Hotels with Swimming Pool in Montegrossi, Gaiole in Chianti

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Check availability on Montegrossi Hotels with Swimming Pool

Top Montegrossi Hotels with Swimming Pool

Outdoor pool, sun 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 P6,674
P7,616 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo di Pietrafitta Relais
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 P5,614
P6,587 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel Borgo di Cortefreda Relais
Seasonal outdoor pool
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 P5,424
P10,975 total
includes taxes & fees
Dec 12 - Dec 13
Castello di Bossi
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, sun 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, open 9:00 AM to 7:00 PM, sun 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 P8,450
P9,295 total
includes taxes & fees
Dec 14 - Dec 15
Villa Cassia di Baccano
Seasonal outdoor pool, pool umbrellas, sun loungers
Agriturismo Montemagni di Sopra

Agriturismo Montemagni di Sopra

Greve in Chianti
9.0 out of 10, Wonderful, (8)
"The hostess is very accommodating and sweet. The beds were incredibly comfy and shower was spacious. A very lovely and peaceful stay! "
United States
Rachel
The price is P5,614
P6,450 total
includes taxes & fees
Dec 10 - Dec 11
Agriturismo Montemagni di Sopra
Outdoor pool, sun 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
Indoor pool, seasonal outdoor pool, sun loungers
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 P6,408
P7,461 total
includes taxes & fees
Dec 23 - Dec 24
Hotel Palazzo San niccolò & Spa
Exterior
Relais Poggio Borgoni

Relais Poggio Borgoni

San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (57)
"Very personal, kind & sympathatic Staff. The Place is gorgeous."
Switzerland
Nils
The price is P6,043
P6,922 total
includes taxes & fees
Dec 11 - Dec 12
Relais Poggio Borgoni
Seasonal outdoor pool
Sangallo Park Hotel

Sangallo Park Hotel

3.0 star property
Vico Alto
9.0 out of 10, Wonderful, (594)
"Spacious accommodation and everything works! Great parking, pool and gardens with views across the valley to nearby Siena. Very nice breakfast and lovely staff. Excellent value too!"
United Kingdom
David
The price is P5,053
P5,764 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sangallo Park Hotel
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
"The hotel is in an excellent location. The room is extremely comfortable and has a beautiful view. All the staff are super friendly, helpful, and always smiling. The breakfast is varied, delicious, and amazing. I would definitely stay here again."
Natalia 1-night trip
Posted 4 days ago
Hotel Athena

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 like Borgo di Vescine - Tenute di Castelvecchi and Siena Circuit. During your stay, check out 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 that has an outdoor pool if you will be visiting Montegrossi in the warmest months of August, July, or June when the average temp is 72°F. Lodging with 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 44°F.