
Montecastelli Vacations
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Montecastelli Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Alfieri9
Historic Centre of Florence
$1,397
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Stay at this hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.
More quiet residential area of Firenze
in walking distance of center but away from the crowds. No elevator and two flight of stairs.
Reviewed on Jul 5, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World
Historic Centre of Florence
$4,645
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and room service. Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.

Corte Guelfa
Historic Centre of Florence
$1,530
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Stay at this residence in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Piazza del Duomo are located nearby.
The great location, kind service, and beautiful breakfasts! Our room was also ready early and they called drivers for us!
Reviewed on Aug 11, 2026

Il Malaspina
Historic Centre of Florence
$1,546
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this family-friendly hotel in Florence. Enjoy free breakfast, free WiFi, and 24-hour room service. Popular attractions Cathedral of Santa Maria del Fiore and Piazza del Duomo are located nearby.
Everything was great!
Reviewed on Aug 9, 2026

Il Rivalta - Place of Charme
Historic Centre of Florence
$1,859
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Stay at this apartment in Florence. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ponte Vecchio and Piazza della Signoria are located nearby.
The room was amazing! Like an apartment with the most amazing view! The front desk didn’t have anyone show us around the room and our keys wouldn’t work! The bellman tried and was most helpful but he couldn’t get it to work either. Breakfast was delicious however confusing on how to order. No signs or information provided. I’d stay again for the room, view and location and hope they work to address the little things that can make them 5 stars as the property and bellman is worth 5 stars
Reviewed on Aug 10, 2026

Bernini Palace
Historic Centre of Florence
$3,975
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Piazza della Signoria and Ponte Vecchio are located nearby.
Hotel Bernini Palace is truly a hidden gem in the heart of Florence’s historic city centre. The staff feel like family — anticipating your needs even before you ask. Breakfast was excellent, room service was great, and every visit has been memorable. The secret to their hospitality is simple: everyone, from the door assistant to the concierge, breakfast team, and cleaning staff, greets you with a genuine smile and real care. I’ve stayed here every time I’ve visited Florence, and I wouldn’t choose anywhere else. Truly outstanding hospitality, time and time again.”
Reviewed on Aug 11, 2026
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Hotel Toscana Ambassador
Via Salceto, 11 Poggibonsi SI
Book a stay at this business-friendly hotel in Poggibonsi. Enjoy free WiFi, free parking, and 24-hour room service. Our guests praise the helpful staff in our ...

Poderi Arcangelo
Localita Capezzano San Gimignano SI
Book a stay at this family-friendly farm stay in San Gimignano. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our ...

Villa Ermellina Siena, a Tribute Portfolio Hotel
Via Custoza 2 Siena SI
Book a stay at this family-friendly hotel in Siena. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...

Hotel Borgo San Luigi
STRADA DELLA CERRETA,7 Monteriggioni SI
Book a stay at this business-friendly hotel in Monteriggioni. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
Book a stay at this family-friendly hotel in San Gimignano. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...

Villa Sabolini
Loc. Mensanello Colle di Val d'Elsa SI
Stay at this hotel in Colle di Val d'Elsa. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Alta Val d'Elsa River Park and Le Caldane Thermal ...

Hotel Pescille by Double Hospitality
Strada Statale 47 San Gimignano SI
Stay at this hotel in San Gimignano. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Fattoria San Donato and Historical Torture Museum ...

Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Stay at this hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. ...

Borgo Pignano Volterra Tuscany
Localita Pignano 6 Volterra PI
Book a stay at this luxury farm stay in Volterra. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Castelvecchio and Castelvecchio ...

Hotel Il Piccolo Castello
Strada Provinciale Colligiana, 8 Monteriggioni SI
Stay at this hotel in Monteriggioni. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Monteriggioni Castle and Casa Vinicola Luigi Cecchi ...

Borgo Santo Pietro
Loc. Palazzetto Chiusdino SI
Book a stay at this luxury hotel in Chiusdino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di San Galgano and Eremo di Montesiepi ...

Hotel Sovestro
Localita Sovestro 63 San Gimignano SI
Book a stay at this golf hotel in San Gimignano. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...

Best Western Hotel San Marco
Strada Massetana 70 Siena SI
Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Piazza del Campo and Fisiocritici ...

Riparbella Country Suite
Località San Martino Riparbella PI
Stay at this hotel in Riparbella. Enjoy free WiFi, free parking, and a garden. Popular attractions La Regola Azienda Vitivinicola and Parco Avventura Il Giardino ...

Camping Boschetto Di Piemma
Localita' Santa Lucia 38C San Gimignano SI
Stay at this campground in San Gimignano. Enjoy free parking, 2 bars/lounges, and a garden. Popular attractions Sovestro in Poggio Winery and Tenuta Sovestro ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 12 - Sun, Aug 30
JFK
John F. Kennedy Intl.
FLR
Peretola
$748
Roundtrip
found 1 day ago

Thu, Aug 13 - Mon, Aug 31
JFK
John F. Kennedy Intl.
FLR
Peretola
$780
Roundtrip
found 1 day ago

Sun, Aug 30 - Tue, Sep 8
JFK
John F. Kennedy Intl.
FLR
Peretola
$892
Roundtrip
found 4 days ago

Wed, Sep 23 - Wed, Sep 30
JFK
John F. Kennedy Intl.
FLR
Peretola
$904
Roundtrip
found 6 days ago

Fri, Sep 25 - Sat, Oct 3
JFK
John F. Kennedy Intl.
FLR
Peretola
$960
Roundtrip
found 6 days ago
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