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Aug 15 - Aug 16
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Aug 16 - Aug 17
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Aug 21 - Aug 23
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Our top choices for Montegrossi hotels

Hotel
Breakfast included
Gaiole in Chianti Stadium
Reserve now, pay later
Airport shuttle included

1. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
United States
Hannah
$156 nightly
$181 total
Sep 9 - Sep 10
Total with taxes and fees
Ultimo Mulino Wellness Country Hotel

2. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
$369 nightly
$418 total
Sep 6 - Sep 7
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World

3. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
United States
Paula
$140 nightly
$159 total
Aug 30 - Aug 31
Total with taxes and fees
Agriturismo San Sano

4. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Austin
$211 nightly
$242 total
Aug 25 - Aug 26
Total with taxes and fees
Castello di Tornano Wine Resort

5. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Edyta
$67 nightly
$83 total
Sep 8 - Sep 9
Total with taxes and fees
La Certosa di Pontignano

6. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
Canada
tera
$203 nightly
$231 total
Aug 24 - Aug 25
Total with taxes and fees
Relais Vignale & Spa

7. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
Canada
Elizabeth
$123 nightly
$143 total
Aug 23 - Aug 24
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa

8. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
$392 nightly
$438 total
Sep 15 - Sep 16
Total with taxes and fees
Chapter Chianti, a Member of Design Hotels

9. Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
$423 nightly
$470 total
Aug 23 - Aug 24
Total with taxes and fees
Podere L'Aquila

10. Hotel Il Viandante

Hotel Il Viandante
Terranuova Bracciolini
United States
Michelle
$113 nightly
$130 total
Aug 18 - Aug 19
Total with taxes and fees
Hotel Il Viandante

11. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
United States
gary
$127 nightly
$147 total
Aug 23 - Aug 24
Total with taxes and fees
Hotel Palazzo San niccolò & Spa

12. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
United States
Rory
$327 nightly
$369 total
Aug 25 - Aug 26
Total with taxes and fees
Dievole Wine Resort

13. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
United States
Giancarlo
$174 nightly
$196 total
Aug 18 - Aug 19
Total with taxes and fees
Castello di Fonterutoli Wine Resort

14. Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
United States
Peter
$59 nightly
$67 total
Aug 23 - Aug 24
Total with taxes and fees
Palagina la cascina

15. Hotel Valdarno

Hotel Valdarno
Montevarchi
United States
Emmanuel
$104 nightly
$115 total
Aug 16 - Aug 17
Total with taxes and fees
Hotel Valdarno

16. Palagina la Dimora

Palagina la Dimora
Figline e Incisa Valdarno
Canada
Tarek
$60 nightly
$68 total
Sep 1 - Sep 2
Total with taxes and fees
Palagina la Dimora

17. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
United States
Scott
$109 nightly
$123 total
Aug 21 - Aug 22
Total with taxes and fees
Hotel Colle Etrusco Salivolpi

18. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
United States
Shane
$158 nightly
$173 total
Sep 1 - Sep 2
Total with taxes and fees
Castello Vicchiomaggio

19. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
United Kingdom
Jess
$137 nightly
$157 total
Aug 26 - Aug 27
Total with taxes and fees
Belvedere di San Leonino

20. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Jason
$154 nightly
$174 total
Aug 23 - Aug 24
Total with taxes and fees
Villa Casagrande Resort & SPA
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Top Montegrossi Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"
C 3-night trip
Posted 23 hours ago
Villa Casagrande Resort & SPA
Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It’s a nice enough property, but certainly not four or five star. I did enjoy my stay. The staff were phenomenal. The room was fine. I only was there for one night. The breakfast was so no food at all."
Joseph 1-night trip
Posted 1 day ago
Hotel Chiusarelli
Hotel Athena

Hotel Athena

10/10 Excellent
"Wonderful hotel in great location just a short walk from the centre but quiet and peaceful in the evening. Fabulous helpful staff. Breakfast always fresh and lots of choice. We used the terrace restaurant once and it was fabulous - what amazing views! Highly recommended for a short or longer stay"
Richard 7-night trip
Posted 9 days ago
Hotel Athena
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."
Nicholas 7-night trip
Posted 10 days ago
Borgo Scopeto Wine & Country Relais
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 11 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."
Frederic 4-night trip
Posted 11 days ago
La Certosa di Pontignano
Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Beautiful hotel and helpful staff Excellent food and amenities"
Onix 2-night trip
Posted 11 days ago
Hotel Borgo San Luigi
Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"Very enjoyable stay"
Nigel 3-night trip
Posted 13 days ago
Villa Scacciapensieri Boutique Hotel
Castello di Leonina Relais

Castello di Leonina Relais

8/10 Good
"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."
Anthony 2-night trip
Posted 1 month ago
Castello di Leonina Relais

More cheap stays in Montegrossi

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
$87 nightly
$101 total
Aug 22 - Aug 23
Total with taxes and fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
$97 nightly
$112 total
Aug 20 - Aug 21
Total with taxes and fees
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
$98 nightly
$114 total
Aug 18 - Aug 19
Total with taxes and fees
8.8/10 Excellent! (104 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
$100 nightly
$116 total
Aug 18 - Aug 19
Total with taxes and fees
10/10 Exceptional! (48 reviews)
Torre del Fuggisole
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
$217 nightly
$244 total
Aug 29 - Aug 30
Total with taxes and fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get rates
9.4/10 Exceptional! (23 reviews)
Porta Pispini Residence

Hotels in Montegrossi with star-rating

Frequently asked questions

Where is the best place for a stay in Montegrossi?
Located 12.7 mi (20.5 km) from the heart of Montegrossi, Grand Hotel Continental Siena – Starhotels Collezione is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Hotel Athena and Borgo Scopeto Wine & Country Relais. 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 espresso maker. 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, Meleto Castle, and Cantalici Winery. You'll also find Castello di Albola and Castello di Radda Winery 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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