Hotels in Il Castagno

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Where to stay in Il Castagno?

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 a stone building in the background, surrounded by trees and outdoor seating.

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.

1. Hotel Casolare Le Terre Rosse

San Gimignano

$168

$191 total

includes taxes & fees

Oct 25 - Oct 26

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 courtyard with a lawn, seating area, and a weeping willow tree.

2. LHP Certaldo Resort

Certaldo

$128

$148 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

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

3. Hotel le Macine

Montaione

$84

$97 total

includes taxes & fees

Oct 22 - Oct 23

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

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.

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

4. Il Defizio

Gambassi Terme

$124

$140 total

includes taxes & fees

Oct 20 - Oct 21

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

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.

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

5. Boccioleto Resort&Spa - Place of Charme

Montaione

$71

$85 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

6. Tenuta Decimo

San Gimignano

$50

$60 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

A historic building with a central tower and arched windows.

7. Hotel Foresteria Volterra

Volterra

$92

$107 total

includes taxes & fees

Oct 20 - Oct 21

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 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.

8. Hotel Le Renaie

San Gimignano

$101

$117 total

includes taxes & fees

Oct 26 - Oct 27

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

A narrow street with stone buildings, a wooden bench with flowers, and a cobblestone path.

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.

9. Hotel San Lino

Volterra

$100

$117 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

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

10. Agriturismo Il Casolare di Bucciano

San Gimignano

$116

$134 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

11. Poderi Arcangelo

San Gimignano

$108

$125 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

12. La Collegiata

San Gimignano

$159

$183 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 bedroom with a bed, a nightstand, a vase with dried plants, and a wall mural of a landscape.

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.

13. Hotel Le Colline

San Gimignano

$97

$113 total

includes taxes & fees

Oct 25 - Oct 26

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

A restaurant with multiple tables set for dining, featuring a rustic wooden ceiling and stone walls.

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

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

14. Agrihotel Il Palagetto

Volterra

$107

$124 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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

A hotel room with a bed, a bedside table with a lamp, a small table with two glasses, and a chair.

15. Cappuccina Country Resort

San Gimignano

$206

$234 total

includes taxes & fees

Oct 20 - Oct 21

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 staircase with a wooden handrail and black balusters, leading to an upper floor.

16. Hotel Il Castello

Certaldo Alto

$131

$150 total

includes taxes & fees

Oct 20 - Oct 21

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 restaurant with a brick floor, white furniture, and a chalkboard menu.

17. Il Castagnolo Country B&B

San Gimignano

$93

$108 total

includes taxes & fees

Nov 13 - Nov 14

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

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

A hotel entrance with a glass door, a welcome mat, and two potted plants.

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

18. Albergo Etruria

Volterra

$95

$110 total

includes taxes & fees

Oct 20 - Oct 21

A narrow street with stone buildings, wooden barrels, and potted plants.

A narrow stone pathway leading to a building with a tiled roof and a lantern on the right.

A rustic interior with a stone archway leading to a dining area. A chalkboard sign on the wall reads "COLAZIONE 8-10 19:00 Buon Appetito!"

A stone-walled room with a wooden table and chairs, a large arched doorway, and a brick floor.

19. Fattoria San Donato

San Gimignano

$146

$166 total

includes taxes & fees

Oct 23 - Oct 24

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

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

20. La Cisterna

San Gimignano City Centre

$97

$114 total

includes taxes & fees

Nov 2 - Nov 3

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

LHP Certaldo Resort

Certaldo

10/10 Exceptional

RAMONA

Hotel Casolare Le Terre Rosse

San Gimignano

10/10 Exceptional

charles

Hotel le Macine

Montaione

10/10 Exceptional

Michael

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

A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.

A stone-walled room with a bench and a small shelf.

A stone building with a tiled roof, a gravel path leading to a wooden archway, and a sign reading "LA FONTE".

A round bar area with a central light fixture and a variety of bottles and glasses.

Borgo Pignano Volterra Tuscany

Volterra

10/10 Exceptional

Nithiwadee

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

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 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.

Hotel Sovestro

San Gimignano

10/10 Exceptional

Mikhail

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

Poderi Arcangelo

San Gimignano

10/10 Exceptional

Cathy

Albergo Etruria

Volterra

10/10 Exceptional

Steve

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.

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.

Casanova di Pescille

San Gimignano

10/10 Exceptional

This place is a gem! Wonderful service, this is Tuscany!! If you're looking for that, can't say enough about it. It's an old farmhouse that they've put a tremendous amount of work into. The room decor is all farm antigues that are beautiful! They also have wonderful Chianti that they make, and olives, and saffron!! The restaurant is wonderful too!! The town is about 2 km, and is lovely! You will need a car to get to this one.

Chris

A bedroom with a bed, a chair, a desk, and a window.

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.

A stone building with a rustic garden, a hanging light fixture, and a gravel path.

il Casale del Cotone

San Gimignano

10/10 Exceptional

Salvatore

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

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

A covered patio with outdoor seating, stone walls, and a view of the landscape.

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.

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

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

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

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

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

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

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

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

Tenuta Guardastelle

San Gimignano

10/10 Exceptional

Paige

A stone building with a sign reading "Vin Hotel." There are potted plants in front of the entrance.

A dining area with a round table and chairs, a vase with flowers, and a view of a stone building through an archway.

A dining area with a stone wall, a spiral staircase, and floral upholstered chairs.

A dining area with two ornate chairs, a table with a vase of red flowers, and a wall-mounted television.

Hotel Volterra In Superior

Volterra

10/10 Exceptional

Lone Lady

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.