The Best Hotels Closest to Castle of Oliveto in Castelfiorentino for 2026

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Our top choices for Castle of Oliveto hotels

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

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

1. Il Defizio

15.4 km from Castle of Oliveto

Courtney

AED 456

AED 514 total

includes taxes & fees

8 Oct - 9 Oct

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 kitchen with white cabinets, a wooden table, and a clock on the wall.

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

2. Capanna 1826

8 km from Castle of Oliveto

Richa

AED 343

AED 421 total

includes taxes & fees

28 Oct - 29 Oct

A person sitting by a swimming pool with a stone building in the background.

A person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.

An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

A sunset scene with a person holding a child, benches, and umbrellas in a park setting.

3. Hotel Borgo di Cortefreda Relais

13.1 km from Castle of Oliveto

Sergey

AED 484

AED 557 total

includes taxes & fees

24 Oct - 25 Oct

An outdoor café with tables and chairs, a whiteboard, and a door with a sign.

A cozy interior with a dining area, striped chairs, a rug, and a painting on the wall.

A restaurant with stone walls, framed artwork, and tables set for dining.

4. Locanda Il Pino

14.2 km from Castle of Oliveto

Thomas

AED 327

AED 380 total

includes taxes & fees

11 Oct - 12 Oct

A large building with a swimming pool, surrounded by greenery and outdoor lighting.

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.

A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.

5. LHP Certaldo Resort

5.9 km from Castle of Oliveto

Arash

AED 518

AED 595 total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a stone building.

A stone wall with a metal railing, overlooking a valley with trees and distant hills.

A stone building with a balcony, a stone wall, and a pathway leading to a fountain.

6. Villa San Filippo

14.2 km from Castle of Oliveto

Nadia

AED 237

AED 285 total

includes taxes & fees

31 Oct - 1 Nov

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

A swimming pool with clear water, surrounded by lounge chairs and trees.

A bedroom with a bed, bedside tables, a rug, and a view of the outdoors.

A kitchen area with a marble countertop, a stone wall, and a sign reading "Cooking Class".

7. Salvadonica - Borgo del Chianti

16.5 km from Castle of Oliveto

Jonathan

AED 386

AED 441 total

includes taxes & fees

3 Nov - 4 Nov

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

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.

A cozy dining area with a wooden table and chairs, a sofa, and a fireplace.

8. Agriturismo Il Casolare di Bucciano

16.3 km from Castle of Oliveto

"The views and quality of this agriturismo is simply outstanding. Peaceful and surreal, the view of San Gimigano are amazing. We had a wonderful time. Breakfast options could have been more varied for vegetarians and the staff member who greeted us on arrival could have been a little more welcoming! All other members of staff were outstanding. Did their best to accommodate us, including cooking special egg free dishes! Gratzie!"

Satnam

AED 428

AED 491 total

includes taxes & fees

1 Nov - 2 Nov

A dining area with wooden tables and chairs, brick arches, and large windows.

A bedroom with a large bed, a wooden desk, and a view of a vineyard through large arched windows.

A bedroom with a large bed, a desk, and a chair. There are multiple windows with curtains, and a view of trees and mountains outside.

A building with a white facade, a tiled roof, and a balcony with a railing. There is a door with an arch and a window with shutters.

9. Tenuta di Sticciano

5 km from Castle of Oliveto

Myca

AED 528

AED 601 total

includes taxes & fees

11 Oct - 12 Oct

An outdoor patio area with brick walls, stone flooring, and tables with red tablecloths.

A building with a tiled roof and a window, surrounded by greenery and a field of yellow flowers.

A cozy outdoor seating area with wicker furniture, a large umbrella, and stone flooring.

A small building with a tiled roof, a covered outdoor seating area with chairs and umbrellas, and a gravel courtyard with potted plants.

10. Country Hotel Borgo Sant'Ippolito

13.8 km from Castle of Oliveto

Evauna

AED 496

AED 567 total

includes taxes & fees

4 Oct - 5 Oct

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

A view from a covered outdoor area with a paved floor, leading to a garden with various plants and a distant landscape.

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

A stone building with a rustic exterior, surrounded by lush greenery and outdoor seating areas.

11. Hotel Villa San Giorgio

16.1 km from Castle of Oliveto

Arik

AED 226

AED 249 total

includes taxes & fees

3 Nov - 4 Nov

A garden with tall cypress trees, a variety of flowering plants, and a clear sky.

A spa room with a hot tub, wooden flooring, and a decorative window.

A wedding reception table set outdoors with floral arrangements and candles.

A villa with a swimming pool, surrounded by lush greenery and hills.

12. Relais Sassa al Sole

15.6 km from Castle of Oliveto

William Neill

AED 773

AED 850 total

includes taxes & fees

9 Oct - 10 Oct

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

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

A rustic room with a stone ceiling, a bench, white tables, and a window with red curtains.

A living room with a sofa, armchairs, a coffee table, and a painting on the wall.

13. Hotel Il Castello

5.6 km from Castle of Oliveto

Kenneth

AED 482

AED 551 total

includes taxes & fees

4 Oct - 5 Oct

A swimming pool with lounge chairs and umbrellas, a building with a balcony, and a stone pathway.

A dining table set with plates, cutlery, and glasses, surrounded by potted plants and a view of trees.

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.

14. Hotel Le Colline

15.5 km from Castle of Oliveto

Federico

AED 355

AED 416 total

includes taxes & fees

12 Oct - 13 Oct

A pool area with a sunset view, surrounded by trees and a distant mountain range.

A rural landscape with a small shed, trees, and a field.

A sunlit outdoor seating area with a pergola and lounge chairs.

A modern bedroom with a geometric-patterned headboard, a large bed, and a view of the outdoors through sheer curtains.

15. Le Mammole

15.3 km from Castle of Oliveto

Yuriy

AED 357

AED 393 total

includes taxes & fees

6 Oct - 7 Oct

A modern bedroom with a wooden floor, a bed with a headboard, a window with curtains, and a shower area with a towel rack.

A modern living room with leather furniture, a glass coffee table, and a white brick wall.

A modern hotel room with a bed, a desk, a chair, and a TV.

A modern bar area with purple seating, a laptop on a shelf, and a wine display.

16. Park Hotel Chianti

14.2 km from Castle of Oliveto

Manuel

AED 301

AED 356 total

includes taxes & fees

3 Nov - 4 Nov

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 pool with a view of rolling hills and distant buildings.

17. Poderi Arcangelo

8 km from Castle of Oliveto

Hector

AED 415

AED 477 total

includes taxes & fees

2 Nov - 3 Nov

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

A large, modern building with a blue roof, surrounded by lush green fields and trees.

A bedroom with a bed, a bedside table with a lamp, a chair, and a view of a balcony with wooden shutters.

A grassy area with a stone wall and a wooden fence.

18. Chianti Village Morrocco

15.4 km from Castle of Oliveto

Winonah

AED 292

AED 329 total

includes taxes & fees

4 Oct - 5 Oct

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

A table set for a meal with various cheeses, meats, and a bottle of wine, outdoors with a house in the background.

A bedroom with a large bed, a bathtub, a window with curtains, and a TV on the wall.

A dining area with a chandelier, tables, chairs, and a buffet table with food and drinks.

19. Borgo Elissa

9.9 km from Castle of Oliveto

Danit

AED 437

AED 501 total

includes taxes & fees

18 Oct - 19 Oct

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

An aerial view of a large, two-story house with a swimming pool, surrounded by lush greenery and fields.

A dining area with tables set for meals, a bar area with shelves of bottles, and a wooden cabinet.

A swimming pool surrounded by lush greenery and a forested hillside.

20. B&B La Fonte del Machiavelli

16.9 km from Castle of Oliveto

James

AED 428

AED 488 total

includes taxes & fees

4 Oct - 5 Oct

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Top Castle of Oliveto Hotel Reviews

Tenuta Moriano

10/10 Excellent

"Amazing stay! The staff were absolutely fantastic, Natalia was so helpful and so kind. We were sad we didn’t stay longer! Would highly recommend for your stay in Tuscany!"

VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.

10/10 Excellent

"Villa Belsole exceeds the listing. We were a big party of 18 made up of five families who have holidayed together several times previously and this property met our expectations 100%. We did make use of the option to have additional beds which provided further flexibility for the sleeping arrangements and meant parents could have separate rooms from the children in all cases. Communication with Enzo and Christina was perfect and although there was a small misunderstanding during check-in regarding the additional cost of electricity and water for the week this was quickly resolved. We took advantage of using the local cook on-site for one evening which was an excellent choice and we were able to adjust the menu to suit our party's tastes and dietary needs - the food was wonderful and plentiful. Indoor and outdoor dining tables, which could seat us all, were made good use of and the pool gave a welcome break from the high temperatures in August and has a view which never failed to look anything but spectacular. Aircon operates throughout the property in all the rooms and makes for a very comfortable nights sleep. The villa is perfectly positioned for day trips to Florence, Siena and Pisa with the local town of Certaldo having well stocked Supermarkets. A perfect holiday which both the parents and children thoroughly enjoyed - highly recommended. Thank you."

Casa Farsetti - Exclusive villa with private pool between Siena and Florence

10/10 Excellent

"Idyllisch gelegene Villa mit viel toskanischem Charme und liebevoller Einrichtung. Die Anlage ist perfekt, Poolbereich sehr groß und eine wunderschöne Aussicht. Ohne Klimaanlage ist es in den Schlafbereichen sehr warm, aber es werden genügend Ventilatoren zur Verfügung gestellt."

Villa in Chianti with private pool, walking to a restaurant Electric car charger

10/10 Excellent

"Villa idéalement située pour découvrir les beautés de la Toscane.Grande gentillesse et disponibilité des propriétaires.Magnifiques jardin et piscine avec vue imprenable de la terrasse.En famille (14) nous avons passé une merveilleuse semaine dans cette belle villa."

"A CASA DI FRANCA" PRIVATE VILLA IN CHIANTI A RURAL REFUGE FOR FAMILIES

10/10 Excellent

"Gambassi Terme was an incredible home with amazing views of the nearby vineyard. The rooms were chic with plenty of space for our large family. The outdoor spaces were elevated and relaxing and plenty of toys for the kids to play at the pool. And the wine from the vineyard was delicious. Would love to stay here again when visiting Tuscany. 10 out of 10.Christina"

Tenuta di Sticciano

10/10 Excellent

"Beautiful property and staff! They were sincere and kind and helpful. We really loved our stay there! Would definitely come again, and recommend them. Made for a memorable trip. Thank you! "

Other attractions near Castle of Oliveto

Teatro del Popolo

You can make plans for a show at Teatro del Popolo during your stay in Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area.

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Benozzo Gozzoli Museum

You can spend an afternoon studying the exhibits at Benozzo Gozzoli Museum in Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area.

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Tenuta Maiano

You can enjoy a tasting or tour at Tenuta Maiano during your travels to Montespertoli. Discover the beautiful countryside and wineries in this quaint area.

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Agricola Tamburini Emanuela

You can enjoy a tasting or tour at Agricola Tamburini Emanuela during your travels to Gambassi Terme. Discover the beautiful countryside and wineries in this quaint area.

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Church of Saint Jacob and Saint Philip

8.8/10 (3 reviews)

Church of Saint Jacob and Saint Philip is just one of the places to see in Certaldo, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and wineries in this culturally rich area.

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Museum of Sacred Art

6.0/10 (1 review)

You can study the exhibits at Museum of Sacred Art, a museum with a storied past, during your trip to Certaldo. Discover the beautiful countryside and wineries in this relaxing area.

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Casa del Boccaccio

8.6/10 (7 reviews)

You can browse the exhibits at Casa del Boccaccio, a museum with a storied past, during your trip to Certaldo. Discover the beautiful countryside and wineries in this relaxing area.

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Palazzo Pretorio

7.2/10 (5 reviews)

Find out about the history of Certaldo when you spend time at Palazzo Pretorio. Discover the beautiful countryside and wineries in this relaxing area.

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Frequently asked questions

What's the area like around Castle of Oliveto?

Castle of Oliveto is located in a historic area of Castelfiorentino known for its its beautiful countryside and selection of wineries. If you're looking for a convenient place to stay, check out the 32 hotels and other accommodations you'll find within a mile.

What's the best place to stay close to Castle of Oliveto?

Torre Rasa Agriturismo Apartments is one of the top choices for your stay based on our traveler data, and this apartment offers free parking and a seasonal outdoor pool. It's located 2.9 mi (4.7 km) from Castle of Oliveto. Other good choices within a few miles include Agriturismo Rebarco and Beautiful apartment for 6 people with pool, WIFI, TV and pets allowed, close to San Gimignano.

How many hotels should I expect to find close to Castle of Oliveto?

Expedia has 32 hotels and other accommodations within a mile from Castle of Oliveto.

If I need to cancel the hotel reservation for my stay near Castle of Oliveto, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Enter your dates, click on "Search", then use the filter option "fully refundable" to get the best deals available near Castle of Oliveto.

Where can I learn more about changing or cancelling my trip in the area near Castle of Oliveto?

For more information about picking new dates or cancelling your stay near Castle of Oliveto, go to https://www.expedia.com/service/.

What can I see and do near Castle of Oliveto?

You might want to spend some time browsing the exhibits at Benozzo Gozzoli Museum, Museum of Sacred Art, or Vine and Wine Museum. Casa del Boccaccio, Palazzo Pretorio, and Chiesa dei Santi Tommaso e Prospero are monuments to see when you're exploring the area around Castle of Oliveto. If you've got some time to explore the area around Castle of Oliveto, you may want to make a stop by Castello Sonnino, Tenuta Maiano, and Agricola Tamburini Emanuela.

Find hotels near Castle of Oliveto, Castelfiorentino from AED 249

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Our top choices for Castle of Oliveto hotels

1. Il Defizio

2. Capanna 1826

3. Hotel Borgo di Cortefreda Relais

4. Locanda Il Pino

5. LHP Certaldo Resort

6. Villa San Filippo

7. Salvadonica - Borgo del Chianti

8. Agriturismo Il Casolare di Bucciano

9. Tenuta di Sticciano

10. Country Hotel Borgo Sant'Ippolito

11. Hotel Villa San Giorgio

12. Relais Sassa al Sole

13. Hotel Il Castello

14. Hotel Le Colline

15. Le Mammole

16. Park Hotel Chianti

17. Poderi Arcangelo

18. Chianti Village Morrocco

19. Borgo Elissa

20. B&B La Fonte del Machiavelli

Top Castle of Oliveto Hotel Reviews

Tenuta Moriano

VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.

Casa Farsetti - Exclusive villa with private pool between Siena and Florence

Villa in Chianti with private pool, walking to a restaurant Electric car charger

"A CASA DI FRANCA" PRIVATE VILLA IN CHIANTI A RURAL REFUGE FOR FAMILIES

Tenuta di Sticciano

Other attractions near Castle of Oliveto

Teatro del Popolo

Benozzo Gozzoli Museum

Tenuta Maiano

Agricola Tamburini Emanuela

Church of Saint Jacob and Saint Philip

Museum of Sacred Art

Casa del Boccaccio

Palazzo Pretorio

Frequently asked questions