Hotels in Il Castagno

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Where to stay in Il Castagno?

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

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.

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

1. Il Defizio

Gambassi Terme

$126

$143 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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.

2. La Cisterna

San Gimignano City Centre

$104

$121 total

includes taxes & fees

Oct 24 - Oct 25

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.

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.

3. Hotel Casolare Le Terre Rosse

San Gimignano

$174

$198 total

includes taxes & fees

Oct 14 - Oct 15

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

4. Boccioleto Resort&Spa

Montaione

$99

$116 total

includes taxes & fees

Sep 28 - Sep 29

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

A swimming pool with sun loungers and umbrellas, surrounded by a wooden fence and greenery.

A building with a courtyard featuring potted plants and flowers.

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

5. Hotel Le Renaie

San Gimignano

$138

$159 total

includes taxes & fees

Sep 25 - Sep 26

An aerial view of a vineyard estate with terraced vineyards, a central building with multiple rooms, and a swimming pool.

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

A stone-walled building with a rustic appearance, surrounded by lush greenery and trees.

A rustic dining area with stone walls, wooden beams, and tiled flooring. There are several tables and chairs arranged for dining.

6. Hotel Pescille by Double Hospitality

San Gimignano

$136

$156 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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.

7. Hotel Leon Bianco

San Gimignano City Centre

$129

$149 total

includes taxes & fees

Oct 18 - Oct 19

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.

8. Tenuta Sovestro - Agriturismo e Winery

San Gimignano

$188

$212 total

includes taxes & fees

Oct 22 - Oct 23

A stone building with a paved pathway leading to an arched entrance.

A stone structure with a metal pot on top, a red carriage, and a view of a town in the background.

A buffet table with various food items, including pastries, bread, and fruits.

A stone building with a tiled roof, a lattice window, and a paved patio with wooden chairs.

9. Capanna 1826

San Gimignano

$107

$129 total

includes taxes & fees

Oct 7 - Oct 8

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 swimming pool with clear water, surrounded by stone walls and lush greenery, overlooking a scenic landscape.

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

10. Borgo Pignano Volterra Tuscany

Volterra

$520

$578 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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

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

11. Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

$128

$148 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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.

12. Hotel le Macine

Montaione

$108

$123 total

includes taxes & fees

Oct 1 - Oct 2

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

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

13. Hotel San Lino

Volterra

$102

$119 total

includes taxes & fees

Oct 21 - Oct 22

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 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.

14. Poderi Arcangelo

San Gimignano

$126

$145 total

includes taxes & fees

Oct 23 - Oct 24

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

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

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

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

15. Tenuta Decimo

San Gimignano

$57

$69 total

includes taxes & fees

Oct 4 - Oct 5

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

A table set for breakfast with a scenic view of hills and trees.

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.

16. Relais Santa Chiara Hotel by Double Hospitality

San Gimignano

$107

$126 total

includes taxes & fees

Oct 20 - Oct 21

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

17. Albergo Etruria

Volterra

$117

$134 total

includes taxes & fees

Oct 14 - Oct 15

A balcony with a view of the sunset, a pool, and a metal container with rocks.

A two-story building with a rustic facade, arched windows, and a tiled roof.

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.

18. Hotel Torciano Vecchio Asilo

San Gimignano

$249

$280 total

includes taxes & fees

Oct 20 - Oct 21

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.

19. La Collegiata

San Gimignano

$199

$227 total

includes taxes & fees

Oct 9 - Oct 10

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

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.

A framed historical photograph of a building with a chandelier above it.

20. Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

$94

$109 total

includes taxes & fees

Oct 12 - Oct 13

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

Borgo Pignano Volterra Tuscany

Volterra

10/10 Exceptional

Nithiwadee

Capanna 1826

San Gimignano

10/10 Exceptional

Jay

Tenuta Sovestro - Agriturismo e Winery

San Gimignano

10/10 Exceptional

Jennifer Olson

La Cisterna

San Gimignano City Centre

10/10 Exceptional

Old hotel in an old mountain top town. Given the limitations of this environment the Cisterna is a great little hotel that met all of our needs .The Cisterna is located in Cisterna Square in town close to sights, dining and a valley view walkway. The views to the valley from the rooms is amazing. The rooms are a good size and are modernized and comfortable. The staff is great (friendly and helpful). Many choices for dining close by (in the square) but others will require some minor hills and...

David

A person performing a yoga pose on a wooden deck with a view of a landscape.

A historic stone castle with a fortified wall, a courtyard, and surrounding lush green hills.

A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

Castelfalfi

Montaione

10/10 Exceptional

Ann

A table with breakfast items and drinks, set against a vineyard backdrop.

A bedroom with a bed, a desk, and a chair. There are windows with curtains, a television on the wall, and a view of the outdoors.

A large house with a terrace, surrounded by vineyards, and solar panels on the roof.

Podere La Quercia

San Gimignano

10/10 Exceptional

Angie

Boccioleto Resort&Spa

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 Casolare Le Terre Rosse

San Gimignano

10/10 Exceptional

charles

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

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.

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

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 Leon Bianco

San Gimignano City Centre

10/10 Exceptional

We loved this place! Getting here was a bit tricky, as the map we were given in the welcome email was of bad quality, so it didn't take us to the correct place right away, but we figured it out, very minor. I'm sure you can ask for a better quality map. When we arrived to check in, we were greeted by Lisa, who was oh so very helpful! She showed us where laundry was, asked all questions we had about WIFI and other hotel things, recommended us 3 terrific places to eat dinner on each of our 3...

Todd

Hotel Torciano Vecchio Asilo

San Gimignano

10/10 Exceptional

Necola

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.

Hotel Sovestro

San Gimignano

10/10 Exceptional

Mikhail

Albergo Etruria

Volterra

10/10 Exceptional

Steve

Hotel le Macine

Montaione

10/10 Exceptional

Michael

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

A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped garden and a view of hills.

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

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

Agriturismo Il Segreto di Pietrafitta

San Gimignano

10/10 Exceptional

Vicki

Hotel Pescille by Double Hospitality

San Gimignano

10/10 Exceptional

Jonathan

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

A landscaped garden with a fountain, stone pathways, and a view of distant hills during twilight.

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

A restaurant with multiple tables and chairs, a wall decorated with plates, and a buffet area with food items.

il Casale del Cotone

San Gimignano

10/10 Exceptional

Salvatore

Hotel Le Renaie

San Gimignano

10/10 Exceptional

marley

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.