The Best Hotels Closest to Castellina Fortress in Castellina in Chianti - 2026 Updated Prices

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Our top choices for Castellina Fortress hotels

An outdoor seating area with wicker chairs and umbrellas, surrounded by lush greenery and stone pathways.

A dining table set with wine glasses, a candle, and a decorative vase.

A stone building with a balcony, potted plants, and a stone pathway leading to the entrance.

A pool area with lounge chairs, a wooden deck, and a clear view of the surrounding landscape.

1. Villa Di Capovento

3 km from Castellina Fortress

David

฿10,157

฿11,324 total

includes taxes & fees

14 Oct - 15 Oct

A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.

A pool area with lounge chairs, surrounded by well-maintained lawns and trees, with a view of rolling hills in the background.

A historic building with a courtyard, stone arches, and a tiled roof.

A bedroom with a wooden headboard, a large bed, two bedside tables with lamps, a wooden bench, a desk with a chair, and a window with curtains.

2. Palazzo Squarcialupi

< 0.1 km from Castellina Fortress

yvette

฿6,759

฿7,661 total

includes taxes & fees

21 Oct - 22 Oct

A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.

A spacious living room with striped sofas, a coffee table, and a chandelier.

A bench in a park with a lamp post and a building in the background.

A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.

3. Villa Casalecchi Country Hotel

1.9 km from Castellina Fortress

Alexandra

฿4,634

฿5,325 total

includes taxes & fees

9 Oct - 10 Oct

A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

A stone building with a large arched doorway, a bench, and a potted plant outside.

A stone staircase leading to a wooden balcony with a view of a mountainous landscape.

A stone-walled room with tables set for dining, a staircase, and a lamp.

4. Albergo Il Colombaio

0.4 km from Castellina Fortress

Christine

฿5,150

฿5,779 total

includes taxes & fees

6 Oct - 7 Oct

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

A dining area with a wooden table and chairs, a white sofa with cushions, and a staircase with a metal railing.

A modern kitchen with dark wooden cabinets, a dining table with chairs, and a vase of flowers on the table.

A bedroom with a bed, bedside tables, a chair, and a window with curtains.

5. Casa Vacanze Squarcialupi

0.2 km from Castellina Fortress

Jeffrey

฿4,228

฿4,877 total

includes taxes & fees

18 Oct - 19 Oct

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.

A dining area with a table set for two, featuring wine bottles and bread.

6. Castello La Leccia

3.3 km from Castellina Fortress

Eva

฿7,932

฿8,876 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a yellow sign reading "b&b erioico".

An aerial view of a town with a central square, surrounding buildings, and vineyards.

A stone building with a wooden door and shutters, a sign reading "b.v. eroico", and a number "19" on the wall.

A modern dining area with a wooden table, glass vases, and a staircase with glass railings.

7. L' Eroico

11.9 km from Castellina Fortress

Angela

฿4,351

฿5,088 total

includes taxes & fees

2 Nov - 3 Nov

A restaurant with large windows, a chandelier, and a table set for dining.

A swimming pool with a clear blue water surface, surrounded by a building with a tiled roof and a few trees in the background.

A modern outdoor seating area with a wooden pergola, a sofa, and a table.

A stone building with large windows, outdoor seating, and a gravel driveway.

8. Pensieri di Cavatina

16.2 km from Castellina Fortress

Jean

฿6,629

฿7,594 total

includes taxes & fees

1 Nov - 2 Nov

An open doorway leading to a balcony with a table and chairs, a white railing, and two wall-mounted light fixtures.

A marble staircase with a white console table and a potted plant.

A stone house with a small patio, a table, and a chair.

A pool with lounge chairs, a stone wall, and a building with arched windows.

9. Hotel Villa L'Avvenire

15 km from Castellina Fortress

Dakota

฿5,532

฿6,274 total

includes taxes & fees

29 Oct - 30 Oct

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

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.

10. Agriturismo San Sano

9.8 km from Castellina Fortress

Glen

฿2,452

฿2,848 total

includes taxes & fees

18 Oct - 19 Oct

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.

An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

11. The Club House

12.5 km from Castellina Fortress

Natalyn

฿12,039

฿13,621 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor dining area with a table and chairs, surrounded by greenery and a view of a building in the background.

A room with two white armchairs, a small white table with a lamp, a rug, and framed pictures on the wall.

A bedroom with a stone wall, a TV, a chandelier, a bed, a nightstand, and a window with curtains.

A living room with a sofa, a cabinet, and two wall-mounted lamps.

12. Chiantirooms Guesthouse

13.3 km from Castellina Fortress

Pasquale

฿3,254

฿3,730 total

includes taxes & fees

1 Nov - 2 Nov

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.

13. Relais la Costa - Dimora Storica

13.9 km from Castellina Fortress

Doug

฿5,182

฿5,889 total

includes taxes & fees

29 Oct - 30 Oct

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

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

A modern living room with a sofa, a lamp, and a view through an archway to a kitchen area.

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

14. Borgo Elissa

15.9 km from Castellina Fortress

Danit

฿3,994

฿4,582 total

includes taxes & fees

18 Oct - 19 Oct

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

A table set with wine glasses and a candle, viewed through a window with string lights.

A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

15. Tenuta CorteDomina

7.2 km from Castellina Fortress

Edgar

฿7,932

฿8,876 total

includes taxes & fees

1 Nov - 2 Nov

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

A room with two yellow sofas, a wooden floor, a large painting, a chandelier, and a patterned rug.

A hallway with a wooden floor, a painting on the wall, and a vase with flowers on a table.

A dining table with a variety of food and drinks, a vase with flowers, and a view of an outdoor patio with chairs and umbrellas.

16. Relais degli Angeli

16.6 km from Castellina Fortress

Manjeet

฿5,204

฿5,876 total

includes taxes & fees

11 Oct - 12 Oct

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

A pool area with lounge chairs and a service person attending to a guest.

A stone building with outdoor seating and a garden with roses.

17. Borgo San Felice Resort

16.5 km from Castellina Fortress

Cynthia

฿24,036

฿26,817 total

includes taxes & fees

25 Oct - 26 Oct

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

A table set for breakfast with various dishes, drinks, and a newspaper.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

18. Hotel Le Fontanelle

13.1 km from Castellina Fortress

Cristina

฿18,492

฿20,719 total

includes taxes & fees

11 Oct - 12 Oct

An outdoor patio with tables and chairs, surrounded by potted plants and a red building.

A courtyard with brick buildings, a stone wall, and a view of the surrounding town.

A brick building with three windows, a round blue window, and a sign on the wall.

A swimming pool with a clear view of the water, a metal structure on the right, and a landscaped area with chairs and plants in the background.

19. Borgo Grondaie

15.9 km from Castellina Fortress

Simon

฿2,794

฿3,187 total

includes taxes & fees

2 Nov - 3 Nov

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

A rustic stone building with a garden in front.

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

20. Belvedere di San Leonino

5.8 km from Castellina Fortress

Michelle Reene

฿4,106

฿4,743 total

includes taxes & fees

15 Oct - 16 Oct

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Top Castellina Fortress Hotel Reviews

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Palazzo Squarcialupi

10/10 Excellent

"Beautiful, clean hotel in the perfect location. The breakfast was wonderful and we enjoyed a delicious dinner on the terrace overlooking the pool and lovely grounds. The view is fantastic. We briefly visited the spa. Don't miss this! Our room was spacious and they even provided toothbrush and shaving kits. We would definitely return! Our greeting upon arrival from the staff was welcoming and I had a fantastic Aperol sprits from the small bar. I wish we had planned a longer stay!"

Belvedere di San Leonino

10/10 Excellent

"It was an amazing experience, we enjoyed it very much, Cristina was a superb host and super friendly and helpful, I highly recommend this place, it’s beautiful!!"

Agriturismo Villa Godenano - Pool & Suites

10/10 Excellent

"What a wonderful place to stay. From the free breakfast on the patio every morning, the customer service, to the convenience of walking into town, the views - no complaints. Great value, Grazie."

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Villa Casalecchi Country Hotel

8/10 Good

"The Villa itself is beautiful and is a gorgeous setting. However, their road off the main road is not paved or lit. We didn't have our own car as we had a car service but we walked in Castellina each night for dinner, which is about a 25 minute walk. Coming back in pitch black wasn't the most fun! Also, they state their rooms have AC but they're glorified fans and do not cool down the room. Other than these two things, it's a very rustic and authentic Tuscan Villa and the owners are wonderful!"

Locanda le Piazze

10/10 Excellent

"I’m not even sure where to start with this incredible property. It’s an absolute oasis in the heart of Chianti wine region. Theres an extremely well kept pool that overlooks the rolling hills of wineries. The staff are amazing, so accommodating, and predict your every need. The rooms are great and clean and perfect for a couple traveling to wine region. If you aren’t driving yourself, make sure to reach out to the hotel ahead of time to book any car services — transfers within the region are hard to come by but the hotel staff will be more than happy to help with enough lead time. Grazie mille for the wonderful stay! We will be staying here every time we are in the region!"

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

Villa Di Capovento

10/10 Excellent

"Beautiful property, lovely room with gorgeous view. Wonderful hostess Stella made us feel at home. Meals were terrifico and we can't wait to go back. Thank you!"

Other attractions near Castellina Fortress

Archaeological Museum of Chianti

8.0/10 (6 reviews)

You can browse the exhibits at Archaeological Museum of Chianti, a museum with a story of its own, during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area or enjoy its local tours.

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Via delle Volte

After visiting Via delle Volte, make a plan to see the other sights and activities in Castellina in Chianti. Discover the countryside and wineries in this quaint area.

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Walls of Monteriggioni

9.2/10 (5 reviews)

You can study the exhibits at Walls of Monteriggioni, a museum with a storied past, during your trip to Castellina in Chianti. Discover the beautiful countryside and wineries in this walkable area.

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Mazzei Winery

You can enjoy a tasting or tour at Mazzei Winery during your travels to Fonterutoli. You can enjoy the restaurants while in the area.

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Lilliano Estate Winery

You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.

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Necropolis of Poggino

After visiting Necropolis of Poggino, make a plan to see the other sights and activities in Castellina in Chianti. Discover the countryside and wineries in this relaxing area.

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Casina di Cornia Winery

You can enjoy a tasting or tour at Casina di Cornia Winery during your travels to Castellina in Chianti. Discover the countryside and wineries in this relaxing area.

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Isole e Olena Winery

You can enjoy a tasting or tour at Isole e Olena Winery during your travels to Barberino Tavarnelle. Discover the beautiful countryside in this quaint area or enjoy its local tours.

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Frequently asked questions

What's the area like around Castellina Fortress?

Castellina Fortress is located in Castellina in Chianti. Travellers like the surrounding area for its wineries. If you're looking for a convenient place to stay, take a look at the 65 hotels and other accommodation options you'll find within a mile.

What's the best place to stay close to Castellina Fortress?

Adjacent to Castellina Fortress, Palazzo Squarcialupi is one of the top choices for your stay based on our traveller data, and this hotel offers a winery and a full-service spa. Other good options close by include Hotel Colle Etrusco Salivolpi and Albergo Il Colombaio.

How many hotels are there near Castellina Fortress?

Expedia has 65 hotels and other accommodation options within a mile from Castellina Fortress.

If I need to cancel the hotel reservation for my stay near Castellina Fortress, will I receive a refund?

Yes, you'll find most room reservations are fully refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then you can filter by "fully refundable" to get the top deals on offer near Castellina Fortress.

What can I see and do near Castellina Fortress?

Explore landmarks like Castello della Paneretta, Walls of Monteriggioni and Montecalvario. Create some family memories at Chianti Observatory and Borgo di Vescine - Tenute di Castelvecchi. Stopping by Isole e Olena Winery, Casa Emma or Il Molino di Grace Winery is a fun way to see all the area has to offer.

Search Hotels Near Castellina Fortress, Castellina in Chianti

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Check prices for these dates

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Our top choices for Castellina Fortress hotels

1. Villa Di Capovento

2. Palazzo Squarcialupi

3. Villa Casalecchi Country Hotel

4. Albergo Il Colombaio

5. Casa Vacanze Squarcialupi

6. Castello La Leccia

7. L' Eroico

8. Pensieri di Cavatina

9. Hotel Villa L'Avvenire

10. Agriturismo San Sano

11. The Club House

12. Chiantirooms Guesthouse

13. Relais la Costa - Dimora Storica

14. Borgo Elissa

15. Tenuta CorteDomina

16. Relais degli Angeli

17. Borgo San Felice Resort

18. Hotel Le Fontanelle

19. Borgo Grondaie

20. Belvedere di San Leonino

Top Castellina Fortress Hotel Reviews

Borgo Vescine

Palazzo Squarcialupi

Belvedere di San Leonino

Agriturismo Villa Godenano - Pool & Suites

Fattoria di Vegi

Villa Casalecchi Country Hotel

Locanda le Piazze

Hotel Villa Campomaggio

Villa Di Capovento

Other attractions near Castellina Fortress

Archaeological Museum of Chianti

Via delle Volte

Walls of Monteriggioni

Mazzei Winery

Lilliano Estate Winery

Necropolis of Poggino

Casina di Cornia Winery

Isole e Olena Winery

Frequently asked questions