Hotels with Pool & Resorts in Montechiaro from AU$168

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Montechiaro Hotels with Pool

Our top choices for Montechiaro hotels with a pool

Exterior
Capanna Suites

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (131)
"Absolutely amazing resort with amazing staff and service. Great food and beautiful spa experience. Highly reccommend anyone going to Tuscany to book here - you will not be disappointed ! "
Canada
Megan
Capanna Suites
Outdoor pool, pool loungers
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is AU$196
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo di Pietrafitta Relais
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool loungers
Borgo Grondaie

Borgo Grondaie

Borgo Grondaie
3.0 star property
Siena
9.6 out of 10, Exceptional, (440)
"A hidden gem overlooking the city set in stunning grounds"
United Kingdom
Philip
Borgo Grondaie
Seasonal outdoor pool
Four Points by Sheraton Siena

Four Points by Sheraton Siena

Four Points by Sheraton Siena
4.0 star property
Scacciapensieri
8.8 out of 10, Excellent, (579)
"Comfortable rooms, excellent breakfast, lovely pool, and service!"
United States
Anonymous traveller
The price is AU$210
includes taxes & fees
16 Dec - 17 Dec
Four Points by Sheraton Siena
Seasonal outdoor pool, pool umbrellas, pool loungers
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel
4.0 star property
Camollia
8.4 out of 10, Very good, (5)
"Unique and cozy prot"
United States
Kristine
The price is AU$233
includes taxes & fees
21 Dec - 22 Dec
Villa Ermellina Siena, a Tribute Portfolio Hotel
Indoor pool, seasonal outdoor pool, pool loungers
Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (176)
"Ideal country setting"
Canada
Dee
The price is AU$186
includes taxes & fees
21 Dec - 22 Dec
Hotel Palazzo San niccolò & Spa
Outdoor pool, pool loungers
Molino di Foci

Molino di Foci

Molino di Foci
1.0 star property
San Gimignano
9.4 out of 10, Exceptional, (47)
"Breakfast was fresh and beautifully presented in the atrium with a view of the Tuscan landscape. "
Canada
Diego
Molino di Foci
Seasonal outdoor pool, pool loungers
Castello di Meleto

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (90)
"This Castle is AMAZING! Agatha and Victor so kind. I highly recommend this place. Wines are extremely wonderful. We really enjoy the staying."
United States
Karem
Castello di Meleto
Indoor pool, outdoor pool, pool loungers
Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (275)
"We loved it was easy to get to wineries or small towns we wanted to visit"
United States
Carol
The price is AU$168
includes taxes & fees
12 Jan - 13 Jan 2026
Palazzo Leopoldo Dimora Storica & Spa
Seasonal outdoor pool
Castello di Bossi

Castello di Bossi

Castello di Bossi
2.0 star property
Castelnuovo Berardenga
7.8 out of 10, Good, (8)
"The location is great if you get to the hotel in a car. "
Mexico
CESAR JAVIER
The price is AU$286
includes taxes & fees
19 Dec - 20 Dec
Castello di Bossi
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 Montechiaro Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Excellent hotel, very helpful staff, highly recommended "
Vikram 3-night trip
Posted 8 days ago
Hotel Athena

Frequently asked questions

What are some accommodation options with pools in Montechiaro?
Hotel Athena: Offers a full-service spa, an outdoor pool and a sauna. Villa La Borghetta Resort: Provides free self parking, a seasonal outdoor pool and complimentary bicycles. Borgo Grondaie: Features a children's pool, a seasonal outdoor pool and a rooftop terrace. Grand Hotel Continental Siena – Starhotels Collezione: Offers an indoor pool, an outdoor pool and 2 restaurants. Palazzo Ravizza: Features 2 restaurants, 2 outdoor swimming pools and a full-service spa.
What is there to see and do in Montechiaro?
The picturesque settings of Chianti Sculpture Park and Terme Antica Querciolaia showcase the area's natural beauty. During your stay, visit sights such as Porta Romana, San Martino and Siena State Archives.
When is the best time to book a hotel with a pool in Montechiaro?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Montechiaro in the warmest months of August, July or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 6°C.