Chianti Region Cheap Holidays
Book a Cheap Hotel + Flight or Car together to unlock savings
Better together
Save up to £335 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top flight + Cheap hotel deals in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
per person
3 Aug - 8 Aug
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (399 reviews)
Beautiful grounds; lovely and quiet .
Tranquil setting for walking, swimming, napping , viewing the Tuscan sunsets .
Reviewed on 10 Jun 2025
Hotel Certaldo
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
London (LCY) to Florence (FLR)
9.2/10 Wonderful! (512 reviews)
This was a gem. Great stop spot between Rome and Florence. Staff was awesome. All services and amenities were great and our requests were easily looked after. Lobby and hotel in general beautiful. Dinner and buffet breaky were excellent. Very good quality meals and very good service. This place was a top stay for us and if the location is where you may be - you will not regret staying here. Easy free parking ! If you read many reviews and these are important for your decision making, then you will not regret staying here. One of the best !
Reviewed on 25 Apr 2025
Villa San Lucchese
per person
3 Aug - 8 Aug
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.4/10 Exceptional! (325 reviews)
This is a family owned and run hotel with wonderfully hospitable and friendly staff and owners. The owners are there all the time to greet and serve hotel guests. The room was very clean and comfortable and we had a great view from our window. The San Lucchese restaurant is 5 star ! Very good food, wines and service! We love seated outside on its patio with beautiful views of the vineyards from our high hilltop location. The hotel is very well located and we can get to many different attractions in the region within 15-25 minutes drive. We loved it so much that we extended our stay longer. Definitely highly recommend this hotel to anyone looking for a secluded gem away from crowds and stress.
Reviewed on 11 Jun 2025
Don't see what you're looking for?
See all available trips from London to Chianti Region
View all trips3 Night Cheap holidays in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
per person
11 Aug - 14 Aug
found 18 hours ago
Return flight included
London (STN) to Florence (FLR)
9.2/10 Wonderful! (399 reviews)
Beautiful grounds; lovely and quiet .
Tranquil setting for walking, swimming, napping , viewing the Tuscan sunsets .
Reviewed on 10 Jun 2025
Hotel Certaldo
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
London (LCY) to Florence (FLR)
9.2/10 Wonderful! (512 reviews)
This was a gem. Great stop spot between Rome and Florence. Staff was awesome. All services and amenities were great and our requests were easily looked after. Lobby and hotel in general beautiful. Dinner and buffet breaky were excellent. Very good quality meals and very good service. This place was a top stay for us and if the location is where you may be - you will not regret staying here. Easy free parking ! If you read many reviews and these are important for your decision making, then you will not regret staying here. One of the best !
Reviewed on 25 Apr 2025
Don't see what you're looking for?
See all available trips from London to Chianti Region
View all trips4 Night Cheap holidays in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Hotel Chiusarelli
Siena City Centre
per person
26 Aug - 30 Aug
found 15 hours ago
Return direct flight included
London (LON) to Florence (FLR)
8.8/10 Excellent! (1,004 reviews)
This property is beautiful. I love Trompe-l'œil the that they have on the walls all over the hotel. Breakfast was delicious. They do have some onside parking. The biggest problem that I had with this venue is there is no elevator. We were staying in a triple room which are all on the top floor and I walk with a cane which meant there was many many stairs to go up. Other than that I would highly recommend for your Siena trip
Reviewed on 17 Jun 2025
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
per person
26 Aug - 30 Aug
found 15 hours ago
Return direct flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (399 reviews)
Beautiful grounds; lovely and quiet .
Tranquil setting for walking, swimming, napping , viewing the Tuscan sunsets .
Reviewed on 10 Jun 2025
Don't see what you're looking for?
See all available trips from London to Chianti Region
View all tripsTop Cheap Chianti Region Hotels
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 Piazza del Campo and Siena Cathedral are located ...
7.6/10 Good! (274 reviews)
"Great place on a budget!"
Reviewed on 28 Jun 2025
Sangallo Park Hotel
Strada Di Vico Alto 2, Siena, SI
Stay at this 3-star business-friendly hotel in Siena. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Piazza del Campo and Siena Cathedral ...
9/10 Wonderful! (562 reviews)
"Really lovely staff, good breakfast"
Reviewed on 14 Oct 2024
Hotel Certaldo
via del Molino, 74, Certaldo, FI
Stay at this 4-star business-friendly hotel in Certaldo. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (503 reviews)
"This was a gem. Great stop spot between Rome and Florence. Staff was awesome. All services and amenities were great and our requests were easily looked after. Lobby and hotel in general beautiful. Dinner and buffet breaky were excellent. Very good quality meals and very good service. This place was ..."
Reviewed on 25 Apr 2025
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.
More holidays you might like
* 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.