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Our top choices for Montegrossi hotels

Gazebo
Hotel Villa San Giorgio

Hotel Villa San Giorgio

Hotel Villa San Giorgio
3.0 star property
Poggibonsi
9.0 out of 10, Wonderful, (105)
Immerse in Poggibonsi's charm at this welcoming hotel featuring poolside dining at Villa Aurora restaurant. Enjoy the spa pool and children's pool after exploring nearby Castello di Monsanto. Just a 12-minute drive from the train station for Tuscan adventures.
"Loved the breakfast amazing !!! Such a beautiful place woujd love to go in summer and lay by the pool "
Australia
Kylie
The price is NZ$128
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Villa San Giorgio
Exterior
Hotel Albergo Italia

Hotel Albergo Italia

Hotel Albergo Italia
2.0 star property
Poggibonsi
8.4 out of 10, Very good, (46)
Built in 1880, this Poggibonsi accommodation sits just 3 minutes from the train station. Explore nearby Fountain of Fate and Archeodromo attractions, then unwind with drinks at the cosy bar after your adventures.
"When I arrived the hotel was closed. I have had to sleep in the car"
United States
Martin
Hotel Albergo Italia
Seasonal outdoor pool, open 7 AM to 8:30 PM, pool umbrellas
Villa San Lucchese

Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (336)
Escape to this historic family-friendly hotel offering free breakfast and parking. Enjoy the seasonal outdoor pool and tennis courts, then unwind at the bar. Conveniently located near San Lucchese Convent and local Tuscan villages with train station access.
"Beautiful place Great service "
United States
patricia
Villa San Lucchese
Front of property – evening/night
Hotel Toscana Ambassador

Hotel Toscana Ambassador

Hotel Toscana Ambassador
4.0 star property
Poggibonsi
8.2 out of 10, Very good, (317)
This business-friendly hotel offers 24-hour room service with easy access to Poggibonsi-San Gimignano Station. Unwind at the bar or coffee shop after exploring nearby attractions like Archeodromo di Poggibonsi and Poggio Imperiale Fortress.
"Wonderful breakfast. Good location!"
Canada
Karen
The price is NZ$129
includes taxes & fees
2 Jan - 3 Jan 2026
Hotel Toscana Ambassador
View from room
Hotel Ristorante Alcide

Hotel Ristorante Alcide

Hotel Ristorante Alcide
4.0 star property
Poggibonsi
8.0 out of 10, Very good, (479)
Savour regional specialities at Ristorante Alcide, just an 11-minute walk from Poggibonsi-San Gimignano Station. This hotel offers a welcoming bar, terrace, and room service, with Archeodromo di Poggibonsi and Fountain of Fate nearby.
"I highly recommended "
Canada
George
The price is NZ$94
includes taxes & fees
18 Jan - 19 Jan 2026
Hotel Ristorante Alcide
Restaurant
Palazzo Tiglio - A Small Luxury Hotels of the World

Palazzo Tiglio - A Small Luxury Hotels of the World

Palazzo Tiglio - A Small Luxury Hotels of the World
Bucine
10.0 out of 10, Exceptional, (3)
Set in Bucine, this luxurious retreat offers a refreshing outdoor pool and peaceful garden terrace. Near historic Civitella Longobard Castle, guests enjoy complimentary WiFi and parking while exploring Tuscan treasures, with a café and lounge for relaxation.
"We found it to be a charming, immaculate, upscale retreat with a hilltop view of the beautiful countryside. We were given personalized attention and many unexpected fine touches, like fresh fruit in the room. Highly recommend."
United States
David
Palazzo Tiglio - A Small Luxury Hotels of the World
Exterior detail
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
Enchanting affittacamere featuring a seasonal outdoor pool, relaxing massage services, and convenient bar. Located near Monastary of Sorelle Clarisse and Antinori nel Chianti Classico, with complimentary breakfast, WiFi, and parking for a perfect Italian countryside retreat.
"Great people, great location great service"
Canada
James
The price is NZ$270
includes taxes & fees
13 Jan - 14 Jan 2026
Villa il Fedino
Exterior
Relais Poggio Borgoni

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (58)
Sip local wines at this charming countryside retreat between Florence and Chianti. The seasonal outdoor pool, spa pool, and Osteria del Poggio restaurant create a relaxing Italian escape. Free breakfast, WiFi and parking complement the attentive service.
"Very personal, kind & sympathatic Staff. The Place is gorgeous."
Switzerland
Nils
The price is NZ$225
includes taxes & fees
11 Jan - 12 Jan 2026
Relais Poggio Borgoni
Deluxe Apartment, 1 Bedroom
Delta Hotel

Delta Hotel

Delta Hotel
3.0 star property
Montevarchi
8.4 out of 10, Very good, (159)
This business-friendly hotel is just a 5-minute walk from Montevarchi-Terranuova Station. Travellers enjoy the fitness centre, coffee shop, and bar after exploring nearby Il Cassero. Free WiFi and parking enhance the convenient Tuscan stay.
"Very clean and staff were lovely"
United Kingdom
Diana
The price is NZ$309
includes taxes & fees
30 Jan - 31 Jan 2026
Delta Hotel
Outdoor pool, pool umbrellas, pool loungers
Le Lappe

Le Lappe

Le Lappe
Cavriglia
9.6 out of 10, Exceptional, (32)
Immerse yourself in Cavriglia's charm at this countryside retreat featuring an outdoor pool, spa pool, and rejuvenating sports massages. Savour Italian specialities at Giardino d'Inverno restaurant before exploring nearby Le Miccine attractions with convenient free parking and WiFi.
"Beautiful property in countryside Tuscany region ideal to stay for 2-7 days."
Canada
shrirang
Le Lappe
Property entrance
Hotel Valdarno

Hotel Valdarno

Hotel Valdarno
4.0 star property
Montevarchi
8.8 out of 10, Excellent, (216)
Unwind at this business-friendly Montevarchi hotel, just an 11-minute walk from the station. Enjoy complimentary breakfast, free WiFi, and 24-hour room service while exploring nearby Il Cassero and Accademia Valdarnese del Poggio Library.
"The property was well kept by staff. It was clean and the breakfast every morning was fantastic "
United States
Robert
Hotel Valdarno
Exterior
Castello di Leonina Relais

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (121)
Lose yourself in the Italian countryside at this historic relais. Unwind with deep-tissue massages and Ayurvedic treatments after exploring nearby Siena. The outdoor pool, spa pool, and Italian cuisine at Il Balcone di Leonina complete your authentic escape.
"Perfectb Quiet and very relaxing stay. Breakfast was very tasty and the view was absolutely spectacular "
United Kingdom
Mayara
Castello di Leonina Relais
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (335)
Immerse yourself in historic Siena from this convenient apartment, just a short drive from Piazza del Campo. The comfortable space offers a kitchenette, laundry facilities, and free WiFi, with Santa Maria della Scala nearby.
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is NZ$132
includes taxes & fees
30 Jan - 31 Jan 2026
ApartHotel Anghel
Couples treatment room(s), Turkish bath/hammam, body treatments
Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
5.0 star property
Castelnuovo Berardenga
8.8 out of 10, Excellent, (144)
Surrounded by Tuscan countryside, this elegant hotel offers two restaurants and a rejuvenating spa with thalassotherapy. Golf lovers can play adjacent courses while enjoying free breakfast and parking. Villa a Sesta Polo Club is nearby.
"Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back"
Canada
John
The price is NZ$1,451
includes taxes & fees
31 Dec - 1 Jan 2026
Castel Monastero - The Leading Hotels of the World
Front of property
Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
4.0 star property
Siena
9.8 out of 10, Exceptional, (186)
Discover serene luxury adjacent to a golf course in Siena, where an outdoor pool and tennis courts await. After activities, enjoy the bar or café. Located near Porta Romana with free breakfast, WiFi, and parking.
"The best in Siena."
Canada
David
The price is NZ$1,073
includes taxes & fees
1 Jan - 2 Jan 2026
Hotel Certosa Di Maggiano
Bar (on property)
Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
3.0 star property
Colle di Val d'Elsa
8.4 out of 10, Very good, (203)
Immerse in Tuscan charm at this hotel featuring a restaurant serving local cuisine for lunch and dinner. Near Museo del Cristallo and Piazza Arnolfo di Cambio, with convenient amenities like free breakfast, WiFi, and room service. Unwind at the bar or terrace.
"The staff was very welcoming. Lovely quiet place. Close to a lot of good restaurants. "
Canada
Sheila
Hotel La Vecchia Cartiera
Exterior
Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo
San Gimignano
9.6 out of 10, Exceptional, (54)
"Great boutique hotel in the middle of Tuscany. Wonderful views. The staff was very friendly and accommodating. We really loved the complimentary wine tasting at their nearby winery! We only wish their rooftop deck would’ve been open for even better views. The hotel and winery are family owned and it’s very clear that they value every guest!"
United States
Necola
Hotel Torciano Vecchio Asilo
Lounge
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)
Steps from Siena Station, this hotel offers Italian cuisine at IL PALIO restaurant and a refreshing seasonal outdoor pool. Free breakfast, WiFi, and parking enhance your stay near Palasport Mens Sana and Siena Stadium.
"Comfortable rooms, excellent breakfast, lovely pool, and service!"
United States
Anonymous traveller
The price is NZ$258
includes taxes & fees
8 Jan - 9 Jan 2026
Four Points by Sheraton Siena
Minibar, desk, iron/ironing board, free WiFi
Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri
Siena City Centre
8.0 out of 10, Very good, (89)
Just 14 minutes from Siena Station, this charming guesthouse offers easy access to Porta Camollia and Museo dell'Acqua. Enjoy hiking trails, mountain biking, free WiFi, and convenient room service while exploring the historic city centre.
"Nice and easy checking friendly staff "
United States
Jose
Relais La Corte Dei Cavalieri
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
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"The staff were exceptionally friendly and welcoming, making us feel comfortable from the moment we arrived. The breakfast was outstanding, with a great variety of fresh and high-quality options to choose from. Everything was well organised and very clean. We would happily stay here again and highly recommend this hotel."
Adam 2-night trip
Posted 5 days ago
Grand Hotel Continental Siena – Starhotels Collezione

More cheap accommodation in Montegrossi

Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
The price is NZ$163 per night from 29 Jan to 30 Jan
NZ$163
29 Jan - 30 Jan 2026
includes taxes & fees
7.8/10 Good! (389 reviews)

Frequently asked questions

Where is the best place to stay in Montegrossi?
Located 13.3 mi (21.3 km) from the heart of Montegrossi, Hotel Athena is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Borgo Grondaie and Villa La Borghetta Resort. See all available top hotels, or vacation rentals in Montegrossi.
What are some of the best holiday rentals that Montegrossi has to offer?
Borgo Argiano: This holiday home rental outside of Montegrossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library. See all vacation rentals in Montegrossi.
If I need to cancel my hotel reservation in Montegrossi, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Montegrossi.
What are some hotels with pools in Montegrossi?
Castello di Spaltenna- Small Luxury Hotels of the World: Offers an indoor pool, an outdoor pool and 2 restaurants. Hotel Borgo di Cortefreda Relais and Four Points by Sheraton Siena are two additional hotels that feature an on-site pool. View all hotels with pools in Montegrossi.
How is it to stay in Montegrossi?
Visitors to Montegrossi will definitely find plenty to explore and enjoy. In Montegrossi, there are 4 hotels and other accommodation options to choose from. Find out more about Montegrossi.
What are the top places to visit in Montegrossi?
Places to visit in the wider area include Badia a Coltibuono, Meleto Castle and Cantalici Winery. You'll also find Castello di Albola and Castello di Radda Winery in the area. Take a look at what more there is to see and do in Expedia's Montegrossi guide.
What's the seasonal weather like in Montegrossi?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Montegrossi is 946 mm.

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