a stone fireplace surround.

A pool area with lounge chairs and umbrellas, surrounded by stone walls and greenery, with a view of distant hills.

5. Il Defizio

Gambassi Terme

$124

$140 total

includes taxes & fees

Oct 23 - Oct 24

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

A dining table set with plates, cutlery, and glasses, surrounded by potted plants and a view of trees.

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.

6. Hotel Le Colline

San Gimignano

$97

$113 total

includes taxes & fees

Oct 25 - Oct 26

A courtyard with outdoor seating, potted plants, and a building with a tiled roof.

A restaurant with tables and chairs, a kitchen area, and a large window offering a view of trees.

A residential area with houses, a parking lot, and a street lamp.

A hotel room with a large bed, a bedside table with a lamp, a small desk, and a chair.

7. Hotel Foresteria Volterra

Volterra

$92

$107 total

includes taxes & fees

Oct 23 - Oct 24

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

A balcony with a table and chairs, a bucket with glasses, and a view of the landscape.

An aerial view of a residential property with multiple buildings, a swimming pool, and a well-maintained garden.

A buffet table with various food items and a sign reading 'TORRELUCENT'.

8. Cappuccina Country Resort

San Gimignano

$216

$245 total

includes taxes & fees

Oct 24 - Oct 25

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

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.

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

9. Hotel Le Renaie

San Gimignano

$100

$117 total

includes taxes & fees

Oct 26 - Oct 27

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

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

10. La Collegiata

San Gimignano

$159

$183 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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.

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

11. Hotel Casolare Le Terre Rosse

San Gimignano

$165

$189 total

includes taxes & fees

Oct 24 - Oct 25

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 swimming pool at night with a stone building in the background.

12. Tenuta Decimo

San Gimignano

$50

$60 total

includes taxes & fees

Oct 25 - Oct 26

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

A pool with a view of a vineyard and hills.

A view of a traditional brick building with arched doorways and wooden shutters.

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

13. Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

$86

$100 total

includes taxes & fees

Oct 27 - Oct 28

A stone building with a sign reading "hotel s.ino" and a door with a wrought iron gate.

A hotel lobby with a wooden reception desk, a black leather sofa, and a dining area in the background.

An outdoor seating area with tables and chairs under a tent, surrounded by potted plants and a stone wall.

An outdoor patio with stone walls, a stone lamp post, and a table with chairs.

14. Hotel San Lino

Volterra

$100

$117 total

includes taxes & fees

Oct 23 - Oct 24

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

A bedroom with a bed, a lamp, a chandelier, and curtains.

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

A view through a window of a stone wall with two towers, one with a pointed roof and the other with a rounded top.

15. Il Castagnolo Country B&B

San Gimignano

$93

$108 total

includes taxes & fees

Nov 13 - Nov 14

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

A rustic room with a stone ceiling, a bench, white tables, and a window with red curtains.

16. Hotel Il Castello

Certaldo Alto

$131

$150 total

includes taxes & fees

Oct 29 - Oct 30

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

A stone building with a terrace, outdoor seating, and a view of rolling hills.

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

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

17. Agriturismo Il Casolare di Bucciano

San Gimignano

$116

$133 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor patio with wicker furniture, a stone staircase, and a view of a historic building in the background.

A narrow street with historic buildings, a clear sky, and pedestrians.

A bar area with a large mirror, shelves with bottles, a clock, and a patterned floor.

A bar area with shelves of liquor bottles, a coffee machine, and a tray with tea sets and pastries.

18. Albergo Etruria

Volterra

$95

$110 total

includes taxes & fees

Oct 23 - Oct 24

A rustic stone building with a covered patio area featuring outdoor seating.

A swimming pool with white lounge chairs and a view of rolling hills.

An outdoor courtyard with a stone archway, a tiled pathway, and a view of a building in the background.

A cozy interior with a wooden reception desk, seating area, and exposed brick arches.

19. Agrihotel Il Palagetto

Volterra

$107

$124 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 lobby with a reception desk, a staircase, and seating areas.

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.

20. La Cisterna

San Gimignano City Centre

$89

$105 total

includes taxes & fees

Nov 5 - Nov 6

View all properties

Go beyond your typical stay in Il Castagno

Check out reviews of Il Castagno hotels guests love

Il Defizio

Gambassi Terme

10/10 Exceptional

Courtney

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 le Macine

Montaione

10/10 Exceptional

Michael

LHP Certaldo Resort

Certaldo

10/10 Exceptional

RAMONA

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

Hotel Casolare Le Terre Rosse

San Gimignano

10/10 Exceptional

charles

Poderi Arcangelo

San Gimignano

10/10 Exceptional

Cathy

Agriturismo Il Casolare di Bucciano

San Gimignano

10/10 Exceptional

We stayed here as part of our tour through Tuscany. Although we wanted to visit San Gimignano, we knew that it would be packed with tourists and bus tours, so we wanted to find a place close enough to visit the town, but away from the hectic crowds. Agriturismo Il Casolare di Bucciano perfectly suited those needs; we had a lovely view of San Gimignano from the grounds. Our GPS had trouble finding this place, because it is a rural address, but the personal connection always seems to work - a...

Jennifer

Albergo Etruria

Volterra

10/10 Exceptional

Steve

A swimming pool with lounge chairs and a stone building with a view of the mountains at sunset.

A bedroom with a brick ceiling, a large bed with a red bedspread, a wooden headboard, a TV mounted on the wall, and a window with curtains.

A stone building with a staircase leading to a second floor, surrounded by a stone wall and a paved area with steps.

A restaurant with arched brick ceilings and wooden tables, featuring a stone wall and large windows.

Albergo Villa Rioddi

Volterra

10/10 Exceptional

Got lots of information on where to travel around the area. Very helpful with questions (where to park, how to get to places etc.) I booked this hotel bc of the breakfast and it did NOT DISSAPOINT! So many local dishes and eggs, and then breakfast dessert with a choice of 4-5 cakes everyday! It was a little hike from the town not very well marked but could easily drive and find parking (Luka will tell you where's it free/cheap/convenient) Spent a day at the pool looking at volterra and...

Kriste

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

Tenuta Decimo

San Gimignano

10/10 Exceptional

Laura

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

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

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

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

Hotel Sovestro

San Gimignano

10/10 Exceptional

Mikhail

Il Castagnolo Country B&B

San Gimignano

10/10 Exceptional

Anonymous traveler

Hotel Le Renaie

San Gimignano

10/10 Exceptional

marley

Hotel San Lino

Volterra

10/10 Exceptional

Todd

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.

Hotel Villa San Giorgio

Poggibonsi

10/10 Exceptional

Arik

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

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

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.

Locanda Il Pino

San Gimignano City Centre

10/10 Exceptional

William

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

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

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.

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

Frequently Asked Questions

What hotels do travelers like in Il Castagno?

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

Can I book refundable accommodations in Il Castagno?

If you need the flexibility to change your travel plans to Il Castagno, most hotels provide refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in Il Castagno be like during my trip?

The warmest months in Il Castagno are usually August and July with an average temp of 73°F. January and February are the chilliest months when the average temp is 44°F. The rainiest months are November and October.

Why should I book my Il Castagno hotel with Hotels.com?

There are plenty of reasons to book your Il Castagno travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, 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.