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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Top Holiday Rentals in Gaiole in Chianti

Front of property
L' Eroico

L' Eroico

Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
Outdoor pool, pool loungers
Rocca di Castagnoli

Rocca di Castagnoli

Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is ₹21,432
₹24,413 total
includes taxes & fees
1 Jan - 2 Jan 2026
Rocca di Castagnoli
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

B&B Il Corso

Siena City Centre
9.8 out of 10, Exceptional, (190)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ₹11,199
₹12,738 total
includes taxes & fees
10 Dec - 11 Dec
PALAZZO DEL PAPA
Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ₹12,775
₹14,053 total
includes taxes & fees
9 Dec - 10 Dec
Villa Cassia di Baccano
Birthday party area
Siena Vip

Siena Vip

Siena City Centre
9.2 out of 10, Wonderful, (421)
"A great location!"
Canada
Cheryl
Siena Vip
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Truly a gem! Our room was beautiful with a lovely view. It is very close to the main road and restaurants. Definitely opt in for the breakfast it was absolutely delicious. "
United States
Leasly
The price is ₹8,429
₹12,416 total
includes taxes & fees
15 Dec - 16 Dec
Palazzo al Torrione 2
Chalet | In-room safe, cots/infant beds, bed sheets
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Florence
8.8 out of 10, Excellent, (1610)
"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Exterior detail
Villa il Fedino

Villa il Fedino

San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ₹12,944
₹14,657 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa il Fedino
Balcony
Cameracaffè Centro

Cameracaffè Centro

Arezzo Centro Storico
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is ₹7,828
₹9,239 total
includes taxes & fees
15 Dec - 16 Dec
Cameracaffè Centro
Quadruple Room, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Al Mercato B&B

Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is ₹5,865
₹7,793 total
includes taxes & fees
14 Dec - 15 Dec
Al Mercato B&B
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | View from room
B&B Palazzo del Magnifico

B&B Palazzo del Magnifico

Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (71)
"Very nice place"
United States
Maria
The price is ₹8,951
₹10,004 total
includes taxes & fees
9 Dec - 10 Dec
Relais Villa Belvedere
Terrace/patio
Casa di Campagna in Toscana

Casa di Campagna in Toscana

Sovicille
9.4 out of 10, Exceptional, (18)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

La Coroncina Lodging

Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ₹7,600
₹8,779 total
includes taxes & fees
10 Dec - 11 Dec
La Coroncina Lodging
Grand Apartment with Garden | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Full-sized fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

Rocca Palazzaccio

3.0 star property
Impruneta
9.0 out of 10, Wonderful, (14)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
Rocca Palazzaccio
Outdoor pool, pool loungers
I Parigi Corbinelli

I Parigi Corbinelli

Florence
9.4 out of 10, Exceptional, (162)
"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."
Australia
Tim
The price is ₹6,716
₹8,644 total
includes taxes & fees
12 Dec - 13 Dec
I Parigi Corbinelli
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

Hotel Athena

Hotel Athena

10/10 Excellent
"The hotel is in an excellent location. The room is extremely comfortable and has a beautiful view. All the staff are super friendly, helpful, and always smiling. The breakfast is varied, delicious, and amazing. I would definitely stay here again."
Natalia 1-night trip
Posted 4 days ago
Hotel Athena

Find out more about Gaiole in Chianti

Holiday Rentals in Gaiole in Chianti

Search for holiday rentals in Gaiole in Chianti on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Gaiole in Chianti using one of the methods below:

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Look no further and take a look at our great range of rental properties in Gaiole in Chianti!

Frequently asked questions

Can I find holiday rentals in Gaiole in Chianti?

Yes, there are holiday rentals close to the most popular sights in Gaiole in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. The spas and wineries are several reasons why visitors like Gaiole in Chianti. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Gaiole in Chianti has to offer?

Borgo Argiano: This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 29 Expedia holiday rentals, you're guaranteed to find just the right place for your Gaiole in Chianti stay.

What’s there to see and do in Gaiole in Chianti?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

What’s a holiday rental in Gaiole in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gaiole in Chianti. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.