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
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chianti Region hotels with a pool

1. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
  • Poolside bliss awaits at this Tuscan wine resort where medieval castle meets vineyard views.
HK$1,125
HK$1,309 total
includes taxes & fees
29 Oct - 30 Oct
Castello di Tornano Wine Resort

2. 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.
HK$1,496
HK$1,699 total
includes taxes & fees
25 Oct - 26 Oct
Hotel Villa Campomaggio

3. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
  • Refreshing infinity pool with breathtaking views awaits at this charming Tuscan farm stay with winery.
HK$1,351
HK$1,486 total
includes taxes & fees
29 Oct - 30 Oct
Castello Vicchiomaggio

4. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
HK$656
HK$758 total
includes taxes & fees
25 Oct - 26 Oct
Borgo di Pietrafitta Relais

5. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
  • Tuscan retreat offers sparkling outdoor pool with free cabanas, loungers, and refreshing poolside bar service.
HK$668
HK$807 total
includes taxes & fees
25 Oct - 26 Oct
Ultimo Mulino Wellness Country Hotel

6. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
HK$970
HK$1,120 total
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino

7. 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$1,280
HK$1,683 total
includes taxes & fees
26 Oct - 27 Oct
Relais Vignale & Spa

8. 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$724
HK$850 total
includes taxes & fees
29 Oct - 30 Oct
Villa I Barronci Resort & Spa

9. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
  • Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.
HK$2,332
HK$2,637 total
includes taxes & fees
28 Oct - 29 Oct
Dievole Wine Resort

10. La pietra del cabreo

La pietra del cabreo
Greve in Chianti
  • Dive into the seasonal outdoor pool with breathtaking views at this beautifully maintained rural bed & breakfast.
HK$1,606
HK$1,802 total
includes taxes & fees
30 Sept - 1 Oct
La pietra del cabreo
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$656
HK$758 total
includes taxes & fees
25 Oct - 26 Oct
Borgo di Pietrafitta Relais

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
HK$668
HK$807 total
includes taxes & fees
25 Oct - 26 Oct
Ultimo Mulino Wellness Country Hotel

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
HK$579
HK$673 total
includes taxes & fees
18 Oct - 19 Oct
Agriturismo San Sano

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
HK$1,125
HK$1,309 total
includes taxes & fees
29 Oct - 30 Oct
Castello di Tornano Wine Resort

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
HK$970
HK$1,120 total
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
HK$478
HK$580 total
includes taxes & fees
30 Sept - 1 Oct
Hotel Casafrassi

Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
HK$1,280
HK$1,683 total
includes taxes & fees
26 Oct - 27 Oct
Relais Vignale & Spa

Villa Barberino

Villa Barberino
Meleto
HK$1,110
HK$1,222 total
includes taxes & fees
26 Oct - 27 Oct
Villa Barberino

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
HK$724
HK$850 total
includes taxes & fees
29 Oct - 30 Oct
Villa I Barronci Resort & Spa

Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
HK$401
HK$451 total
includes taxes & fees
5 Oct - 6 Oct
Palagina la cascina
View all properties

4-star hotels with pools in Chianti Region

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
HK$668
HK$807 total
includes taxes & fees
25 Oct - 26 Oct
Ultimo Mulino Wellness Country Hotel

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
HK$724
HK$850 total
includes taxes & fees
29 Oct - 30 Oct
Villa I Barronci Resort & Spa

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
HK$970
HK$1,120 total
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino

Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
HK$1,280
HK$1,683 total
includes taxes & fees
26 Oct - 27 Oct
Relais Vignale & Spa

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
HK$478
HK$580 total
includes taxes & fees
30 Sept - 1 Oct
Hotel Casafrassi

Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
HK$1,496
HK$1,699 total
includes taxes & fees
25 Oct - 26 Oct
Hotel Villa Campomaggio

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
Tavarnelle Val di Pesa
HK$1,044
HK$1,202 total
includes taxes & fees
24 Oct - 25 Oct
Hotel Borgo di Cortefreda Relais

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
HK$1,092
HK$1,255 total
includes taxes & fees
15 Oct - 16 Oct
Villa Casalecchi Country Hotel

Park Hotel Chianti

Park Hotel Chianti
Tavarnelle Val di Pesa
HK$652
HK$771 total
includes taxes & fees
29 Oct - 30 Oct
Park Hotel Chianti

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
HK$1,452
HK$1,650 total
includes taxes & fees
25 Oct - 26 Oct
Palazzo Leopoldo Dimora Storica & Spa
View all properties

5-star hotels with pools in Chianti Region

Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
HK$2,141
HK$2,409 total
includes taxes & fees
6 Oct - 7 Oct
Chapter Chianti, a Member of Design Hotels

Borgo Vescine

Borgo Vescine
Radda in Chianti
HK$4,117
HK$4,600 total
includes taxes & fees
20 Oct - 21 Oct
Borgo Vescine

Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
HK$2,861
HK$3,219 total
includes taxes & fees
22 Oct - 23 Oct
Pieve Aldina - Relais & Châteaux

LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
HK$932
HK$1,079 total
includes taxes & fees
29 Oct - 30 Oct
LHP Certaldo Resort

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
HK$2,628
HK$2,979 total
includes taxes & fees
30 Oct - 31 Oct
Castello di Spaltenna- Small Luxury Hotels of the World

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
HK$4,205
HK$4,714 total
includes taxes & fees
20 Oct - 21 Oct
Borgo Scopeto Wine & Country Relais

Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
HK$4,368
HK$4,894 total
includes taxes & fees
14 Oct - 15 Oct
Hotel Le Fontanelle

Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
HK$5,677
HK$6,334 total
includes taxes & fees
25 Oct - 26 Oct
Borgo San Felice Resort

The Club House

The Club House
Castelnuovo Berardenga
HK$5,687
HK$6,345 total
includes taxes & fees
20 Oct - 21 Oct
The Club House

COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
HK$6,251
HK$6,948 total
includes taxes & fees
30 Oct - 31 Oct
COMO Castello Del Nero
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 I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"Excellent dinner, spacious rooms, pol and jacuzzi, and incredible views!"
Danny 1-night trip
Posted 1 day ago
Villa I Barronci Resort & Spa
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"In a convenient location."
MELISSA 2-night trip
Posted 1 day ago
Relais Vignale & Spa
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."
Tereza 2-night trip
Posted 2 days ago
Villa Le Barone
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent
"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."
Maya 4-night trip
Posted 2 days ago
Hu Norcenni Girasole Village
Villa Il Palagio

Villa Il Palagio

10/10 Excellent
"The check in went great and the property is amazingly managed, a beautiful villa in the hills of Tuscany. It felt magic just walking to it, I would absolutely recommend renting a car if you want to go into Florence often."
Max 8-night trip
Posted 6 days ago
Villa Il Palagio
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"Great hotel"
Dario 2-night trip
Posted 7 days ago
Hotel Villa Campomaggio
Park Hotel Chianti

Park Hotel Chianti

10/10 Excellent
"The staff are very helpful and kind."
Manuel 2-night trip
Posted 11 days ago
Park Hotel Chianti
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 12 days ago
Palagina la Dimora
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 3 weeks ago
COMO Castello Del Nero

Explore a world of travel with Expedia