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
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 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 SAR 498
SAR 581 total
includes taxes & fees
13 Nov - 14 Nov
L' Eroico
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is SAR 629
SAR 692 total
includes taxes & fees
21 Oct - 22 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, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is SAR 405
SAR 462 total
includes taxes & fees
18 Oct - 19 Oct
Villa Curina Resort
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

4. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (57 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
Villa Rosa Panzano
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

5. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is SAR 497
SAR 564 total
includes taxes & fees
14 Oct - 15 Oct
Residenzia del Sogno
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

6. 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 SAR 324
SAR 373 total
includes taxes & fees
16 Oct - 17 Oct
Mariani Bed & Breakfast
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

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 SAR 1,064
SAR 1,187 total
includes taxes & fees
19 Oct - 20 Oct
Terre di Baccio
A bakery display with pastries and a coffee station.

8. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is SAR 275
SAR 320 total
includes taxes & fees
13 Nov - 14 Nov
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

9. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (489 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is SAR 417
SAR 475 total
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

10. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
Ca' Bianca Tuscany Relais
A dining area with a table set for two, featuring a view of greenery through a window.

11. 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 SAR 499
SAR 566 total
includes taxes & fees
8 Nov - 9 Nov
La Locanda di Pietracupa
An arched entrance with a lantern above, flanked by two potted plants.

12. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is SAR 777
SAR 872 total
includes taxes & fees
21 Oct - 22 Oct
Villa il Fedino
A cozy living room with a stone wall, a wine rack, and two sofas.

13. 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 SAR 465
SAR 511 total
includes taxes & fees
21 Oct - 22 Oct
Villa Cassia di Baccano
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

14. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 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 SAR 628
SAR 708 total
includes taxes & fees
10 Nov - 11 Nov
PALAZZO DEL PAPA
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

15. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is SAR 434
SAR 495 total
includes taxes & fees
15 Oct - 16 Oct
B&B La Fonte del Machiavelli
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

16. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (75 reviews)
"Wonderful place, great location."
United States
Khaled
The price is SAR 359
SAR 412 total
includes taxes & fees
13 Nov - 14 Nov
B&B Palazzo del Magnifico
A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (99 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 SAR 249
SAR 290 total
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
A view of a traditional European town with stone buildings, a church with a bell tower, and a tiled roof.

18. Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.2 out of 10, Very good, (18 reviews)
"Beautiful view from our room at the top"
United States
ralph
The price is SAR 317
SAR 365 total
includes taxes & fees
10 Nov - 11 Nov
Birbo Bike Hospitality
A building with a sign reading 'Villa Le Camelie' and multiple flags.

19. Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is SAR 306
SAR 353 total
includes taxes & fees
29 Oct - 30 Oct
Villa le Camelie Siena
A stone courtyard with a bench, potted plants, and a building in the background.

20. 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 SAR 379
SAR 429 total
includes taxes & fees
9 Nov - 10 Nov
Casa di Campagna in Toscana
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"The place was very clean, customer service was excellent, especially Caro who checked us in. We felt very safe and site is accessible to city centre. However, there are quite a number of areas to improve on: no chairs, or at minimum, stools in rooms/ glamptents, no tables, more hangers, basic toiletries like hand towels or hand soap. No space in washroom to put your toiletries. Laundry area is clean but very few dryers for the number of people who are in the site. There were I think only 5, the 6th one was out of service. Only a small table ti fold laundry, seemed like an afterthought to put in a small table. When we did our laundry, 2 people had left their dried laundry in 4 machines, 1 was being used. We were left with no machines and were told at reception that machines automatically shut off at 11. It was 1030 and wondering if we’d be able to make it in time."
Clarence 2-night trip
Posted 1 hour ago
Hu Firenze Camping In Town