A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region Hotel with Pool

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Chianti Region Hotel with Pool

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

Our top choices for Chianti Region hotels with a pool

1. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
  • Refreshing infinity pool with breathtaking views awaits at this charming Tuscan farm stay with winery.
HK$1,375
HK$1,512 total
includes taxes & fees
1 Sept - 2 Sept
Castello Vicchiomaggio

2. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
HK$1,041
HK$1,181 total
includes taxes & fees
13 Sept - 14 Sept
Borgo di Pietrafitta Relais

3. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
  • Sun-kissed pools in tuscan splendour beckon with historic charm and breathtaking views.
HK$1,084
HK$1,247 total
includes taxes & fees
27 Aug - 28 Aug
Palazzo Leopoldo Dimora Storica & Spa

4. Palagina la Dimora

Palagina la Dimora
Figline e Incisa Valdarno
  • Soak in panoramic bliss from this seasonal mountain pool with adjacent winery and poolside cocktails.
HK$518
HK$588 total
includes taxes & fees
1 Sept - 2 Sept
Palagina la Dimora

5. 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.
HK$1,512
HK$1,941 total
includes taxes & fees
21 Aug - 22 Aug
Relais Vignale & Spa

6. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
HK$899
HK$1,017 total
includes taxes & fees
21 Aug - 22 Aug
Hotel Colle Etrusco Salivolpi

7. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
HK$1,075
HK$1,237 total
includes taxes & fees
26 Aug - 27 Aug
Belvedere di San Leonino

8. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
  • Dive into year-round pool perfection with indoor and seasonal outdoor swimming options at this elegant Tuscan retreat.
HK$979
HK$1,132 total
includes taxes & fees
23 Aug - 24 Aug
Hotel Palazzo San niccolò & Spa

9. 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.
HK$1,721
HK$1,947 total
includes taxes & fees
31 Aug - 1 Sept
Villa Le Barone

10. Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
  • Sip poolside bliss at this luxury Tuscan retreat where serene mountain views frame your aquatic sanctuary.
HK$1,408
HK$1,603 total
includes taxes & fees
25 Aug - 26 Aug
Villa I Barronci Resort & Spa
View all properties

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
HK$1,041
HK$1,181 total
includes taxes & fees
13 Sept - 14 Sept
Borgo di Pietrafitta Relais

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
HK$1,375
HK$1,512 total
includes taxes & fees
1 Sept - 2 Sept
Castello Vicchiomaggio

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
HK$1,075
HK$1,237 total
includes taxes & fees
26 Aug - 27 Aug
Belvedere di San Leonino

Palagina la Dimora

Palagina la Dimora
Figline e Incisa Valdarno
HK$518
HK$588 total
includes taxes & fees
1 Sept - 2 Sept
Palagina la Dimora

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
HK$899
HK$1,017 total
includes taxes & fees
21 Aug - 22 Aug
Hotel Colle Etrusco Salivolpi

Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
HK$1,512
HK$1,941 total
includes taxes & fees
21 Aug - 22 Aug
Relais Vignale & Spa

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
HK$1,084
HK$1,247 total
includes taxes & fees
27 Aug - 28 Aug
Palazzo Leopoldo Dimora Storica & Spa

Torre a Cona Wine Estate

Torre a Cona Wine Estate
Rignano sull'Arno
HK$2,916
HK$3,235 total
includes taxes & fees
31 Aug - 1 Sept
Torre a Cona Wine Estate

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
HK$1,102
HK$1,248 total
includes taxes & fees
27 Aug - 28 Aug
Agriturismo San Sano

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
HK$979
HK$1,132 total
includes taxes & fees
23 Aug - 24 Aug
Hotel Palazzo San niccolò & Spa
View all properties

4-star hotels with pools in Chianti Region

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
HK$1,075
HK$1,237 total
includes taxes & fees
26 Aug - 27 Aug
Belvedere di San Leonino

Palagina la Dimora

Palagina la Dimora
Figline e Incisa Valdarno
HK$518
HK$588 total
includes taxes & fees
1 Sept - 2 Sept
Palagina la Dimora

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
HK$1,084
HK$1,247 total
includes taxes & fees
27 Aug - 28 Aug
Palazzo Leopoldo Dimora Storica & Spa

Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
HK$1,512
HK$1,941 total
includes taxes & fees
21 Aug - 22 Aug
Relais Vignale & Spa

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
HK$979
HK$1,132 total
includes taxes & fees
23 Aug - 24 Aug
Hotel Palazzo San niccolò & Spa

Villa Le Barone

Villa Le Barone
Greve in Chianti
HK$1,721
HK$1,947 total
includes taxes & fees
31 Aug - 1 Sept
Villa Le Barone

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
HK$1,732
HK$1,959 total
includes taxes & fees
23 Aug - 24 Aug
Palazzo Squarcialupi

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
HK$1,207
HK$1,363 total
includes taxes & fees
23 Aug - 24 Aug
Villa Casagrande Resort & SPA

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
HK$1,408
HK$1,603 total
includes taxes & fees
25 Aug - 26 Aug
Villa I Barronci Resort & Spa

Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
HK$1,851
HK$2,090 total
includes taxes & fees
26 Aug - 27 Aug
Hotel Villa Campomaggio
View all properties

5-star hotels with pools in Chianti Region

Borgo Vescine

Borgo Vescine
Radda in Chianti
HK$5,020
HK$5,594 total
includes taxes & fees
13 Sept - 14 Sept
Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
HK$3,110
HK$3,511 total
includes taxes & fees
16 Aug - 17 Aug
Castello di Spaltenna- Small Luxury Hotels of the World

Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
HK$3,077
HK$3,439 total
includes taxes & fees
20 Aug - 21 Aug
Chapter Chianti, a Member of Design Hotels

Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
HK$4,702
HK$5,245 total
includes taxes & fees
17 Aug - 18 Aug
Pieve Aldina - Relais & Châteaux

The Club House

The Club House
Castelnuovo Berardenga
HK$6,367
HK$7,094 total
includes taxes & fees
8 Sept - 9 Sept
The Club House

Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
HK$4,876
HK$5,455 total
includes taxes & fees
23 Aug - 24 Aug
Hotel Le Fontanelle

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
HK$4,008
HK$4,499 total
includes taxes & fees
26 Aug - 27 Aug
Borgo Scopeto Wine & Country Relais

Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
HK$5,020
HK$5,613 total
includes taxes & fees
18 Aug - 19 Aug
Borgo San Felice Resort

COMO Castello Del Nero

COMO Castello Del Nero
Barberino Tavarnelle
HK$6,845
HK$7,602 total
includes taxes & fees
21 Aug - 22 Aug
COMO Castello Del Nero

LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
HK$1,115
HK$1,281 total
includes taxes & fees
7 Sept - 8 Sept
LHP Certaldo Resort
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.
View all properties

Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"
C 3-night trip
Posted 17 hours ago
Villa Casagrande Resort & SPA
Villa San Filippo

Villa San Filippo

10/10 Excellent
"The location and views at this property cannot be beat. The pools were wonderful and overall it was a family friendly property. We traveled with 3 young children."
Kevin 4-night trip
Posted 2 days ago
Villa San Filippo
Belvedere di San Leonino

Belvedere di San Leonino

10/10 Excellent
"The most beautiful and breathtaking place to stay. The staff were lovely, the rooms were quiet, the views were exceptional. The breakfast was perfect. Idyllic!"
Jess 3-night trip
Posted 3 days ago
Belvedere di San Leonino
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent
"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."
Katie 5-night trip
Posted 8 days ago
Hu Norcenni Girasole Village
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 10 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Great staff!"
Philip 1-night trip
Posted 2 months ago
COMO Castello Del Nero

Explore a world of travel with Expedia