Top 10 Hotels in Ancaiano (from $53) 2026 - Competitive Prices

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Our top choices for Ancaiano hotels

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

A vineyard with a sign that reads "La dolce vita" and a cart with wine bottles.

An outdoor dining area with tables and chairs, a covered walkway, and a view of a vineyard.

A vineyard with rows of grapevines and decorative hanging lights.

1. Hotel Ristorante La Dama nella Vigna

Monteriggioni

Amanda

$98 nightly

$114 total

Nov 3 - Nov 4

Total with taxes and fees

A courtyard with a white chair, a tree, and a building with arches and a brick wall.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

An interior corridor with arches, columns, and a brick wall.

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

2. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

$95 nightly

$114 total

Nov 16 - Nov 17

Total with taxes and fees

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

An outdoor patio with stone flooring, a table with chairs, and potted plants.

3. Hotel Borgo San Luigi

Monteriggioni

yekta

$102 nightly

$120 total

Nov 10 - Nov 11

Total with taxes and fees

A poolside area with lounge chairs, umbrellas, and a swimming pool.

A neatly made breakfast tray on a bed with a tray of bread, fruit, juice, and tea, in a room with a bed, curtains, and a painting on the wall.

A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.

A spacious dining area with multiple round tables, white tablecloths, and blue chair covers.

4. Hotel Il Piccolo Castello

Monteriggioni

Frank

$104 nightly

$123 total

Nov 13 - Nov 14

Total with taxes and fees

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.

A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.

A breakfast buffet with various pastries, fruits, and beverages.

5. Villa Sabolini

Colle di Val d'Elsa

Patricia

$80 nightly

$93 total

Nov 19 - Nov 20

Total with taxes and fees

A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.

A courtyard with stone buildings, a thatched-roof structure, and potted plants.

A wooden gazebo with a thatched roof overlooking a landscaped garden with trees and a view of hills.

A rural pathway flanked by tall trees and purple flowers, leading to a scenic view of the countryside.

6. Relais Castel Bigozzi

Monteriggioni

Nissan

$88 nightly

$105 total

Nov 21 - Nov 22

Total with taxes and fees

A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

A hotel entrance with a sign reading "HOTEL EXPO".

A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.

A modern living room with a glass coffee table, white sofas, and decorative plants.

7. Hotel Executive

Scacciapensieri

Andras

$69 nightly

$79 total

Nov 1 - Nov 2

Total with taxes and fees

A stone building with a swimming pool, surrounded by trees and a view of the landscape.

A stone building with a paved entrance and a well-maintained garden with potted plants.

A stone-walled terrace with a table set for two, a bottle, and candles.

A stone wall with a rustic stone building partially visible behind it.

8. Relais la Costa - Dimora Storica

Monteriggioni

Doug

$152 nightly

$172 total

Oct 22 - Oct 23

Total with taxes and fees

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."

9. Four Points by Sheraton Siena

Scacciapensieri

Ralph

$131 nightly

$147 total

Nov 7 - Nov 8

Total with taxes and fees

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

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

10. Palazzo di Valli

Siena

Luanne

$111 nightly

$125 total

Nov 21 - Nov 22

Total with taxes and fees

A buffet counter with various food items including pastries, a pie, and a bowl of eggs.

A conference room with rows of chairs, a projector, a whiteboard, and a podium.

A hotel room with a bed, bedside tables, a desk, and a chair.

A hotel entrance with a glass door, a metal frame, and a light fixture above.

11. Best Western Hotel San Marco

Siena

C.K.

$92 nightly

$105 total

Nov 7 - Nov 8

Total with taxes and fees

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A building with arched windows, a courtyard with a pond, and a metal fence.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

12. Hotel Casafrassi

Castellina in Chianti

Stuart

$56 nightly

$68 total

Oct 26 - Oct 27

Total with taxes and fees

A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

A bathroom with a sink, mirror, and shower.

A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.

13. Sangallo Park Hotel

Vico Alto

Marcio Tadeu

$92 nightly

$104 total

Nov 6 - Nov 7

Total with taxes and fees

A pathway lined with trees and a large pot in the center.

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

A breakfast buffet with pastries and a coffee machine.

A bedroom with a bed, bedside lamps, a wooden table, and a balcony with a view of greenery.

14. Villa Montarioso

Montarioso

Michael

$76 nightly

$89 total

Nov 15 - Nov 16

Total with taxes and fees

A stone building with a courtyard, surrounded by lush greenery and a hillside.

A window with white curtains, a view of buildings, and greenery.

A swimming pool with lounge chairs and umbrellas, stone buildings, and a clear sky.

A stone building with a balcony, surrounded by lush greenery and a view of distant hills.

15. Relais Le Macine di Stigliano

Sovicille

Rene

$142 nightly

$162 total

Nov 19 - Nov 20

Total with taxes and fees

A grand entrance with a staircase leading to a white building, surrounded by lush greenery and potted plants.

A swimming pool with a wooden deck, lounge chairs, and umbrellas.

A spacious indoor dining area with wooden ceiling beams, green and pink upholstered chairs, and a central bar area.

A rooftop terrace with outdoor seating, including a white sofa and wicker chairs, surrounded by potted plants and overlooking a cityscape.

16. Villa Ermellina Siena, a Tribute Portfolio Hotel

Camollia

Sebastian

$145 nightly

$163 total

Nov 14 - Nov 15

Total with taxes and fees

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A person relaxing in a hot tub with a view of a building and trees in the background.

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A poolside area with lounge chairs and a view of the night sky.

17. Belvedere di San Leonino

Castellina in Chianti

Kevork

$107 nightly

$124 total

Oct 27 - Oct 28

Total with taxes and fees

A courtyard with a statue, stone walls, and a reception sign.

A narrow cobblestone street flanked by stone buildings with arched windows and a central potted plant.

A wooden pathway leading to a pool area with a gazebo and potted plants.

An outdoor dining area with tables and chairs, surrounded by trees and a stone wall.

18. Relais Della Rovere

Colle di Val d'Elsa

Megan

$129 nightly

$147 total

Oct 30 - Oct 31

Total with taxes and fees

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

A modern living room with a sofa, a dining table, and a TV stand.

A modern kitchen with dark wooden cabinets, a dining table set with plates, glasses, and cutlery, and a vase of flowers on the right.

A spacious lobby with white furniture, a coffee station, and a view of the outdoors.

19. ApartHotel Anghel

Siena

Lauro

$63 nightly

$74 total

Nov 5 - Nov 6

Total with taxes and fees

A courtyard with a lemon tree, potted plants, and a building with arched windows.

A large, historic building with a covered patio and a well-maintained garden.

A room with a large window offering a view of a landscaped garden with trees and a pathway.

A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.

20. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Anita

$110 nightly

$126 total

Oct 31 - Nov 1

Total with taxes and fees

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Top Ancaiano Hotel Reviews

Il Chiostro del Carmine

8/10 Good

"Breakfast"

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good

"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."

La Certosa di Pontignano

10/10 Excellent

"Great location amazing place"

Poderi Arcangelo

10/10 Excellent

"Personnels très gentils, dégustation de vins super bon et intéressant, souper excellent, très bonne qualité nourriture, vin, huile d’olive. Je recommande cet endroit fortement"

Hotel Chiusarelli

8/10 Good

"It was OK for the price. The breakfast was so so, the parking very small and often full. The building is old and was making weird noises occasionally. The location was excellent: just outside LTZ but very close to all the points of interest."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

More cheap stays in Ancaiano

Cannon d'Oro

Via Montanini 28 Siena SI

$48 nightly

$56 total

Nov 21 - Nov 22

Total with taxes and fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

$71 nightly

$81 total

Nov 19 - Nov 20

Total with taxes and fees

7.8/10 Good! (453 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

$87 nightly

$99 total

Nov 1 - Nov 2

Total with taxes and fees

8.8/10 Excellent! (114 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

$88 nightly

$100 total

Nov 4 - Nov 5

Total with taxes and fees

10/10 Exceptional! (52 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

$149 nightly

$169 total

Oct 26 - Oct 27

Total with taxes and fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

Frequently asked questions

Where is the best place for a stay in Ancaiano?

Hotel Athena, located 6.4 mi (10.3 km) from the heart of Ancaiano, is a top choice for your stay based on our traveler data. Two other options for your trip to the area are La Certosa di Pontignano and NH Siena. See all available top hotels, or vacation rentals in Ancaiano.

What are some of the best vacation home rentals in Ancaiano?

Borgo Argiano: Visitors like this Ancaiano vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library. See all vacation rentals in Ancaiano.

If I need to cancel my hotel reservation in Ancaiano, will I receive a refund?

Yes, the majority of hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Ancaiano.

Where can I learn more about changing or cancelling my trip to Ancaiano?

For additional details about updating your trip to Ancaiano or cancelling it, go to https://www.expedia.com/service/.

What's the best pet-friendly place to stay in Ancaiano?

Biofarm Podere Ficareto is a top country house for people traveling with their pets, and offers an outdoor pool for its human guests. Other good choices to stay with your pet include Podere Ficareto Farm and Podere Ficareto Farm. See more pet-friendly hotel accommodations in Ancaiano.

What are some accommodations with pools in Ancaiano?

Poderi Arcangelo: Offers a snack bar/deli, 3 outdoor pools, and free self parking. Another choice with an onsite pool is Fattoria di Vegi. View all hotels with pools in Ancaiano.

How is it to stay in Ancaiano?

Travelers to Ancaiano will find plenty to explore and enjoy. In Ancaiano, there are 11 hotels and other accommodations to choose from. Find out more about Ancaiano.

What should I see while I'm in Ancaiano?

Places to visit in the wider area include Fortezza Medicea, Fontebranda, and Piazza del Campo. You'll also find Palazzo Pubblico and Banca Monte dei Paschi di Siena in the area. Check out what more to see and do in Expedia's Ancaiano guide.

What's the seasonal weather like in Ancaiano?

The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Ancaiano is 37 inches.

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Find hotels in Ancaiano from $53

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Ancaiano

Check prices for these dates

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Our top choices for Ancaiano hotels

1. Hotel Ristorante La Dama nella Vigna

2. La Certosa di Pontignano - Place of Charme

3. Hotel Borgo San Luigi

4. Hotel Il Piccolo Castello

5. Villa Sabolini

6. Relais Castel Bigozzi

7. Hotel Executive

8. Relais la Costa - Dimora Storica

9. Four Points by Sheraton Siena

10. Palazzo di Valli

11. Best Western Hotel San Marco

12. Hotel Casafrassi

13. Sangallo Park Hotel

14. Villa Montarioso

15. Relais Le Macine di Stigliano

16. Villa Ermellina Siena, a Tribute Portfolio Hotel

17. Belvedere di San Leonino

18. Relais Della Rovere

19. ApartHotel Anghel

20. Villa Scacciapensieri Boutique Hotel

Top Ancaiano Hotel Reviews

Il Chiostro del Carmine

Hotel Italia

Villa Ermellina Siena, a Tribute Portfolio Hotel

La Certosa di Pontignano

Poderi Arcangelo

Hotel Chiusarelli

Hotel Casolare Le Terre Rosse

Castello di Spaltenna- Small Luxury Hotels of the World

Four Points by Sheraton Siena

More cheap stays in Ancaiano

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

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