Chianti Region Cheap Holidays
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Top flight + Cheap hotel deals in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Save 100% on your flight
Price was £550, price is now £408 per person
£408
per person
5 Jul - 10 Jul
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (431 reviews)
We loved staying here and the staff was amazing. Unfortunately the weather didn't allow us to enjoy being outside in their gorgeous gardens much but we did have some spectacular views of Siena when we did.
We didn't realize when we booked how far from city centre we would be, but the good thing was that the bus picked us up at the bottom of the driveway and for 1.70 each took us to the city centre .
Also, even though the loft in our unit was beautiful, i didn't expect that the washroom would be downstairs which wasn't so convenient in the middle of the night.
Breakfast buffet was great and cappuccino and café latte made for us upon request, was very delicious
Reviewed on 12 May 2026
Relais Castel Bigozzi
Save 100% on your flight
Price was £753, price is now £573 per person
£573
per person
17 Jul - 24 Jul
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
8.8/10 Excellent! (243 reviews)
Place is gorgeous and the grounds are stunning.
Wifi is not the best and could use improvement
Reviewed on 18 Mar 2026
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Hotel Chiusarelli
Siena City Centre
Price was £333, price is now £292 per person
£292
per person
31 Jul - 4 Aug
found 19 hours ago
Return flight included
Manchester (MAN) to Florence (FLR)
8.8/10 Excellent! (1,006 reviews)
This is a great location in Siena, close to all the sights. Just a note that there is no elevator, but the front desk man kindly carried my luggage up to the 2nd floor which was great. My only challenge was that the room was very warm (25.3C), and there was no working fan to move air around. I did ask at the front desk, and apparently the system had not been activated, and the AC was not yet running. Therefore I had to have my windows open all night and there was road noise. My friend had a lovely room on the first floor at the back of the building with a garden patio and we enjoyed that.
They have an excellent breakfast. I would stay here again but would make sure they had fans or AC in the room.
Reviewed on 11 May 2026
Relais Castel Bigozzi
Price was £566, price is now £504 per person
£504
per person
6 Jul - 10 Jul
found 2 hours ago
Return flight included
Bristol (BRS) to Florence (FLR)
8.8/10 Excellent! (243 reviews)
Place is gorgeous and the grounds are stunning.
Wifi is not the best and could use improvement
Reviewed on 18 Mar 2026
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View all tripsTop Cheap Chianti Region Hotels
Sangallo Park Hotel
Strada Di Vico Alto 2 Siena SI
Stay at this business-friendly hotel in Siena. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Palasport Mens Sana and Siena Stadium are ...
9/10 Wonderful! (608 reviews)
Every staff that we spoke to were friendly and very good in helping us with all the questions that we had. Hotel location is good in that it is away from the busy civic center but within just a short driving distance.
Reviewed on 8 May 2026
La Perla
Via Delle Terme 25 Siena SI
Stay at this hotel in Siena. Enjoy free Wi-Fi, daily housekeeping and pillowtop beds. Popular attractions Teatro dei Rozzi and Loggia della Mercanzia are located ...
7.8/10 Good! (301 reviews)
The property was very close to lots of dining options and the town centre. Check in communication was good and the room was compact but perfect for a 2 night stay. would stay there again
Reviewed on 21 Apr 2026
LHP Certaldo Resort
via del Molino, 74 Certaldo FI
Stay at this luxury hotel in Certaldo. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.2/10 Wonderful! (530 reviews)
The staff were excellent, especially Carim.
Reviewed on 10 May 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
