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Our top choices for Montegrossi hotels

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
Soak in Tuscany from the rooftop terrace at this charming Castelnuovo Berardenga retreat. The on-site restaurant serves Italian cuisine throughout the day, while the garden setting creates a peaceful atmosphere. Terra di Seta and free perks like WiFi, parking, and breakfast add value.

"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is ¥12,997
¥15,036 total
includes taxes & fees
Dec 21 - Dec 22
La Certosa di Pontignano

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1002)
This business-friendly hotel offers a scenic rooftop terrace, free WiFi, and complimentary parking. Guests praise the delicious breakfast and attentive staff. Sample local cuisine at Mangia restaurant, relax at the bar, or visit nearby National Museum of Archaeology.

"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is ¥13,701
¥15,618 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hotel Athena

Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1000)
Charming hotel with a restaurant and garden terrace near Stadio Artemio Franchi. Enjoy the complimentary breakfast before exploring nearby Fontebranda. The attentive staff ensures a comfortable stay while room service and free WiFi add convenience.

"Lovely staff and great location with a quiet, comfortable room."
United States
Katherine
The price is ¥12,494
¥14,297 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hotel Chiusarelli

Hotel Italia

Hotel Italia
3.0 star property
Camollia
9.2 out of 10, Wonderful, (1000)
Experience Siena from this convenient hotel near the train station. Enjoy hiking and mountain biking trails nearby, plus visit Porta Camollia and Siena Stadium. Relax at the bar or on the terrace after exploring. Guests consistently praise the helpful staff and morning breakfast.

"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is ¥10,300
¥11,877 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Hotel Italia

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (33)
Immersed in wine country near Monteriggioni Castle, this charming hotel offers traditional regional cuisine and comfortable accommodations. Enjoy free breakfast, WiFi, and parking while exploring nearby Lilliano Estate Winery.

"Very nice staff and very nice place to stay."
United Kingdom
Ryan
The price is ¥15,978
¥18,306 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hotel Ristorante La Dama nella Vigna

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.2 out of 10, Very Good, (51)
Set in a convenient location near historic attractions, this hotel offers a restaurant and bar/lounge where guests can relax. Free WiFi and parking enhance the stay, while Basilica di Santa Maria dei Servi is easily accessible.

"Nice place to stay. Fairly close to the medieval area. No need to worry about any ZTL issue. "
United States
joseph
Palace Hotel Due Ponti

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (749)
Located near Pinacoteca Nazionale, this Siena hotel offers free WiFi, room service, and a tranquil terrace garden. Just minutes from the National Museum of Archaeology, guests rave about the delicious breakfast and attentive staff.

"We enjoyed our stay here."
United States
LAURIA
The price is ¥16,123
¥18,282 total
includes taxes & fees
Dec 21 - Dec 22
Palazzo Ravizza

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 traveler
The price is ¥19,496
¥22,000 total
includes taxes & fees
Dec 23 - Dec 24
Four Points by Sheraton Siena

Piccolo Hotel Etruria

Piccolo Hotel Etruria
2.0 star property
Siena City Centre
8.0 out of 10, Very Good, (389)
"Great location right in the heart of Siena. "
United Kingdom
Sian
The price is ¥12,739
¥14,560 total
includes taxes & fees
Dec 23 - Dec 24
Piccolo Hotel Etruria

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 ¥18,413
¥20,809 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Villa Ermellina Siena, a Tribute Portfolio Hotel

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (478)
Experience Tuscan charm at this hillside hotel with outdoor pool and poolside bar. Enjoy local cuisine at Ristorante Cortefreda after a day of massages at the spa. Near Abbey of Passignano and Casa Sola Winery with helpful staff to enhance your stay.

"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is ¥13,287
¥15,723 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel Borgo di Cortefreda Relais

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (57)
Sip local wines at this charming countryside retreat between Florence and Chianti. The seasonal outdoor pool, hot tub, 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 ¥16,106
¥18,456 total
includes taxes & fees
Dec 21 - Dec 22
Relais Poggio Borgoni

Hotel Minerva

Hotel Minerva
3.0 star property
Siena City Centre
8.2 out of 10, Very Good, (1000)
Set in charming Siena, this hotel offers complimentary cooked-to-order breakfast and WiFi. Explore nearby attractions or relax in the garden after hiking local trails. The bar and room service enhance your stay, with Siena Station just a 15-minute walk away.

"Helpful staff and overall vibe. "
United States
Robert
The price is ¥12,442
¥14,240 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Minerva

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (120)
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, hot tub, 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
The price is ¥25,167
¥28,778 total
includes taxes & fees
Dec 28 - Dec 29
Castello di Leonina Relais

Il Chiostro del Carmine

Il Chiostro del Carmine
Siena Historical Center
8.6 out of 10, Excellent, (870)
Experience the heart of Siena at this B&B with free daily buffet breakfast and WiFi. Guests praise the helpful staff, and you'll find room service available. Nearby attractions include the Natural History Museum and Pinacoteca Nazionale.

"Terrific place to stay. Breakfast was great, staff were friendly, and the view we had was stunning. Lots of room Old monastery was very interesting. "
Canada
John
Il Chiostro del Carmine

NH Siena

NH Siena
4.0 star property
Siena Historical Center
8.2 out of 10, Very Good, (1000)
Immerse yourself in historic Siena at this centrally located hotel, just a 10-minute walk from iconic Piazza del Campo. Enjoy local cuisine at Al Rastrello restaurant, maintain your routine in the fitness center, and receive personalized assistance from the highly praised staff.

"The staff were excellent. They called taxis and were very courteous, helpful, attentive and professional. I ate dinner at the hotel restaurant and it was only fair."
United States
William
The price is ¥17,085
¥19,341 total
includes taxes & fees
Jan 18 - Jan 19, 2026
NH Siena

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
Set adjacent to a golf course with easy access to Fontebranda and Piccolomini Library. This hotel offers refrigerators and microwaves in rooms, plus free WiFi and room service. Guests love the helpful staff and clean accommodations.

"A great location!"
Canada
Cheryl
The price is ¥22,036
¥24,979 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siena Vip

Borgo Grondaie

Borgo Grondaie
3.0 star property
Siena
9.6 out of 10, Exceptional, (440)
"A hidden gem overlooking the city set in stunning grounds"
United Kingdom
Philip
Borgo Grondaie

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (177)
Surrounded by Chianti vineyards, this spa hotel offers indulgent treatments, 2 restaurants, and both indoor and outdoor pools. Explore nearby Castello di Radda Winery or unwind at the poolside bar after a day in picturesque Tuscan countryside.

"Ideal country setting"
Canada
Dee
The price is ¥17,870
¥20,752 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hotel Palazzo San niccolò & Spa

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (90)
Immerse yourself in authentic Tuscany at this historic castle estate. Enjoy wine tastings at the on-site winery, cool off in the seasonal outdoor pool, and dine at La Fornace di Meleto restaurant. Free WiFi and parking complement the beautiful garden and terrace settings.

"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
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

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Frequently asked questions

Where is the best place for a 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 traveler data. Two other choices 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's the top vacation rental in Montegrossi?
Borgo Argiano: This vacation home rental outside of Montegrossi is located on a river and has a balcony, a terrace, and a barbecue grill 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 vacation 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 bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Montegrossi.
Where can I learn more about changing or cancelling my trip to Montegrossi?
To find more details about rescheduling or cancelling your trip to Montegrossi, head over to our customer service page.
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 onsite pool. View all hotels with pools in Montegrossi.
What's it like to stay in Montegrossi?
Visitors to Montegrossi are sure to find plenty to explore and enjoy. In Montegrossi, there are 4 hotels and other accommodations 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, Le Miccine, and Meleto Castle. You'll also find Cantalici Winery and Castello di Albola in the area. Check out what more 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 temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Montegrossi is 37 inches.

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