Hotels in Montegrossi

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Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (92 reviews)
Immerse yourself in Tuscan charm at this family-friendly hotel featuring its own winery. Enjoy complimentary breakfast before exploring nearby Chianti Sculpture Park and Meleto Castle. Return for a refreshing dip in the seasonal pool or unwind at the bar.
The price is $108
$124 total
includes taxes & fees
Jun 5 - Jun 6
Agriturismo San Sano

Castello

Castello
3.0 star property
Sovicille
8.6 out of 10, Excellent, (73 reviews)
Immerse in the charm of this Tuscan hotel featuring regional dishes at Ai Girasoli restaurant. The property offers a welcoming bar, garden terrace, and 24-hour room service. Near Porta Tufi with free WiFi and parking, it's a short drive from Asciano Arbia Station.
The price is $88
$101 total
includes taxes & fees
Jun 5 - Jun 6
Castello

Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
4.0 star property
Arezzo
8.6 out of 10, Excellent, (157 reviews)
This Arezzo hotel features a full-service spa offering massages and facials. Enjoy drinks at the bar, snacks at the deli, or meals at the café. Located near Arezzo Equestrian Centre with free WiFi and parking for convenient exploration.
The price is $66
$79 total
includes taxes & fees
Jun 8 - Jun 9
Il Gentiluomo Hotel & SPA

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very Good, (60 reviews)
Immerse yourself in Siena's culture at this comfortable retreat, where complimentary breakfast fuels your adventures. Just minutes from Porta Romana and Basilica di Santa Maria dei Servi, with a restaurant and bar for evening relaxation and free WiFi and parking.
The price is $83
$97 total
includes taxes & fees
Jun 7 - Jun 8
Palace Hotel Due Ponti

Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (342 reviews)
Set in Poggibonsi near San Lucchese Convent, this family-friendly hotel offers a seasonal outdoor pool, tennis courts, and poolside bar. Just 6 minutes from the train station, it's perfectly positioned for exploring picturesque towns across Tuscany.
The price is $132
$152 total
includes taxes & fees
Jun 11 - Jun 12
Villa San Lucchese

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (538 reviews)
The price is $128
$150 total
includes taxes & fees
Jun 29 - Jun 30
La Certosa di Pontignano

Hotel Palazzo dei Priori

Hotel Palazzo dei Priori
4.0 star property
Siena
8.8 out of 10, Excellent, (418 reviews)
The price is $91
$116 total
includes taxes & fees
Jun 5 - Jun 6
Hotel Palazzo dei Priori

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (41 reviews)
Nestled in Monteriggioni, this countryside hotel offers free breakfast, WiFi, and parking. The onsite restaurant and bar provide authentic flavors after exploring nearby Monteriggioni Castle or Lilliano Estate Winery, just a short drive from Badesse Station.
The price is $123
$141 total
includes taxes & fees
Jun 14 - Jun 15
Hotel Ristorante La Dama nella Vigna

Hotel Palazzo Renieri - 3stelle S

Hotel Palazzo Renieri - 3stelle S
3.0 star property
Colle di Val d'Elsa
8.6 out of 10, Excellent, (87 reviews)
Located in Colle di Val d'Elsa, this welcoming hotel offers 2 restaurants including Portanova Hosteria Enotec serving Italian cuisine, plus a wine bar. Explore Art in Color and the Ranuccio Bianchi Bandinelli Archeological Museum nearby.
The price is $80
$91 total
includes taxes & fees
Jul 2 - Jul 3
Hotel Palazzo Renieri - 3stelle S

Hotel Casafrassi Wine Resort

Hotel Casafrassi Wine Resort
4.0 star property
Castellina in Chianti
8.2 out of 10, Very Good, (220 reviews)
Surrounded by beautiful countryside scenery, this Castellina in Chianti hotel offers Italian dining at Osteria di Casafrassi and a winery on-site. Enjoy free breakfast near Mazzei Winery, just 9 minutes from Monteriggioni Badesse Station.
The price is $51
$75 total
includes taxes & fees
Jun 5 - Jun 6
Hotel Casafrassi Wine Resort

Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio
3.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (204 reviews)
Escape to this Tuscan retreat with an inviting outdoor pool and poolside bar. Enjoy regional specialties at the hotel restaurant after exploring nearby Fashion Groove and The Mall Luxury Outlet. Free breakfast, WiFi, and parking complete your family-friendly stay.
The price is $90
$103 total
includes taxes & fees
Jun 19 - Jun 20
Hotel Tenuta Il Burchio

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.0 out of 10, Wonderful, (108 reviews)
Escape to this charming wine resort in Gaiole in Chianti with a rooftop terrace overlooking the countryside. Near Meleto Castle, this retreat offers tennis courts, an outdoor pool, and on-site winery. Enjoy free breakfast and parking.
The price is $239
$272 total
includes taxes & fees
Jun 23 - Jun 24
Castello di Tornano Wine Resort

Azienda agricola la camporena

Azienda agricola la camporena
Greve in Chianti
The price is $134
$152 total
includes taxes & fees
Jun 9 - Jun 10
Azienda agricola la camporena

Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (207 reviews)
Peaceful sanctuary near Alta Val d'Elsa River Park with a stunning rooftop terrace and outdoor pool. Enjoy drinks at the poolside bar or unwind in the quiet atmosphere after a free breakfast. Near Le Caldane Thermal Baths with easy parking.
The price is $171
$192 total
includes taxes & fees
Jun 21 - Jun 22
Villa Sabolini

Hotel Fattoria degli Usignoli

Hotel Fattoria degli Usignoli
4.0 star property
Reggello
8.2 out of 10, Very Good, (166 reviews)
In the scenic Tuscan countryside, this family-friendly hotel offers 2 outdoor pools, tennis courts, and a poolside bar. Explore nearby Masaccio Museum and Abbazia di Vallombrosa after enjoying lunch at the onsite restaurant. Free WiFi and parking complete your stay.
The price is $98
$116 total
includes taxes & fees
Jun 4 - Jun 5
Hotel Fattoria degli Usignoli

Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
4.0 star property
Monteriggioni
8.6 out of 10, Excellent, (346 reviews)
Immerse yourself in Monteriggioni's charm at this serene hotel near Monteriggioni Castle. Enjoy the outdoor pool with poolside bar, relax with spa treatments, and savor Italian cuisine at La Ducareccia restaurant while exploring medieval Tuscan treasures.
The price is $126
$147 total
includes taxes & fees
Jun 18 - Jun 19
Hotel Il Piccolo Castello

Delta Hotel

Delta Hotel
3.0 star property
Montevarchi
8.4 out of 10, Very Good, (164 reviews)
Discover this Montevarchi hotel just 5 minutes from the train station, offering free WiFi and parking. After a workout at the fitness center, unwind on the terrace or grab a bite at the café. Il Cassero and Accademia Valdarnese are nearby.
The price is $124
$136 total
includes taxes & fees
Jun 4 - Jun 5
Delta Hotel

Hotel Executive

Hotel Executive
4.0 star property
Scacciapensieri
8.4 out of 10, Very Good, (538 reviews)
Escape to this welcoming hotel near Siena's train station, featuring an on-site restaurant serving local flavors. Enjoy the garden, convenient bar/lounge, and helpful staff. Palasport Mens Sana and Siena Stadium are just minutes away, with free WiFi and parking for easy exploration.
The price is $106
$123 total
includes taxes & fees
Jul 3 - Jul 4
Hotel Executive

Precise House Montaperti Siena

Precise House Montaperti Siena
4.0 star property
Asciano
8.4 out of 10, Very Good, (611 reviews)
Panoramic vistas await at this Asciano hotel where an indoor pool, rooftop terrace, and spa massages refresh travel-weary bodies. Just minutes from Siena Circuit, enjoy free breakfast before exploring nearby attractions.
The price is $139
$159 total
includes taxes & fees
Jun 7 - Jun 8
Precise House Montaperti Siena

Park Hotel Chianti

Park Hotel Chianti
4.0 star property
Barberino Tavarnelle
9.0 out of 10, Wonderful, (262 reviews)
Surrounded by Chianti's rolling hills, this hotel offers a refreshing seasonal pool with poolside bar. Explore nearby Antinori vineyards and Abbey of Passignano using free bike rentals, then unwind at the lounge after a day of adventures.
The price is $129
$149 total
includes taxes & fees
Jun 29 - Jun 30
Park Hotel Chianti
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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Frequently asked questions

What hotels do travelers like in Montegrossi?
Can I book a refundable hotel in Montegrossi?
If you're looking for the flexibility to change your travel plans to Montegrossi, most properties offer refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Montegrossi be like during my trip?
August and July are typically the warmest months in Montegrossi when the average temp is 72°F. January and February are the coldest months when the average temperature is 44°F. November and October are the months with the most rain.
Why should I book my Montegrossi accommodation with Hotels.com?
There are plenty of reasons to book your Montegrossi travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.