A stone castle with battlements overlooking a lush valley with vineyards.

Search Town Houses in Gaiole in Chianti

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for Gaiole in Chianti town houses

A stone building with a yellow sign reading "b&b erioico".

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is AU$215
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A hot tub with two glasses of a beverage.

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is AU$279
includes taxes & fees
29 Oct - 30 Oct
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

3. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is AU$218
includes taxes & fees
25 Oct - 26 Oct
Villa Curina Resort
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

4. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is AU$214
includes taxes & fees
24 Oct - 25 Oct
Residenzia del Sogno
A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

5. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is AU$151
includes taxes & fees
24 Oct - 25 Oct
Mariani Bed & Breakfast
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

6. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (76 reviews)
"Wonderful place, great location."
United States
Khaled
The price is AU$164
includes taxes & fees
12 Nov - 13 Nov
B&B Palazzo del Magnifico
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

7. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is AU$438
includes taxes & fees
30 Oct - 31 Oct
Terre di Baccio
A bathroom with a window view of a historic building and a tiled roof.

8. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (494 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is AU$181
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
A historic building with a clock tower, arched windows, and a shop selling souvenirs.

9. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is AU$290
includes taxes & fees
7 Nov - 8 Nov
PALAZZO DEL PAPA
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

10. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (91 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is AU$189
includes taxes & fees
25 Oct - 26 Oct
B&B La Fonte del Machiavelli
A table with two wine glasses, a bottle, and a book.

11. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (100 reviews)
"Place was great, beautiful, modern, well maintained and staff was very helpful. I didn’t like that it is far from everything, far from train station, not too many options for food in the vicinity."
United States
Waleska
The price is AU$116
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
A cozy living room with a stone wall, a wine rack, and two sofas.

12. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$170
includes taxes & fees
23 Nov - 24 Nov
Villa Cassia di Baccano
A two-story house with a patio area, potted plants, and outdoor furniture.

13. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is AU$223
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa
Pool

14. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is AU$126
includes taxes & fees
16 Nov - 17 Nov
iConic Wellness Resort
An arched entrance with a lantern above, flanked by two potted plants.

15. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is AU$337
includes taxes & fees
26 Oct - 27 Oct
Villa il Fedino
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

16. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is AU$238
includes taxes & fees
24 Oct - 25 Oct
Antica Pieve B&B
A stone courtyard with a bench, potted plants, and a building in the background.

17. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is AU$148
includes taxes & fees
23 Nov - 24 Nov
Casa di Campagna in Toscana
A traditional stone building with a courtyard, a staircase, and potted plants.

18. Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is AU$171
includes taxes & fees
26 Oct - 27 Oct
Il Pozzo di Sant'Andrea
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

19. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (216 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is AU$122
includes taxes & fees
3 Nov - 4 Nov
B&B Il Corso
An open wooden door leading to an outdoor patio with a table and chairs.

20. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is AU$191
includes taxes & fees
7 Nov - 8 Nov
Palazzo al Torrione 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good
"Excellent location. Very nice service."
mauricio 1-night trip
Posted 3 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Gaiole in Chianti

Gaiole in Chianti Town Houses information

Number of reviews
1,419
Accommodation
114 Town Houses
Lowest Price
AU$116
Highest Price
AU$438

Explore a world of travel with Expedia