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November 2026

December 2026

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Our top choices for Il Castagno holiday rentals

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

1. Tenuta Sant'Ilario

Gambassi Terme

Sergio

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

2. Casa Vacanze Le Case

San Gimignano

Andrew

₹8,994 total

includes taxes & fees

12 Nov - 13 Nov

A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a scenic view of hills and a cloudy sky.

3. Tenuta Quadrifoglio

Gambassi Terme

Geraldine

₹13,533 total

includes taxes & fees

13 Nov - 14 Nov

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

4. Palazzo Pacini

Colle di Val d'Elsa

John

₹11,497 total

includes taxes & fees

12 Dec - 13 Dec

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

5. Borgo Antico Residence

Certaldo Alto

jane

A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

6. Borgo San Giusto

Empoli

Lucy

₹8,513 total

includes taxes & fees

15 Nov - 16 Nov

A table with breakfast items and a view of rolling hills.

7. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

₹7,642 total

includes taxes & fees

18 Nov - 19 Nov

A view through a window of a building with a street scene, including trees and buildings in the background.

8. Palazzo Brunelleschi

Castelfiorentino

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

9. B&B Palazzo Tortoli

San Gimignano City Centre

Caroline

₹10,212 total

includes taxes & fees

1 Dec - 2 Dec

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

10. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

₹11,435 total

includes taxes & fees

11 Dec - 12 Dec

A historic stone building with a prominent tower, arched windows, and a tiled roof.

11. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

₹11,383 total

includes taxes & fees

15 Nov - 16 Nov

A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

12. AlbergoDiffusoVolterra

Volterra

Mia

₹17,396 total

includes taxes & fees

25 Nov - 26 Nov

A hallway with a wooden barrel, a white bench, a painting of a landscape, and a small table with a vase.

13. Sportland

Colle di Val d'Elsa

Giorgio

₹5,181 total

includes taxes & fees

12 Nov - 13 Nov

A bed with a floral bedspread, two wall-mounted lamps, and a window with sheer curtains.

14. Donna Nobile

San Gimignano City Centre

Treena

₹8,433 total

includes taxes & fees

8 Dec - 9 Dec

A table with a cheese board, bread, a bottle of wine, and a potted plant.

15. DomuS Miniato

San Miniato

Thomas

₹10,663 total

includes taxes & fees

1 Dec - 2 Dec

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

16. Palazzo al Torrione 2

San Gimignano City Centre

Klaus

₹12,858 total

includes taxes & fees

19 Nov - 20 Nov

A table with a tray of pastries, a teapot, cups, and water bottles by a window with a view of greenery.

17. B&B Il Moscondoro

Montopoli in Val d'Arno

Manuel

₹8,498 total

includes taxes & fees

25 Nov - 26 Nov

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Find holiday rentals that suit your style

Top Il Castagno Hotel Reviews

An outdoor dining area with tables and chairs, a brick wall, and a view of the landscape.

Hotel Il Castello

Certaldo Alto

10/10 Excellent

Staying at Hotel Il Castello was a step back into history - a beautiful appointed historic building that had been sympathetically made over into a hotel/bar/restaurant, with panoramic views over Lower Certaldo. The bedrooms very clean, with rustic charm and furnishings. Modern functioning shower, TV, and AIRCON unit which was very welcome in the intensive 30+ degree heat of the day and night. The background music in the restaurant/bar always playing Jazz music - which, whilst not my favourite...

peter

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

Albergo Etruria

Volterra

10/10 Excellent

My partner and I spent one night in Volterra and we could not believe our luck when we walked in to the Albergo Etruria. We were made to feel immediately welcome and a family feeling permeated our whole time there. The hotel is imaginatively and beautifully decorated, very clean and comfortable, situated in a wonderful location and there is an attention to detail which is very rare nowadays. A beautiful feeling of tranquility exists throughout the hotel. Our room, 26 'Il balconcino', was...

Anonymous traveller

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

Agriturismo Il Casolare di Bucciano

San Gimignano

10/10 Excellent

Anish

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

Il Castagnolo Country B&B

San Gimignano

10/10 Excellent

This place is stunning! Laura looked after us superbly and nothing was too much trouble. The property make their own white wine and olive oil which were delicious. Breakfast offered a good continental selection and the coffee was incredible! Pool was a welcome touch and offered plentiful space to relax and unwind. Our room was a little small and was the basic room. Our friend had a larger room so make sure to check that. It’s only around 12-15 rooms. Main tip is you must have a car! We banked on...

Owen

A poolside area with lounge chairs and umbrellas, surrounded by a landscaped garden with red flowers.

Poderi Arcangelo

San Gimignano

10/10 Excellent

Stayed in the rooftop window room for 2 nights in the annex which wasn't ideal as the place was full... but it was a full for a reason. What a place - unbelievable views, breakfast was good and the dinner was top tier. The free wine tasting on the terrace was a particularly nice touch. We stayed here for 2 nights just after our wedding in Puglia and couldn't be happier with it as a place to unwind. Staff very attentive/knowledgable. Pool had a great view (starting to get a bit colder now...

Roy

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

Tenuta Decimo

San Gimignano

8/10 Good

Victoria

A yellow building with stone pillars, multiple windows, and a statue in the garden.

Villa San Lucchese

Poggibonsi

10/10 Excellent

Anonymous traveller

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

Hotel Sovestro

San Gimignano

10/10 Excellent

Hotel Sovestro is a friendly, relaxing place with two swimming pools and an indoor and outdoor breakfast area. Linked to the hotel next door is a lovely restaurant. Our stay was perfect at the hotel. The room was spacious and comfortable with a balcony overlooking the Tuscan countryside. The continental breakfast choice is outstanding and the entire hotel is kept very clean and up together. The walk to San Gimignano was a little further than we anticipated but it can be done in a leisurely 30...

Ruth

A cozy living room with large windows, a dining area, and a kitchen.

Torraccia di Chiusi

San Gimignano

10/10 Excellent

After the drive from Pisa airport, the drive up the 4km track led to a most stunning property. We were immediately welcomed by Stefano (and two cold beers!) and the hospitality continued throughout our stay. The five course Tuscan dinner every evening was worth every cent and how amazing were the team in making sure everything was perfect?! The pool was beautiful with stunning views. Truly an incredible location, breakfast, hosts, staff and home-grown, home-made food and drink. Thank you for...

David

A swimming pool, steps, and a grassy area with umbrellas.

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Excellent

Charles

Palazzo Pacini

Colle di Val d'Elsa

10/10 Excellent

A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.

Borgo san Benedetto

Montaione

10/10 Excellent

we would live here if we could. beautiful family run place, far more care and attention to every little detail than you would ever expect in even the very best hotels. beautiful grounds set in vineyard and olive groves, resident animals, fantastic restaurant onsite and lovely staff. the setting is so beautiful that one afternoon we got back to our apartment to find people taking selfies with our apartment door. our one suggestion would be to designate one of the pools as adults only as it did...

Claire

A pool area with a view of the countryside, surrounded by a wooden deck and outdoor furniture.

Poderi Arcangelo Glamping

San Gimignano

10/10 Excellent

Amazing place to stay. Simple and unpretentious. Clean, comfortable and modern. Great views (room and bar terrace) and nice staff. Glamping pods are separate from the main house and feel very private and secluded. Beautiful setting overlooking the hills and vineyards. Room (Olive suite) had a coffee machine and mini fridge with complimentary drinks/snacks. Large outdoor wrap-around terrace which got sun all day and late into the evening. Views overlooking the vineyards and rolling hills....

Craig

Find out more about Il Castagno

Holiday Rentals in Il Castagno

Search for holiday rentals in Il Castagno on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Il Castagno using one of the methods below:

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Frequently Asked Questions

Are there holiday rentals in Il Castagno?

Yes, there are holiday rentals close to the most popular sights in Il Castagno, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Il Castagno?

Explore the area and family-friendly sights such as Il Fiaschetto, or get out into nature at a spot like Sentierelsa Trail. In the wider area, you’ll find Monastery of San Vivaldo and Castelfalfi Golf Course.

What’s a holiday rental in Il Castagno like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Il Castagno. Holiday rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.

Search Holiday Rentals in Il Castagno

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Il Castagno holiday rentals

1. Tenuta Sant'Ilario

2. Casa Vacanze Le Case

3. Tenuta Quadrifoglio

4. Palazzo Pacini

5. Borgo Antico Residence

6. Borgo San Giusto

7. Chianti Village Morrocco

8. Palazzo Brunelleschi

9. B&B Palazzo Tortoli

10. Antica Pieve B&B

11. Materia Rooms San Gimignano

12. AlbergoDiffusoVolterra

13. Sportland

14. Donna Nobile

15. DomuS Miniato

16. Palazzo al Torrione 2

17. B&B Il Moscondoro

Find holiday rentals that suit your style

Top Il Castagno Hotel Reviews

Hotel Il Castello

10/10 Excellent

Find out more about Il Castagno

Holiday Rentals in Il Castagno

Frequently Asked Questions

Are there holiday rentals in Il Castagno?

What’s there to see and do in Il Castagno?

What’s a holiday rental in Il Castagno like?