Hotels with Pool & Resorts in Montegrossi 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 Montegrossi Hotels with Pool

Best Montegrossi Hotels with Pool

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (478)
"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is AU$168
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Borgo di Cortefreda Relais
Outdoor pool, pool loungers
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$195
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

3.0 star property
Siena
9.6 out of 10, Exceptional, (439)
"A hidden gem overlooking the city set in stunning grounds"
United Kingdom
Philip
Borgo Grondaie
Seasonal outdoor pool, pool loungers
Castello di Meleto

Castello di Meleto

Gaiole in Chianti
8.8 out of 10, Excellent, (89)
"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
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$221
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano
Seasonal outdoor pool
Four Points by Sheraton Siena

Four Points by Sheraton Siena

4.0 star property
Scacciapensieri
8.8 out of 10, Excellent, (577)
"Comfortable rooms, excellent breakfast, lovely pool, and service!"
United States
Anonymous traveller
The price is AU$209
includes taxes & fees
15 Dec - 16 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

4.0 star property
Camollia
8.4 out of 10, Very good, (5)
"Unique and cozy prot"
United States
Kristine
The price is AU$232
includes taxes & fees
21 Dec - 22 Dec
Villa Ermellina Siena, a Tribute Portfolio Hotel
Outdoor pool, pool loungers
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
Exterior
B&B Country House Poggio del Drago

B&B Country House Poggio del Drago

Civitella in Val di Chiana
9.8 out of 10, Exceptional, (57)
"Staff were friendly and helpful. Breakfast was just right - some fresh fruit would be nice to have. B&B was clean and tidy. Good signage so place was reasonably easy to find."
United States
Ludwig
B&B Country House Poggio del Drago
Seasonal outdoor pool
La Pensione di Vignamaggio

La Pensione di Vignamaggio

Panzano in Chianti
9.6 out of 10, Exceptional, (117)
"A beautiful location, fantastic view, close to wineries, little shops and local restaurants. "
Canada
Rob
La Pensione di Vignamaggio
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 Montegrossi Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"
Phil 1-night trip
Posted 5 days ago
Hotel Italia

Frequently asked questions

What are some hotels with pools in Montegrossi?
Hotel Athena: Offers a full-service spa, an outdoor pool and a sauna. Villa La Borghetta Resort: Offers a children's pool, a seasonal outdoor pool and a full-service spa. Grand Hotel Continental Siena – Starhotels Collezione: Offers an indoor pool, an outdoor pool and 2 restaurants. Palazzo Ravizza: Offers a seasonal outdoor pool, an indoor pool and 2 restaurants. Hotel Ristorante Alcide: Features a snack bar/deli, an outdoor pool and buffet.
What is there to see and do in Montegrossi?
Make a point to visit attractions such as Borgo di Vescine - Tenute di Castelvecchi and Siena Circuit. During your stay, visit sights such as Badia a Coltibuono, Le Miccine and Meleto Castle.
When is the best time to book a hotel with a pool in Montegrossi?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Montegrossi in the warmest months of August, July or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 6°C.