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

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Gaiole in Chianti holiday rentals

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 £112
includes taxes & fees
12 Nov - 13 Nov
L' Eroico
A dining area with a table and chairs, a sofa, and large windows with curtains.

2. 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is £707
includes taxes & fees
10 Nov - 11 Nov
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

3. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is £1,297
additional charges may apply
15 Nov - 16 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A swimming pool with a colorful inflatable ring and a water fountain.

4. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."
Germany
Johanna K.
The price is £396
includes taxes & fees
11 Nov - 12 Nov
Farmhouse in Chianti
A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

5. Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
The price is £244
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

6. Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Gaiole in chianti
The price is £260
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

7. Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
The price is £345
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

8. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is £108
includes taxes & fees
10 Nov - 11 Nov
Agriturismo La Ferrozzola
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

9. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is £99
includes taxes & fees
11 Nov - 12 Nov
Casa Vacanze Squarcialupi
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...
United States
Michael F.
The price is £129
includes taxes & fees
10 Nov - 11 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
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.

11. 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 £216
includes taxes & fees
10 Nov - 11 Nov
Terre di Baccio
A stone building with a patio area featuring a table and chairs under a large umbrella.

12. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (276 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is £76
includes taxes & fees
26 Nov - 27 Nov
Relais Villa Olmo - Place of Charme
A table with breakfast items and a view of rolling hills.

13. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is £57
includes taxes & fees
10 Nov - 11 Nov
Chianti Village Morrocco
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

14. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (34 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is £62
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel
A cozy living room with a stone wall, a wine rack, and two sofas.

15. 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 £78
includes taxes & fees
10 Nov - 11 Nov
Villa Cassia di Baccano
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

16. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is £131
includes taxes & fees
12 Nov - 13 Nov
Relais Villa Belpoggio - Residenza d'Epoca
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

17. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (61 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is £83
includes taxes & fees
12 Nov - 13 Nov
Guild Living Siena Senior Resort & Residence
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

18. 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 £91
includes taxes & fees
1 Dec - 2 Dec
Antica Pieve B&B
An arched entrance with a lantern above, flanked by two potted plants.

19. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is £134
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino
A pool area with lounge chairs and umbrellas, surrounded by trees and buildings.

20. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,805 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is £48
includes taxes & fees
9 Dec - 10 Dec
Hu Firenze Camping In Town
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

8/10 Good
"As a family friendly place we would appreciate having a bigger playground for kids, what you currently offer is nice but very basic and small compared to your other locations in Rome."
Katherine 1-night trip
Posted 1 day ago
Hu Firenze Camping In Town

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 £36 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 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 kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 18 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 Terme Antica Querciolaia. 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.