
Chianti Region Vacation Packages
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4.0-star property
Hotel Palazzo San niccolò & Spa
9.2/10 Wonderful! (187 reviews)
Sep 21 - Sep 26
5 night stay
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
Icelandair • Non-stop • Coach
Florence (FLR) to Newark Liberty Intl. Airport (EWR)
TAP Portugal • Non-stop • Coach
Price was $1,497, price is now $1,064 per person
$1,064
per person
found 1 day ago
This was a little slice of heaven and such a hidden gem. This place is by far my favorite that I have been to in Europe
Reviewed on Jun 16, 2026

4.0-star property
Villa Sabolini
9.2/10 Wonderful! (214 reviews)
Aug 24 - Aug 30
6 night stay
New York (NYC) to Florence (FLR)
ITA Airways • Non-stop roundtrip • Coach
Price was $2,276, price is now $1,700 per person
$1,700
per person
found 1 day ago
We came to this hotel unexpectedly and were so happy we found it.
The staff are truly exceptional, friendly, attentive, accommodating, effective, welcoming. We arrived due to my wife having emergency surgery in Siena, we were supposed to be in Venice, and this hotel staff went to work making sure we were taken care of. The grounds are stunning as well, an amazing place to recover after surgery. The pool is beautiful and the restaurant is fantastic. I truly have enjoyed each meal I have had. The lunch I ordered of sliced beef with rocket, pecorino and tomato was perfectly cooked and so tasty.
The bartender Bruno makes a fantastic Negroni and I have had the chance to taste it with 3 different small gins all from this region.
The front office staff from Silvia, Valentina and each person we interacted with have been amazing.
We were looking forward to the basset hounds as well, we have seen them lounging about but hope to get to meet them before our stay ends.
A wonderful place to stay in the Tuscan countryside, and only a 20 minute drive to Siena.
Reviewed on Jul 1, 2026
Top rated hotels for your Chianti Region vacation package

Hotel Toscana Ambassador
Via Salceto, 11 Poggibonsi SI
Free Cancellation
Reserve now, pay when you stay
11.49 mi from city center
$65 nightly
The price is $78 total per night
$78 total
Jul 13 - Jul 14
Total with taxes and fees
Hotel Toscana Ambassador features free WiFi in public areas, meeting rooms, and conference space. If you decide to drive, there's free parking. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Additional amenities include a business center, express check-in, and express check-out.
Parking included
Free WiFi

Castello Vicchiomaggio
Via Vicchiomaggio, 4 Greve in Chianti FI
Free Cancellation
Reserve now, pay when you stay
6.53 mi from city center
$139 nightly
The price is $153 total per night
$153 total
Jul 5 - Jul 6
Total with taxes and fees
Guests of Castello Vicchiomaggio enjoy features like a winery, free WiFi in public areas, and a seasonal outdoor pool. You can put free parking to good use if you drive. Front-desk staff can assist with tours/tickets and securing valuables. Additional amenities include a terrace, wedding services, and a banquet hall.
Pool
Parking included

Relais Villa Olmo
Via Imprunetana Per Tavarnuzze 19 Impruneta FI
Free Cancellation
Reserve now, pay when you stay
12.05 mi from city center
$192 nightly
The price is $214 total per night
$214 total
Jul 22 - Jul 23
Total with taxes and fees
Guests of Relais Villa Olmo enjoy access to a winery, a seasonal outdoor pool, and a terrace. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for EUR 185 per vehicle one-way. The front desk has multilingual staff that can help with securing valuables, tours or tickets, and dry cleaning/laundry. Other amenities at this golf residence include a picnic area, a banquet hall, and a garden.
Pool
Breakfast included
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.
Things to do

Small-Group Wine Tasting Experience in the Tuscan Countryside
$103
per adult
98% of travellers recommend

City Sightseeing Florence Hop-on Hop-off Bus Tour
$33
per adult
76% of travellers recommend

Florence Accademia Gallery Tour with Entrance Ticket Included
$55
per adult
92% of travellers recommend
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