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 garden with stone steps, outdoor seating, and a variety of plants.

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

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

1. Villa Di Capovento

1.8 mi from Castellina Fortress

David

£249

includes taxes & fees

15 Oct - 16 Oct

A pool with clear water and a row of white lounge chairs facing a scenic hillside view.

A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.

A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

2. Palazzo Squarcialupi

< 0.1 mi from Castellina Fortress

yvette

£172

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 hallway with a wooden altar, benches, and a carpet with a floral pattern.

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

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

3. Villa Casalecchi Country Hotel

1.2 mi from Castellina Fortress

Alexandra

£120

includes taxes & fees

16 Oct - 17 Oct

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

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

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

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

4. Albergo Il Colombaio

0.3 mi from Castellina Fortress

Christine

£112

includes taxes & fees

12 Oct - 13 Oct

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

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

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

A modern two-story residential building with a stone facade, a well-maintained garden with hedges and grass, and a clear sky.

5. Casa Vacanze Squarcialupi

0.1 mi from Castellina Fortress

Jeffrey

£110

includes taxes & fees

2 Nov - 3 Nov

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

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

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

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

6. Castello La Leccia

2.1 mi from Castellina Fortress

Eva

£194

includes taxes & fees

3 Nov - 4 Nov

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

A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

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

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

7. L' Eroico

7.4 mi from Castellina Fortress

Angela

£115

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A building with a sign that reads "PENSIER ECAVATINA."

8. Pensieri di Cavatina

10.1 mi from Castellina Fortress

Jean

£169

includes taxes & fees

3 Nov - 4 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 circular stone fountain with water jets in a garden setting.

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

9. Hotel Villa L'Avvenire

9.3 mi from Castellina Fortress

Dakota

£138

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 stone building with a wooden door, outdoor seating, and a pergola with vines.

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.

10. Agriturismo San Sano

6.1 mi from Castellina Fortress

Glen

£60

includes taxes & fees

21 Oct - 22 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.

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

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

11. The Club House

7.8 mi from Castellina Fortress

Natalyn

£301

includes taxes & fees

3 Nov - 4 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 wall with a rustic stone building partially visible behind it.

A spacious living room with a wooden staircase, a sofa, a dining table, and a radiator.

12. Relais la Costa - Dimora Storica

8.6 mi from Castellina Fortress

Doug

£133

includes taxes & fees

29 Oct - 30 Oct

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

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

A two-story building with a balcony, a staircase, and a gated entrance.

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

13. Chiantirooms Guesthouse

8.3 mi from Castellina Fortress

Pasquale

£84

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

14. Tenuta CorteDomina

4.5 mi from Castellina Fortress

Edgar

£200

includes taxes & fees

2 Nov - 3 Nov

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

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

15. Borgo Elissa

9.9 mi from Castellina Fortress

Danit

£103

includes taxes & fees

19 Oct - 20 Oct

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

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

A bathroom with a large bathtub, wooden flooring, and a chandelier.

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

10.3 mi from Castellina Fortress

Manjeet

£133

includes taxes & fees

11 Oct - 12 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 pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

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

17. Hotel Le Fontanelle

8.1 mi from Castellina Fortress

Cristina

£411

includes taxes & fees

11 Oct - 12 Oct

A historic stone building with multiple windows and a courtyard.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

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

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

18. Borgo San Felice Resort

10.2 mi from Castellina Fortress

Cynthia

£581

includes taxes & fees

25 Oct - 26 Oct

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.

A rustic stone building with a garden in front.

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

19. Belvedere di San Leonino

3.6 mi from Castellina Fortress

Michelle Reene

£107

includes taxes & fees

15 Oct - 16 Oct

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A room with a view of a forest through a window, a table with a lamp, and a chair.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

20. Dievole Wine Resort

5 mi from Castellina Fortress

Marissa

£234

includes taxes & fees

28 Oct - 29 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!"

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!"

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10/10 Excellent

"We had a wonderful stay at this outstanding villa and its guest houses near the lovely town of Castellina in Chianti in Italy. The property is over-the-top beautiful, with buildings and outdoor spaces that embrace the sloping terrain. Every addition and renovation feels thoughtful and lovingly done. The quality of everything is of the highest quality. Nothing was cheaply done!Our group of 18 had plenty of room and never felt cramped. We made full use of the expansive pool, cabanas, more than enough chaises and chairs on many decks, top tier huge umbrellas, as well as the two barbecues and pizza oven. There was space to gather and enjoy one another’s company, with separate living areas when we wanted a quieter moment. The main kitchen was all well stocked for at least 25 people. It had 2 frigs and 2 freezers. They even had some oil, salt, coffee, etc supplies to get started. There were washer and dryers in each building along with the bar area. The photos don’t fully show the newer improvements to the property. There is now an enclosed bar by the pool with glasses and dishes to serve 25 people. An addition to guest house #2 has also created two separate living spaces with bedrooms. The 5 new cabanas by the pool were of highest quality and they had lovely soft cushions. The manager, Raefela was just amazing! Always there to answer or to help.I know you will enjoy this fantastic place as much as we did! It is the most private place we have ever stayed at."

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!"

Castello di Fonterutoli Wine Resort

10/10 Excellent

"Beautiful property! Enjoyed sunset on the way back from the wine tour and tasting! Amazing dinner and breakfast, again with a phenomenal view of the Tuscan landscape! Very comfortable and spacious room!"

Borgo di Pietrafitta Relais

10/10 Excellent

"Amazing property! Just what you imagined Tuscany would look like."

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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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. Relais la Costa - Dimora Storica

13. Chiantirooms Guesthouse

14. Tenuta CorteDomina

15. Borgo Elissa

16. Relais degli Angeli

17. Hotel Le Fontanelle

18. Borgo San Felice Resort

19. Belvedere di San Leonino

20. Dievole Wine Resort

Top Castellina Fortress Hotel Reviews

Borgo Vescine

Palazzo Squarcialupi

Agriturismo Villa Godenano - Pool & Suites

Fattoria di Vegi

Villa Casalecchi Country Hotel

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Villa Di Capovento

Castello di Fonterutoli Wine Resort

Borgo di Pietrafitta Relais

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