Holiday Rentals in Chianti Region

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Holiday Rentals in Chianti Region

Our top choices for Chianti Region holiday rentals

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (304)
"Great friendly fun camp site"
Hu Norcenni Girasole Village

Relais Villa Olmo

9.4 out of 10, Exceptional, (223)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
The price is €368
includes taxes & fees
1 Oct - 2 Oct
Relais Villa Olmo

Camping Village Il Poggetto

3.0 star property
8.0 out of 10, Very good, (60)
"Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant "
The price is €65
includes taxes & fees
19 Sept - 20 Sept
Camping Village Il Poggetto

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (63)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Rocca Palazzaccio

3.0 star property
9.0 out of 10, Wonderful, (13)
"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...
Rocca Palazzaccio

Palazzo Pacini

9.8 out of 10, Exceptional, (94)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
The price is €143
includes taxes & fees
5 Oct - 6 Oct
Palazzo Pacini

Relais Villa Belvedere

9.2 out of 10, Wonderful, (67)
"Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer."
The price is €97
includes taxes & fees
19 Oct - 20 Oct
Relais Villa Belvedere

Castello Del Nero - Podere San Filippo

10.0 out of 10, Exceptional, (37)
"Much nicer stay then the rooms at the Como"
Castello Del Nero - Podere San Filippo

Riserva di Fizzano Residence

3.0 star property
9.8 out of 10, Exceptional, (22)
"We had 2 beautiful days here in Chianti. Lovely property with a very good restaurant. Stunning views over the vineyards and Tuscany hills. Close drive to interesting cites. And the wine.... love to come back, and can absolutely recomend a stay here."
The price is €195
includes taxes & fees
12 Oct - 13 Oct
Riserva di Fizzano Residence

Villa with large garden in the Chianti hills

9.6 out of 10, Exceptional, (72)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills

Chianti Village Morrocco

3.0 star property
8.6 out of 10, Excellent, (102)
"Front desk was very helpful and very comfortable room. "
Chianti Village Morrocco

Villa San Filippo

4.0 star property
8.4 out of 10, Very good, (40)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
Villa San Filippo

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (40)
"Very spacious and clean villa in between Florence and Siena in the heart of Chianti. Tremendous hosts that communicated often and met a couple special requests. Have already referred this listing and will definitely come back!"
Your panoramic house in Tuscany between vineyards and olive groves.

Borgo Argenina

9.8 out of 10, Exceptional, (22)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
Borgo Argenina

Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

10.0 out of 10, Exceptional, (80)
"Our family of eight spent twelve days at Villa Le Colline. The Villa was the perfect location from which to tour various areas of Italy. We could not have been more pleased. The home, grounds and views are much more beautiful than the pictures showed! It was a wonderful stay, and we would highly recommend this Villa for large families spending several days in the area. "
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

10.0 out of 10, Exceptional, (41)
"We celebrated our 25th wedding anniversary with friends. It was a beautiful property with the most amazing views. This family owned and operated property was well taken care of. The service was exceptional."
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (3)
"Beautiful villa and stunning location. The host was very responsive and helpful. I would love to return someday. "
Private villa in the heart of chianti with view of siena

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

9.8 out of 10, Exceptional, (51)
"Great location in the heart Chianti. The host was very welcoming and the apartment was perfect. very comfortable bed and very quiet location. Nice terrace and pool but unfortunately the weather wasnt warm enough for us to enjoy the pool. There is a dirt road to get to the apartment but very easy to navigate so dont be worried about it. Thank you Babette, we hope to have the pleasure of going back sometime."
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

detached villa with private pool and garden

8.8 out of 10, Excellent, (25)
"We had a lovely stay. The house is quit near the village but no to near. It is quiet at night. Any problems were fixed very fast. The house offers wonderful views along with a small but very clean pool. It is very near Siena and Florence which makes it an ideal base for trips"
detached villa with private pool and garden
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 Chianti Region Hotel Reviews

Find out more about Chianti Region

Find out more about Chianti Region

Everything you need to know about Chianti Region 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 Chianti Region 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 Chianti Region holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chianti Region holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. 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 Chianti Region 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 Chianti Region holiday rentals we have selected for you start as low as €65 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chianti Region rentals

At Expedia, we put the best Chianti Region 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 Chianti Region 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 Chianti Region 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 Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.