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Sep 29 - Sep 30
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Sep 30 - Oct 1
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Our top choices for Ancaiano hotels

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.
Breakfast meal
Pool

1. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
Canada
Raman
CA $181
CA $210 total
includes taxes & fees
Oct 29 - Oct 30
Hotel Borgo San Luigi
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".
An outdoor dining area with tables and chairs, covered by a canopy, and surrounded by greenery.
A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.

2. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Susan
CA $104
CA $123 total
includes taxes & fees
Oct 25 - Oct 26
Hotel Executive
A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.
A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.
A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.
A breakfast buffet with various pastries, fruits, and beverages.

3. Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
Australia
Andrew
CA $182
CA $206 total
includes taxes & fees
Oct 19 - Oct 20
Villa Sabolini
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.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.
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.

4. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Leslie
CA $139
CA $166 total
includes taxes & fees
Oct 19 - Oct 20
La Certosa di Pontignano
A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.
A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.
A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.
A bathroom with a sink, mirror, and shower.

5. Sangallo Park Hotel

Sangallo Park Hotel
Vico Alto
United Kingdom
Linda
CA $140
CA $163 total
includes taxes & fees
Oct 25 - Oct 26
Sangallo Park Hotel
A rural pathway flanked by tall trees and purple flowers, leading to a scenic view of the countryside.
A wooden gazebo with a thatched roof overlooking a landscaped garden with trees and a view of hills.
A room with a woven basket on a round table, a wooden chair, and a wooden floor.
A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.

6. Relais Castel Bigozzi

Relais Castel Bigozzi
Monteriggioni
United States
Paul
CA $199
CA $230 total
includes taxes & fees
Oct 9 - Oct 10
Relais Castel Bigozzi
A modern hotel lobby with glass-top tables, a magazine, and a small plant.
A conference room with rows of chairs, a projector, a whiteboard, and a podium.
A hotel room with a bed, bedside tables, a desk with a chair, a television, and a window with curtains.
A modern building with a sign reading 'HOTEL SAN MARCO.'

7. Best Western Hotel San Marco

Best Western Hotel San Marco
Siena
United Kingdom
C.K.
CA $144
CA $167 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Hotel San Marco
A stone building with a swimming pool, surrounded by trees and a view of the landscape.
A spacious living room with a wooden staircase, a sofa, a dining table, and a radiator.
A stone wall with a rustic stone building partially visible behind it.
A stone building with a paved entrance and a well-maintained garden with potted plants.

8. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
Canada
Doug
CA $219
CA $249 total
includes taxes & fees
Oct 29 - Oct 30
Relais la Costa - Dimora Storica
A hotel entrance with a glass facade, a brown awning, and a garden with pink flowers.
A spacious living area with a sofa, a coffee table, and a view of buildings through large windows.
A spacious lobby with a reception desk, a staircase with a glass railing, and a wooden floor.
A hotel room with a bed, a desk, a chair, and a window with curtains.

9. Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
Colle di Val d'Elsa
Canada
Sheila
CA $119
CA $135 total
includes taxes & fees
Oct 12 - Oct 13
Hotel La Vecchia Cartiera
A person sitting in a corner of a room with tiled walls and a bench.
A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.
A fountain in a park with tall trees and a clear sky.
A poolside area with lounge chairs, umbrellas, and a swimming pool.

10. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
Canada
Frank
CA $187
CA $217 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Il Piccolo Castello
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.
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.

11. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
United States
Rita
CA $86
CA $105 total
includes taxes & fees
Oct 7 - Oct 8
Hotel Casafrassi
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 hotel room with a bed, bedside table, and a mirror. There is a small desk with a chair and a vase of flowers. The room has a modern design with a neutral color palette.
A modern kitchen with dark wooden cabinets, a dining table set with plates, glasses, and cutlery, and a vase of flowers on the right.

12. ApartHotel Anghel

ApartHotel Anghel
Siena
Netherlands
Lauro
CA $110
CA $127 total
includes taxes & fees
Oct 6 - Oct 7
ApartHotel Anghel
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 swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

13. Four Points by Sheraton Siena

Four Points by Sheraton Siena
Scacciapensieri
United States
Ralph
CA $210
CA $239 total
includes taxes & fees
Oct 27 - Oct 28
Four Points by Sheraton Siena
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 lobby with a reception desk, a large painting, a potted plant, and a patterned floor.

14. Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel
Camollia
United States
Katherine
CA $240
CA $272 total
includes taxes & fees
Oct 25 - Oct 26
Villa Ermellina Siena, a Tribute Portfolio Hotel
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.
An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

15. Palazzo di Valli

Palazzo di Valli
Siena
United States
Payton
CA $216
CA $246 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo di Valli
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A stone building with a window and a light fixture.
A pool surrounded by lush greenery and vineyards, with a stone building in the background.

16. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
Australia
Glen
CA $96
CA $112 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
A courtyard with a lemon tree, potted plants, and a building with arched windows.
A swimming pool surrounded by lush greenery and a stone pathway.
A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.
A large, historic building with a covered patio and a well-maintained garden.

17. Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel
Scacciapensieri
United Kingdom
Nigel
CA $240
CA $272 total
includes taxes & fees
Oct 18 - Oct 19
Villa Scacciapensieri Boutique Hotel
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.

18. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
Sovicille
United States
kevin
CA $300
CA $338 total
includes taxes & fees
Oct 2 - Oct 3
Relais Le Macine di Stigliano
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.
An outdoor dining area with tables and chairs, surrounded by trees and a stone wall.
A wooden pathway leading to a pool area with a gazebo and potted plants.

19. Relais Della Rovere

Relais Della Rovere
Colle di Val d'Elsa
Australia
Robert
CA $188
CA $213 total
includes taxes & fees
Oct 29 - Oct 30
Relais Della Rovere
An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.
A room with a sofa, a desk, a bunk bed, and a patterned floor.
A yellow building with stone pillars, multiple windows, and a statue in the garden.
A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.

20. Villa San Lucchese

Villa San Lucchese
Poggibonsi
United Kingdom
James
CA $135
CA $158 total
includes taxes & fees
Oct 30 - Oct 31
Villa San Lucchese
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Top Ancaiano Hotel Reviews

More cheap stays in Ancaiano

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
CA $82
CA $99 total
Oct 25 - Oct 26
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
CA $174
CA $200 total
Sep 30 - Oct 1
includes taxes & fees
7.8/10 Good! (442 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
CA $207
CA $236 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (108 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
CA $214
CA $244 total
Sep 30 - Oct 1
includes taxes & fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
CA $103
CA $248 total
Oct 20 - Oct 21
includes taxes & fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

Frequently asked questions

What is the best area to stay in Ancaiano?
The best area to stay in Ancaiano is within the historic hilltop town itself, particularly around the central Piazza della Cisterna and the surrounding narrow streets.This area offers an authentic Tuscan experience, with properties often housed in beautifully restored medieval buildings. You'll find a delightful mix of local trattorias, wine bars, and artisan shops within easy walking distance. The town's layout means you're never far from a stunning viewpoint overlooking the rolling hills of the Tuscan countryside.Couples looking for a romantic escape will find the historic centre particularly appealing. The evenings are quiet and intimate, superb for a leisurely dinner or a stroll through the lamp-lit alleys. Many accommodations here offer private terraces with breathtaking views, ideal for enjoying a glass of local wine.For those travelling with family, staying within the town walls provides a convenient and central base. Children will enjoy exploring the ancient streets and the sense of history, and you'll find it easy to pop back to your accommodation for naps or snacks.
When is the best time to go to Ancaiano?
The best time to visit Ancaiano is typically during the spring (April to June) and autumn (September to October) months.These periods offer pleasant weather, with warm days great for exploring the Tuscan countryside without the intense heat of summer. You'll find the landscapes particularly beautiful, with blooming wildflowers in spring and the rich colours of the harvest season in autumn. For those who appreciate good food and wine, autumn also brings grape and olive harvests, offering unique local experiences.Couples often find these seasons ideal for a romantic getaway. The milder temperatures are great for leisurely strolls through vineyards, cycling along quiet country roads, or enjoying al fresco dining at local trattorias. Spring and autumn also tend to be less crowded than the peak summer months, allowing for a more relaxed and intimate experience.For travellers looking for a more active holiday, spring and autumn are excellent for outdoor pursuits.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Ancaiano.
How much is the nightly rate at a Ancaiano hotel?
Prices for hotels in Ancaiano often vary, but you can find a great deal from CA $99 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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