Montalcino Hotels with Swimming Pool

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 Montalcino Hotels with Swimming Pools

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Montalcino Hotels with Swimming Pools

Exterior
Capanna Suites

Capanna Suites

Montalcino
9.8 out of 10, Exceptional, (130)
"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
Exterior
Mastrojanni Relais

Mastrojanni Relais

Montalcino
10.0 out of 10, Exceptional, (61)
"This is the most magical and beautiful property in Tuscany with amazing food and service. The guests talk about how they come back every year to this resort The views from the pool are the best in this area. "
United States
Laura
The price is RM1,552
RM1,755 total
includes taxes & fees
21 Dec - 22 Dec
Mastrojanni Relais
Seasonal outdoor pool, open 9:30 AM to 7:30 PM, pool umbrellas
Le Ragnaie

Le Ragnaie

Montalcino
9.2 out of 10, Wonderful, (323)
"Great place to stay the staff was super friendly and very close to Monalcino. Good wine everywhere. The scenery was so beautiful! "
United States
Douglas
Le Ragnaie
Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas
Cordella in Montalcino Wine Resort

Cordella in Montalcino Wine Resort

Montalcino
8.4 out of 10, Very good, (21)
"One of the best places we stayed for one night , the host (owner and chef) was very friendly and the food he cooked was amazing - one of the best meals we had in the 3 weeks we stayed in Italy. Getting there by car was convenient but no easy to find. Once you are there the place is amazing and the food just great!"
Canada
Edgardo
The price is RM196
RM235 total
includes taxes & fees
8 Dec - 9 Dec
Cordella in Montalcino Wine Resort
Exterior
Il Burellino Wine & Resort

Il Burellino Wine & Resort

Montalcino
10.0 out of 10, Exceptional, (76)
"Absolutely beautiful place."
United States
Stephanie
The price is RM674
RM780 total
includes taxes & fees
9 Dec - 10 Dec
Il Burellino Wine & Resort
Outdoor pool, pool loungers
Hotel Dei Capitani

Hotel Dei Capitani

3.0 star property
Montalcino
8.8 out of 10, Excellent, (416)
"Most beautiful view from hotel room"
United States
Diane
Hotel Dei Capitani
View from property
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5.0 star property
Montalcino
9.0 out of 10, Wonderful, (339)
"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."
United States
Jose
Castello di Velona Resort Thermal SPA & Winery
Outdoor pool
Antico Brunello

Antico Brunello

Montalcino
The price is RM31,657
RM34,871 total
includes taxes & fees
3 Jan - 4 Jan 2026
Antico Brunello
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 Montalcino Hotel Reviews

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"La habitación muy amplia, teníamos armario vestidor, sala, habitación amplia y un gran baño. Excelente la atención del personal. El lugar mágico maravilloso de epoca"
ROGERIO 5-night trip
Posted 4 days ago
Hotel Certosa Di Maggiano

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Montalcino?
If lounging by a pool is your idea of a great holiday, you may want to explore historic Montalcino, which has 16 places to stay with pools. While you're visiting, you can explore sights such as Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi, and then kick back and relax poolside at one of the accommodation options in Montalcino that guests like for their pools.
What are some hotels with pools in Montalcino?
Rosewood Castiglion del Bosco: Features 2 restaurants, 2 outdoor swimming pools and a full-service spa. SI Montalcino Hotel: Offers a snack bar/deli, a seasonal outdoor pool and buffet. Cordella in Montalcino Wine Resort: Provides a rooftop terrace, a seasonal outdoor pool and free self parking. Le Ragnaie: Features buffet, a seasonal outdoor pool and free self parking.
How many hotels with pools will I find in Montalcino?
Expedia's 16 hotels in Montalcino give you a great choice for your poolside getaway.
What is there to see and do in Montalcino?
The picturesque setting of Val di Merse and Val di Chiana showcase the area's natural beauty. During your stay, visit sights such as Fortress of Montalcino, Tenuta Greppo Franco Biondi Santi and Abbazia di Sant'Antimo. The countryside, wineries and historic landmarks are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Montalcino?
You may want to think about a place to stay that offers an outdoor pool if you'll be visiting Montalcino in the warmest months of August, July or June, when the average temperature is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or December, when the average temp is 5°C.