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Find Hotels with Pool in Chianti Region

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Check availability on Chianti Region Hotels with Pool

Tonight
19 Sept - 20 Sept
Tomorrow
20 Sept - 21 Sept
Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct

Our top choices for Chianti Region hotels with a pool

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
£71
includes taxes & fees
19 Oct - 20 Oct
Borgo di Pietrafitta Relais

2. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
£109
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino

3. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
  • Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.
£162
includes taxes & fees
13 Oct - 14 Oct
Relais Vignale & Spa

4. La Pensione di Vignamaggio

La Pensione di Vignamaggio
Panzano in Chianti
  • Dive into poolside tranquility with a seasonal outdoor pool nestled among gardens and a charming terrace at this Italian retreat.
£183
includes taxes & fees
20 Oct - 21 Oct
La Pensione di Vignamaggio

5. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
  • Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.
£156
includes taxes & fees
20 Oct - 21 Oct
Hotel Villa Campomaggio

6. Azienda agricola la camporena

Azienda agricola la camporena
Greve in Chianti
£122
includes taxes & fees
7 Oct - 8 Oct
Azienda agricola la camporena

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
£232
includes taxes & fees
7 Oct - 8 Oct
Chapter Chianti, a Member of Design Hotels

8. Villa Le Barone

Villa Le Barone
Greve in Chianti
  • Dive into luxury at this Tuscan retreat with 2 outdoor pools, mountain views, and a poolside bar for ultimate relaxation.
£197
includes taxes & fees
11 Oct - 12 Oct
Villa Le Barone

9. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
  • Refreshing infinity pool with breathtaking views awaits at this charming Tuscan farm stay with winery.
£173
includes taxes & fees
20 Sept - 21 Sept
Castello Vicchiomaggio

10. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
  • Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.
£60
includes taxes & fees
18 Oct - 19 Oct
Agriturismo San Sano
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Choose what matters most at hotels with a pool in Chianti Region

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Chianti Region

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
£71
includes taxes & fees
19 Oct - 20 Oct
Borgo di Pietrafitta Relais

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
£60
includes taxes & fees
18 Oct - 19 Oct
Agriturismo San Sano

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
£93
includes taxes & fees
18 Oct - 19 Oct
Villa Casagrande Resort & SPA

Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
£162
includes taxes & fees
13 Oct - 14 Oct
Relais Vignale & Spa

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
£109
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
£173
includes taxes & fees
20 Sept - 21 Sept
Castello Vicchiomaggio

Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
£57
includes taxes & fees
22 Sept - 23 Sept
Palagina la cascina

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
£93
includes taxes & fees
20 Sept - 21 Sept
Hotel Colle Etrusco Salivolpi

La Pensione di Vignamaggio

La Pensione di Vignamaggio
Panzano in Chianti
£183
includes taxes & fees
20 Oct - 21 Oct
La Pensione di Vignamaggio

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
£133
includes taxes & fees
19 Oct - 20 Oct
Castello di Tornano Wine Resort
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4-star hotels with pools in Chianti Region

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
£109
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
£93
includes taxes & fees
18 Oct - 19 Oct
Villa Casagrande Resort & SPA

Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
£162
includes taxes & fees
13 Oct - 14 Oct
Relais Vignale & Spa

Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
£156
includes taxes & fees
20 Oct - 21 Oct
Hotel Villa Campomaggio

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
£94
includes taxes & fees
18 Oct - 19 Oct
Ultimo Mulino Wellness Country Hotel

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
£94
includes taxes & fees
19 Oct - 20 Oct
Villa I Barronci Resort & Spa

Villa San Lucchese

Villa San Lucchese
Poggibonsi
£115
includes taxes & fees
14 Oct - 15 Oct
Villa San Lucchese

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
Tavarnelle Val di Pesa
£120
includes taxes & fees
7 Oct - 8 Oct
Hotel Borgo di Cortefreda Relais

Palagina la Dimora

Palagina la Dimora
Figline e Incisa Valdarno
£108
includes taxes & fees
28 Sept - 29 Sept
Palagina la Dimora

Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
£110
includes taxes & fees
19 Oct - 20 Oct
Villa Sabolini
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5-star hotels with pools in Chianti Region

Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
£232
includes taxes & fees
7 Oct - 8 Oct
Chapter Chianti, a Member of Design Hotels

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
£333
includes taxes & fees
19 Oct - 20 Oct
Castello di Spaltenna- Small Luxury Hotels of the World

LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
£119
includes taxes & fees
19 Oct - 20 Oct
LHP Certaldo Resort

Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
£420
includes taxes & fees
11 Oct - 12 Oct
Hotel Le Fontanelle

Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
£533
includes taxes & fees
16 Oct - 17 Oct
Pieve Aldina - Relais & Châteaux

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
£464
includes taxes & fees
20 Oct - 21 Oct
Borgo Scopeto Wine & Country Relais

Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
£622
includes taxes & fees
11 Oct - 12 Oct
Borgo San Felice Resort

Borgo Vescine

Borgo Vescine
Radda in Chianti
£407
includes taxes & fees
20 Oct - 21 Oct
Borgo Vescine

COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
£762
includes taxes & fees
17 Oct - 18 Oct
COMO Castello Del Nero

The Club House

The Club House
Castelnuovo Berardenga
£598
includes taxes & fees
20 Oct - 21 Oct
The Club House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"very nice historic hotel with great views of the country side and great atmphere. Room size and ammenities were wonderful. The breakfeast was great. Restaurant was nice with historic dishes. Only down side was the gluten and nut free options were limited...mainly for gluten sufferers, since the only gluten free pasta is Penne, which is not great for all dishes and frustratingsince Italy produces a very large variety of great gluten free pasta shapes. Also, my travel partner and I did the same pasta, one gluten free (penne) and one not gluten free. The non-gluten-free pasta came beautifully presented, while the gluten-free pasta came like it was thrown together last minute… like as if you were sitting at your own kitchen table. Impression given with the dinner is that people with allergies, are more a bit of a bother, and the typical mission in Italy, to give visitors an excellent culinary experience, is more less abandoned for people with allergies. that said, accommodating allergies is very difficult these days and at least the menu was clear about which foods contain which allergens."
edward 2-night trip
Posted 1 day ago
Castello Vicchiomaggio
Palagina la Dimora

Palagina la Dimora

8/10 Good
"Nice property to relax. Pool is nice. Breakfast is meh but works. Room was spacious although felt outdated and lacking lighting. Some staff were very helpful while some could have been more friendly."
Rayvant 1-night trip
Posted 2 days ago
Palagina la Dimora
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."
David 3-night trip
Posted 4 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"Very nice property"
Ali 1-night trip
Posted 5 days ago
Relais Vignale & Spa
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."
Lauren 3-night trip
Posted 8 days ago
COMO Castello Del Nero
Borgo Vescine

Borgo Vescine

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."
Nadege 1-night trip
Posted 9 days ago
Borgo Vescine
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Excellent stay with wonderful , friendly staff!"
Kathleen 3-night trip
Posted 10 days ago
Villa Le Barone
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"This resort is one of the most beautiful properties I have ever stayed in. Free use of the spa just was icing on the cake! Great breakfast spread and our dinner in the restaurant was delicious! We will be back!!"
Jayni 2-night trip
Posted 10 days ago
Hotel Villa Campomaggio
Villa Il Palagio

Villa Il Palagio

10/10 Excellent
"Great loved everything thank you!"
Amber 2-night trip
Posted 12 days ago
Villa Il Palagio

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