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Our top choices for Gaiole in Chianti bed & breakfast

Brolio Agriroom

Brolio Agriroom
Gaiole in Chianti
8.8 out of 10, Excellent, (10)
"Ricasoli is stunning, and nice place to stay nearby"
United States
Arturo
$114 nightly
The price is $135
Dec 20 - Dec 21
Total with taxes and fees
Brolio Agriroom

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
"Excellent place to stay even for the next time. "
Canada
Xuejie
$68 nightly
The price is $80
Dec 24 - Dec 25
Total with taxes and fees
La Certosa di Pontignano

Il Sorriso

Il Sorriso
Oltrarno
9.2 out of 10, Wonderful, (129)
"Easy to check in remotely. It was located next to a lot of restaurants and a nice park that we were able to walk to. Angelica, the property manager was so helpful! She provided me with great information on how to check in and use keys to get into the building. "
United States
Natashka
$82 nightly
The price is $104
Dec 20 - Dec 21
Total with taxes and fees
Il Sorriso

Antico Granaione

Antico Granaione
Rapolano Terme
9.8 out of 10, Exceptional, (59)
"old fashion building, clean and affordable"
United States
Irene
$84 nightly
The price is $97
Jan 6 - Jan 7, 2026
Total with taxes and fees
Antico Granaione

Il Chiostro del Carmine

Il Chiostro del Carmine
Siena Historical Center
8.6 out of 10, Excellent, (870)
"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
$72 nightly
The price is $84
Jan 7 - Jan 8, 2026
Total with taxes and fees
Il Chiostro del Carmine

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)
"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
$108 nightly
The price is $118
Dec 23 - Dec 24
Total with taxes and fees
B&B Country House Poggio del Drago

Antiche Mura

Antiche Mura
Arezzo Centro Storico
9.4 out of 10, Exceptional, (86)
"It was my second stay at the Antiche Mura, and I was pleased to find that it remains a very comfortable place right in the middle of the city, near the main cathedral. "
United States
Dennis
$76 nightly
The price is $90
Jan 11 - Jan 12, 2026
Total with taxes and fees
Antiche Mura

Chiantirooms Guesthouse

Chiantirooms Guesthouse
Greve in Chianti
9.8 out of 10, Exceptional, (34)
"Friendly host and great place to stay. "
Canada
Pasquale
$109 nightly
The price is $125
Jan 7 - Jan 8, 2026
Total with taxes and fees
Chiantirooms Guesthouse

Quattro Cantoni

Quattro Cantoni
Siena City Centre
9.0 out of 10, Wonderful, (81)
"Absolutely loved this stay. The staff were incredibly helpful and got me taxis etc when I needed them. The room was so comfortable with high tech support for working and relaxing. The meals were absolutely delicious and served with great customer service. This was a gem of a place to stay. The area is also beautiful and has much to offer in terms of a relaxing stay. I would happily go again! "
United Kingdom
Yvonne
$71 nightly
The price is $83
Jan 12 - Jan 13, 2026
Total with taxes and fees
Quattro Cantoni

San Sebastiano Suite & Luxury

San Sebastiano Suite & Luxury
Colle di Val d'Elsa
8.6 out of 10, Excellent, (7)
"Great location and beautiful place to stay. Loved the interior decorating and host was good too. Would stay again. "
Canada
Nadia
$77 nightly
The price is $87
Dec 23 - Dec 24
Total with taxes and fees
San Sebastiano Suite & Luxury

Torrebianca Tuscany

Torrebianca Tuscany
Rignano sull'Arno
9.6 out of 10, Exceptional, (40)
"Lovely pool Breakfast good"
United Kingdom
christine
$103 nightly
The price is $115
Jan 11 - Jan 12, 2026
Total with taxes and fees
Torrebianca Tuscany

Arnolfo B&B

Arnolfo B&B
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (26)
"Stunning property in a cute hilltop town. Garden with tables and lounge chairs to have breakfast or hang out in the evenings. The rooms have nice details and good quality beds. "
France
Elsa
$95 nightly
The price is $107
Dec 30 - Dec 31
Total with taxes and fees
Arnolfo B&B

B&B Le Caselle

B&B Le Caselle
Lucignano
9.2 out of 10, Wonderful, (23)
"Cozy place in nice ambience, close to small historical village. Super friendly team, and also arranged pizza for me even though I had a late 10pm arrival. Great stay!"
Norway
Anonymous traveler
$108 nightly
The price is $119
Dec 22 - Dec 23
Total with taxes and fees
B&B Le Caselle

Poggio Baronti B&B

Poggio Baronti B&B
Bagno a Ripoli
10.0 out of 10, Exceptional, (155)
"The location is excellent for traveling both to Florence and to Toscana. The facility is in a perfect condition, clean and modern even though it is an old building. The owner is welcoming and strive to answer any question. "
United States
shimon
$105 nightly
The price is $115
Jan 6 - Jan 7, 2026
Total with taxes and fees
Poggio Baronti B&B

B&B San Francesco

B&B San Francesco
Siena City Centre
9.4 out of 10, Exceptional, (46)
"Very nice enjoyable stay"
United States
Michael
$64 nightly
The price is $75
Jan 12 - Jan 13, 2026
Total with taxes and fees
B&B San Francesco

B&B Poggiobonizio

B&B Poggiobonizio
Poggibonsi
9.2 out of 10, Wonderful, (62)
"Simone is a really nice person, he help us a lot, very friendly, room was clean, breakfast was good. "
United States
Odalis
$69 nightly
The price is $76
Dec 20 - Dec 21
Total with taxes and fees
B&B Poggiobonizio

B&B Il Poggiolo delle Rose

B&B Il Poggiolo delle Rose
Impruneta
9.4 out of 10, Exceptional, (87)
"Great place to stay. The manager (or owner, I am not sure) was very helpful and accomodating, pointing us to the best places to visit/park in Florence city. There were great breakfast options on site and the rooms are very clean despite not being a 5-star hotel. Thank you for hosting us during our 1-night stay in Florence!"
United States
Suzanna
$109 nightly
The price is $124
Jan 10 - Jan 11, 2026
Total with taxes and fees
B&B Il Poggiolo delle Rose

La Dimora Dei Monaci

La Dimora Dei Monaci
Siena City Centre
10.0 out of 10, Exceptional, (86)
"Fantastic accommodations! Very comfortable bed! Spacious room, and beautiful. We definitely recommend."
United States
Karin
$98 nightly
The price is $113
Dec 20 - Dec 21
Total with taxes and fees
La Dimora Dei Monaci

Lantico Gabbiano: Room Terry

Lantico Gabbiano: Room Terry
Toscana
$124 nightly
The price is $129
Dec 21 - Dec 22
Total with taxes and fees
Lantico Gabbiano: Room Terry

B&B Siena in Centro - Diffuso

B&B Siena in Centro - Diffuso
Siena City Centre
8.6 out of 10, Excellent, (162)
"Great staff, good location and quiet"
United States
Molly
$87 nightly
The price is $101
Jan 10 - Jan 11, 2026
Total with taxes and fees
B&B Siena in Centro - Diffuso
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 Gaiole in Chianti Hotel Reviews

Find out more about Gaiole in Chianti

Gaiole in Chianti B&B information

Number of reviews
2,459
Accommodation
163 B&B
Lowest Price
$75
Highest Price
$135

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Gaiole in Chianti?
Prices for B&Bs in Gaiole in Chianti often vary, but you can find a great deal from $75 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Gaiole in Chianti B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
Are there any family-friendly Bed & Breakfasts in Gaiole in Chianti?
Cavarchino B&B is an excellent choice for families visiting Gaiole In Chianti. This charming property stands out with its inclusive setting and thoughtful amenities designed for families. Kids will enjoy the free services such as cribs and sofa beds, ensuring a comfortable stay for everyone. The daily housekeeping and complimentary buffet breakfast add to the convenience, allowing parents to relax and enjoy their time together. The beautiful garden provides a great space for children to play while adults unwind with a good book or a glass of local wine.

Another family-friendly option is Brolio Agriroom, which features connecting rooms, superb for families needing extra space and privacy. This property also includes fun amenities like games for children, ensuring that younger guests are entertained. With a lovely garden, private picnic areas, and a snack bar, families can enjoy casual outdoor dining and quality time together. Daily housekeeping keeps things tidy, making it easier for parents to focus on creating memorable experiences during their getaway.
Do any Gaiole in Chianti Bed and Breakfasts allow dogs?
Cavarchino B&B is a delightful choice for travelers with dogs, offering a friendly setting and a range of amenities that cater to both pets and their owners. This charming property not only permits pets but also provides thoughtful touches like free accommodations for children, making it a great option for families. Guests can enjoy stunning vineyard views while lounging by the seasonal outdoor pool, complete with sun loungers and umbrellas for relaxation after a day of adventure.

Another wonderful option is B&B Borgolecchi, which also allows dogs and provides a serene setting with picturesque vineyard vistas. This property features a lovely patio and terrace where you can unwind with your furry friend, as well as complimentary buffet breakfasts to start your day on a delicious note. With free self-parking and in-room WiFi, it offers the convenience and comfort that families often seek when traveling.
Are there any romantic B&Bs in Gaiole in Chianti for couples?
For couples seeking a romantic escape, the Brolio Agriroom is a delightful bed and breakfast nestled in the picturesque Gaiole In Chianti. This charming property is celebrated for its intimate atmosphere and impressive amenities, making it an ideal retreat for those looking to connect with their partner amidst stunning vineyard landscapes.
When is the best time to book a Bed and Breakfast in Gaiole in Chianti?
The best time to book a B&B in Gaiole In Chianti is during the spring months, particularly April, when the countryside begins to bloom with vibrant colors and the weather is pleasantly mild. This is the great season for travelers who appreciate leisurely vineyard tours and scenic hikes through the rolling hills of Tuscany.

As the peak tourist season stretches from July to September, visitors flock to Gaiole In Chianti to partake in wine festivals and experience the warm Italian sun. While this time offers lively festivities, it can also mean more crowds, especially during popular events like the Chianti Classico Wine Festival. The summer months are ideal for those looking to immerse themselves in the local culture and enjoy outdoor dining under the Tuscan sky.

For those who prefer to avoid the hustle and bustle, visiting in December can be a strategic choice. While it's considered the low season, this month allows for a great experience, with fewer tourists and a chance to enjoy the festive ambiance of local holiday markets. Plus, you can savor the tranquil beauty of the countryside adorned with winter charm.
What is the difference between a Gaiole in Chianti B&B and a hotel?
Every Gaiole in Chianti B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Gaiole in Chianti B&Bs.

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