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
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 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 3.320.613 ₫
3.883.288 ₫ total
includes taxes & fees
9 Nov - 10 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 4.818.138 ₫
5.299.952 ₫ total
includes taxes & fees
31 Oct - 1 Nov
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, (83 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is 3.396.518 ₫
3.851.765 ₫ total
includes taxes & fees
31 Oct - 1 Nov
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 3.406.805 ₫
3.862.792 ₫ total
includes taxes & fees
31 Oct - 1 Nov
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
Mariani Bed & Breakfast
An arched entrance with a lantern above, flanked by two potted plants.

6. 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 4.123.111 ₫
4.651.017 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino
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, (82 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 6.981.329 ₫
7.794.769 ₫ total
includes taxes & fees
8 Nov - 9 Nov
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, (495 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 2.579.082 ₫
2.952.297 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Siena Vip
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

9. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (218 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is 1.894.551 ₫
2.199.313 ₫ total
includes taxes & fees
8 Nov - 9 Nov
B&B Il Corso
A cozy living room with a stone wall, a wine rack, and two sofas.

10. 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 2.969.999 ₫
3.266.999 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Villa Cassia di Baccano
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

11. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (93 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is 2.987.506 ₫
3.401.564 ₫ total
includes taxes & fees
2 Nov - 3 Nov
B&B La Fonte del Machiavelli
A table with two wine glasses, a bottle, and a book.

12. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (102 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is 1.682.857 ₫
1.966.737 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
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
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is 3.734.225 ₫
4.222.839 ₫ total
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa
A historic building with a clock tower, arched windows, and a shop selling souvenirs.

14. 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 4.652.451 ₫
5.233.003 ₫ total
includes taxes & fees
7 Nov - 8 Nov
PALAZZO DEL PAPA
A stone-paved courtyard with a wrought iron gate, a brick building, and a tree.

15. B&B Le Logge Di Sopra

B&B Le Logge Di Sopra
Asciano
The price is 2.688.756 ₫
3.072.938 ₫ total
includes taxes & fees
24 Nov - 25 Nov
B&B Le Logge Di Sopra
A stone courtyard with a bench, potted plants, and a building in the background.

16. 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 2.153.532 ₫
2.455.581 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
A building with a sign reading 'Villa Le Camelie' and multiple flags.

17. 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 2.096.574 ₫
2.421.452 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Villa le Camelie Siena
An arched stone bridge with a white building on the right, featuring a balcony with plants.

18. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (21 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is 3.013.712 ₫
3.315.083 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Locanda Antico Borgo
A traditional stone building with a courtyard, a staircase, and potted plants.

19. 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
Il Pozzo di Sant'Andrea
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

20. 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 2.505.023 ₫
2.870.832 ₫ total
includes taxes & fees
8 Nov - 9 Nov
B&B Palazzo del Magnifico
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

Hotel Athena

Hotel Athena

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 20 hours ago
Hotel Athena

Find out more about Gaiole in Chianti

Gaiole in Chianti Town Houses information

Number of reviews
534
Accommodation
114 Town Houses
Lowest Price
1.966.737 ₫
Highest Price
7.794.769 ₫