Hotels with Pool & Resorts in Montegrossi from NZ$184

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Check availability on Montegrossi Hotels with Pool

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Montegrossi hotels with a pool

Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (480)
"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is NZ$184
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

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is NZ$247
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo di Pietrafitta Relais
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers
Villa Cassia di Baccano

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 NZ$220
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano
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
9.0 out of 10, Wonderful, (7)
"Unique and cozy prot"
United States
Kristine
The price is NZ$228
includes taxes & fees
5 Jan - 6 Jan 2026
Villa Ermellina Siena, a Tribute Portfolio Hotel
Lunch, dinner served; Italian cuisine, pool views
Hotel Borgo San Luigi

Hotel Borgo San Luigi

Hotel Borgo San Luigi
4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (405)
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
United States
Allyson
Hotel Borgo San Luigi
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 NZ$246
includes taxes & fees
6 Jan - 7 Jan 2026
Four Points by Sheraton Siena
Seasonal outdoor pool, pool loungers
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is NZ$270
includes taxes & fees
13 Jan - 14 Jan 2026
Villa il Fedino
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)
"Excellent place to stay for a relaxing weekend and enjoy the view of Siena"
United States
Enrique
Borgo Grondaie
Exterior
B&B Country House Poggio del Drago

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
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 NZ$284
includes taxes & fees
6 Jan - 7 Jan 2026
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.
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Top Montegrossi Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Clean"
Young 1-night trip
Posted 6 days ago
Hotel Athena

Frequently asked questions

What are some hotels with pools in Montegrossi?
Hotel Athena: Offers free self parking, a seasonal outdoor pool and complimentary bicycles. Borgo Grondaie: Provides 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: Provides 2 restaurants, a seasonal outdoor pool and a full-service spa. Palazzo Ravizza: Offers a children's pool, a seasonal outdoor pool and a rooftop terrace.
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, Meleto Castle and Cantalici Winery.
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.