Holiday Rentals in Gaiole in Chianti

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Our top choices for Gaiole in Chianti holiday rentals

Townhouse in Gaiole in Chianti

L' Eroico
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

Townhouse in Gaiole in Chianti

Rocca di Castagnoli
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 €168
includes taxes & fees
4 Jan - 5 Jan 2026
Rocca di Castagnoli

Townhouse in Barberino Tavarnelle

La Locanda di Pietracupa
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is €135
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio

Apartment in Siena City Centre

Palazzo Lenzi
9.0 out of 10, Wonderful, (2)
"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "
United States
Daniel
The price is €439
includes taxes & fees
11 Jan - 12 Jan 2026
Palazzo Lenzi

Residence in Impruneta

Rocca Palazzaccio
3.0 star property
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

Aparthotel in Siena City Centre

The Balcony Suite -Piazza del Campo View
9.2 out of 10, Wonderful, (16)
"Perfect location to explore Siena, right on the Campo. The apartment was warm and comfortable. As to be expected in such a central location, the noise & music from then restaurants on the piazza was loud till the early hours on Saturday night (so bring earplugs) but the other night was fine. "
Australia
Nicola
The price is €187
includes taxes & fees
5 Jan - 6 Jan 2026
The Balcony Suite -Piazza del Campo View

Aparthotel in Siena

La Coroncina Lodging
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is €119
includes taxes & fees
14 Jan - 15 Jan 2026
La Coroncina Lodging

Residence in Siena City Centre

Residenza d'Epoca Palazzo Borghesi
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is €178
includes taxes & fees
23 Jan - 24 Jan 2026
Residenza d'Epoca Palazzo Borghesi

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is €85
includes taxes & fees
5 Jan - 6 Jan 2026
Tuscasì Aparthotel

Apartment in Siena City Centre

Astonish Cathedral View
10.0 out of 10, Exceptional, (1)
Astonish Cathedral View

Aparthotel in Asciano

Albergo Diffuso Borgo Santo
The price is €247
includes taxes & fees
1 Jan - 2 Jan 2026
Albergo Diffuso Borgo Santo

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is €141
includes taxes & fees
7 Jan - 8 Jan 2026
Villa il Fedino

Townhouse in Castellina in Chianti

Residenzia del Sogno
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is €134
includes taxes & fees
2 Jan - 3 Jan 2026
Residenzia del Sogno

Apartment in Siena City Centre

Casa Ciseri
9.8 out of 10, Exceptional, (9)
"Very nice stay!"
United States
Danielle
The price is €251
includes taxes & fees
24 Dec - 25 Dec
Casa Ciseri

Townhouse in Siena City Centre

B&B Palazzo del Magnifico
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

Townhouse in Siena City Centre

PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is €184
includes taxes & fees
27 Dec - 28 Dec
PALAZZO DEL PAPA

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is €119
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2

Aparthotel in Siena Historical Center

Villa Liberty TownHouse
10.0 out of 10, Exceptional, (4)
"Amazing place in a perfect location. "
Canada
Ben
The price is €387
includes taxes & fees
28 Dec - 29 Dec
Villa Liberty TownHouse
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

Everything you need to know about Gaiole in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaiole in Chianti holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gaiole in Chianti holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gaiole in Chianti. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gaiole in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gaiole in Chianti holiday rentals we have selected for you start as low as €62 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gaiole in Chianti rentals

At Expedia, we put the best Gaiole in Chianti holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gaiole in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaiole in Chianti holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaiole in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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 an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 30 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.