Find hotels in Montegrossi from Rp1.284.921

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Montegrossi hotels

Exterior
Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (83)
Immerse in Siena's medieval heart at this intimate guesthouse. Free WiFi and daily housekeeping complement comfortable rooms with cable TV. Museum of Torture and Palazzo Chigi-Saracini await nearby, with Siena Station just a 15-minute drive away.
"Beautiful area, very walkable! "
United States
Anita
Residenza d'Epoca Le Aquile
2 restaurants, breakfast, lunch, dinner served; international cuisine
COMO Castello Del Nero

COMO Castello Del Nero

COMO Castello Del Nero
5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (133)
Surrounded by rolling hills, this elegant hotel offers two restaurants serving international cuisine. Enjoy complimentary breakfast before exploring nearby Castello di Barberino Val d'Elsa or unwinding with hot stone massages and Ayurvedic treatments at the spa.
"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "
United States
Matthew
The price is Rp12.613.254
Rp14.032.480 total
includes taxes & fees
5 Jan - 6 Jan 2026
COMO Castello Del Nero
2 indoor pools, seasonal outdoor pool
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 Rp11.394.723
Rp12.731.571 total
includes taxes & fees
1 Jan - 2 Jan 2026
Castel Monastero - The Leading Hotels of the World
Terrace/patio
Residenza d'Epoca Relais Campo Regio

Residenza d'Epoca Relais Campo Regio

Residenza d'Epoca Relais Campo Regio
Siena City Centre
9.8 out of 10, Exceptional, (90)
This historic B&B in Siena offers free breakfast, room service, and massage treatments. The cosy bar creates a perfect spot to unwind after exploring nearby Casa di Santa Caterina and Fontebranda attractions.
"It was the best cleanliness and quality of service, warmth and so beautiful pleasant stay!!! )))"
United States
elina
The price is Rp3.677.124
Rp4.123.787 total
includes taxes & fees
1 Jan - 2 Jan 2026
Residenza d'Epoca Relais Campo Regio
Room amenity
Siena Vip

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 accommodation.
"A great location!"
Canada
Cheryl
The price is Rp2.354.521
Rp2.668.924 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip
Porch
Relais degli Angeli

Relais degli Angeli

Relais degli Angeli
Siena City Centre
9.8 out of 10, Exceptional, (281)
Set in the heart of Siena, this charming inn offers a rooftop terrace with city views. Hiking trails nearby provide outdoor adventure, while Palazzo Salimbeni and Piazza Salimbeni are just around the corner. Siena Station is an 18-minute walk away.
"Very central and walkable. Wonderful staff and room was clean and comfortable. "
United States
Kristin
The price is Rp2.797.984
Rp3.156.995 total
includes taxes & fees
30 Dec - 31 Dec
Relais degli Angeli
Seasonal outdoor pool
La Rocca della Magione

La Rocca della Magione

La Rocca della Magione
Monteriggioni
9.4 out of 10, Exceptional, (6)
"Lovely property in a 13th century convent. Situated on a hill overlooking a valley. Family owned, very sweet staff. Visitors (esp Americans) should know the owners speak little to no English, so come with your google translate or try and learn a little Italian prior. One major thing I learned in Italy is the importance of communicating your arrival plan with your host prior to arrival as many establishments are family owned and operated. Owner was very accommodating even though we were...
United States
Jennifer
La Rocca della Magione
Terrace/patio
Villa del Sole Siena

Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (627)
This business-friendly hotel offers free breakfast and WiFi near All'Orto de' Pecci and Piazza del Mercato. Enjoy drinks at the bar or snacks from the deli before relaxing in the garden. Guests consistently praise the exceptionally helpful staff.
"Beautiful small hotel with an exceptional staff. "
United States
Raymond
The price is Rp2.549.546
Rp2.863.910 total
includes taxes & fees
11 Jan - 12 Jan 2026
Villa del Sole Siena
Free daily buffet breakfast
Terre di Baccio

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (71)
Surrounded by Chianti countryside near Piazza Matteotti, this charming affittacamere offers wine lovers a perfect retreat with an on-site winery, poolside bar, and hot tub. Indulge in free breakfast before exploring museum-rich Florence.
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
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 Rp6.708.535
Rp7.438.798 total
includes taxes & fees
26 Dec - 27 Dec
Hotel Certosa Di Maggiano
Down duvets, minibar, in-room safe, individually decorated
Quattro Cantoni

Quattro Cantoni

Quattro Cantoni
Siena City Centre
9.0 out of 10, Wonderful, (81)
Charming B&B in the heart of Siena offers free WiFi and convenient airport shuttle service. Just moments from Pinacoteca Nazionale and the Natural History Museum, this cosy retreat puts Italian cultural gems at your doorstep.
"It was nice, clean. Easy keyless access"
United States
Tabatha
The price is Rp1.240.262
Rp1.443.440 total
includes taxes & fees
7 Jan - 8 Jan 2026
Quattro Cantoni
Exterior
Relais Poggio Borgoni

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 Rp1.884.792
Rp2.152.222 total
includes taxes & fees
25 Dec - 26 Dec
Relais Poggio Borgoni
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)
Wake up to vineyard views at this charming B&B featuring a seasonal outdoor pool and complimentary breakfast. Just a 3-minute drive from Ponticino Station, this tranquil retreat offers easy access to the Buriano Bridge and Penna Natural Reserve.
"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
Free WiFi
Albergo Centrale

Albergo Centrale

Albergo Centrale
2.0 star property
Siena City Centre
8.8 out of 10, Excellent, (90)
Discover Siena's charm from this ideal spot near Piazza del Campo. With free WiFi and daily housekeeping, explore nearby attractions like Siena State Archives and Palazzo Piccolomini. Train station just 9 minutes by car.
"Loved our stay. Vicky was marvellous and helped us with everything. It was a wonderful stay, we will be back!"
Canada
Robert
The price is Rp1.458.220
Rp1.663.451 total
includes taxes & fees
25 Dec - 26 Dec
Albergo Centrale
Property entrance
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 Rp2.462.720
Rp2.787.943 total
includes taxes & fees
8 Jan - 9 Jan 2026
Villa il Fedino
Indoor pool, seasonal outdoor pool, pool loungers
Hotel Palazzo San niccolò & Spa

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 Rp1.566.767
Rp1.841.869 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Palazzo San niccolò & Spa
Exterior
Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (201)
Experience Tuscan charm at this wine resort with an attached winery and Osteria di Fonterutoli restaurant serving Italian cuisine. Located in Castellina in Chianti near Mazzei Winery and Walls of Monteriggioni, guests love the helpful staff.
"Amazing experience all around! Stayed for 2 nights!"
Canada
Matthew
The price is Rp3.052.158
Rp3.436.324 total
includes taxes & fees
25 Dec - 26 Dec
Castello di Fonterutoli Wine Resort
Rooftop terrace
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
Desk, laptop workspace, cots/infant beds, free WiFi
Hotel Il Giardino

Hotel Il Giardino

Hotel Il Giardino
Siena Historical Center
8.6 out of 10, Excellent, (207)
Escape to this tranquil haven featuring a seasonal outdoor pool with poolside bar. Located near San Spirito and Basilica di Santa Maria dei Servi, guests enjoy fitness facilities, a health club, and a café. Free WiFi and parking complete your Italian retreat.
"Simply wonderful place to stay if you’re gonna go and enjoy the city of Sienna. You can walk to everything we would’ve loved to use the pool but it was a bit cold and the views from the breakfast bar were breathtaking."
Australia
Matthew
The price is Rp1.483.015
Rp1.690.529 total
includes taxes & fees
21 Jan - 22 Jan 2026
Hotel Il Giardino
View from property
Hotel Alma Domus

Hotel Alma Domus

Hotel Alma Domus
1.0 star property
Siena City Centre
8.8 out of 10, Excellent, (774)
Enjoy panoramic views of Siena from this central hotel where a complimentary buffet breakfast starts each morning. The 24-hour front desk staff receives high marks from guests, and the location near Fontebranda and Casa di Santa Caterina can't be beat.
"Great breakfast, clean rooms and wonderful area"
Canada
Treena
Hotel Alma Domus
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
"Great location, very friendly staff"
Bennie 2-night trip
Posted 11 days ago
Hotel Athena

More cheap stays in Montegrossi

Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
The price is Rp1.399.579 per night from 25 Dec to 26 Dec
Rp1.399.579
Rp1.598.749 total
25 Dec - 26 Dec
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.