$229 Cheap flights to Province of Siena
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Top places to visit in Province of Siena
Cheap flights to Province of Siena from $229 One Way, $190 Round Trip
$190 return flights and $229 one-way flights to Province of Siena were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JFK
New York
FLR
Florence
$320 Roundtrip, found 1 day ago
$320
Roundtrip
found 1 day ago
BOS
Boston
FLR
Florence
$382 Roundtrip, found 13 hours ago
$382
Roundtrip
found 13 hours ago
BOS
Boston
PSA
Pisa
$420 Roundtrip, found 3 days ago
$420
Roundtrip
found 3 days ago
IAD
Washington
FLR
Florence
$471 Roundtrip, found 1 hour ago
$471
Roundtrip
found 1 hour ago
JFK
New York
PSA
Pisa
$475 Roundtrip, found 22 hours ago
$475
Roundtrip
found 22 hours ago
MIA
Miami
PSA
Pisa
$488 Roundtrip, found 3 days ago
$488
Roundtrip
found 3 days ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LHR | Pisa | December 27 to January 8 | $190 |
| CDG | Florence | December 28 to January 4 | $337 |
| AMS | Florence | December 27 to January 29 | $345 |
| LGW | Florence | December 27 to December 29 | $366 |
| BCN | Florence | December 26 to December 27 | $439 |
| JFK | Florence | December 27 to January 13 | $450 |
| AMS | Pisa | December 28 to December 30 | $1,304 |
| JFK | Pisa | December 28 to January 6 | $1,797 |
Find The Perfect Hotel For After Your Flight
Score Epic Province of Siena Accommodation Deals
Il Chiostro del Carmine
Via Della Diana 4 Siena SI
Fully refundableReserve now, pay when you stay
Stay at this B&B in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Fisiocritici ...
8.6/10 Excellent! (854 reviews)
Terrific place to stay. Breakfast was great, staff were friendly, and the view we had was stunning. Lots of room Old monastery was very interesting.
Reviewed on Nov 3, 2025
La Perla
Via Delle Terme 25 Siena SI
$69 nightly
The price is $79 total per night from Jan 6 to Jan 7
$79 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Stay at this hotel in Siena. Enjoy free WiFi, daily housekeeping, and pillowtop beds. Popular attractions Teatro dei Rozzi and Loggia della Mercanzia are located ...
7.6/10 Good! (284 reviews)
Clean, great location - covers all the basics for a good price.
Reviewed on Nov 13, 2025
Sangallo Park Hotel
Strada Di Vico Alto 2 Siena SI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Jan 6 to Jan 7
$102 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Casalvento's Wines and Palasport ...
9/10 Wonderful! (575 reviews)
Practical and close enough to the city. You still need a car to go to Siena
Reviewed on Oct 27, 2025
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Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $76 total per night from Jan 11 to Jan 12
$76 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
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. ...
9/10 Wonderful! (981 reviews)
This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended
Reviewed on Dec 4, 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.
Our Top Province of Siena Apartment Hotels
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Montepulciano Siena
Stay at this vacation home in Montepulciano. Enjoy a garden, laundry facilities, and patios. Popular attractions Medici Fortress and Torre del Pulcinella are ...
9.4/10 Exceptional! (62 reviews)
We had a great stay at this house. Enough room for everyone and the amenities were as described. It was a bit of a walk along a road to get to the main section of town but close enough to be reasonably convenient. The parking spot was very helpful. We visited in mid November and many of the businesses ...
Reviewed on Nov 29, 2025
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Fonti Medievali and Archaeological ...
10/10 Exceptional! (71 reviews)
The property is beautiful and very well taken care of. Loved the location and how wonderful the owners were to help with organizing drivers, chef, and other needs. Would highly recommend and will definitely be back. Very special experience.
Reviewed on Oct 26, 2025
Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi
CASTELNUOVO BERARDENGA Tuscany
Book a stay at this family-friendly villa in Castelnuovo Berardenga. Enjoy free WiFi, private pools, and a fitness center. Popular attractions San Felice Winery ...
10/10 Exceptional! (23 reviews)
Wonderful experience for our family of four in this delightful, large, fully restored Tuscany villa. This is part of Arceno properties a highly professional company that manages several properties in the area and takes care of all the details. This seems to be their more luxurious villa. It is set ...
Reviewed on Aug 15, 2025
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Farmhouse in the heart of the real chiantishire
Castellina in Chianti Tuscany
Stay at this vacation home in Castellina in Chianti. Enjoy a garden, laundry facilities, and patios. Popular attractions Casa Vinicola Luigi Cecchi and Castellina ...
9.8/10 Exceptional! (101 reviews)
Daniele was very welcoming and informative. Sent us a list of things to do, where to sightsee, which wineries and restaurants he recommended. View from the rear terrace was spectacular.
Reviewed on Nov 17, 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.
Score Epic Province of Siena Accommodation Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is $100 total per night from Jan 8 to Jan 9
$100 total
per night
Jan 8 - Jan 9
Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,007 reviews)
Great location, very friendly staff
Reviewed on Dec 13, 2025
Borgo Grondaie
Strada delle Grondaie, 15 Siena SI
Stay at this hotel in Siena. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Porta ...
9.6/10 Exceptional! (439 reviews)
The sta
Reviewed on Nov 17, 2025
Palazzo Ravizza
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
The price is $117 total per night from Dec 21 to Dec 22
$117 total
per night
Dec 21 - Dec 22
Stay at this hotel in Siena. Enjoy free WiFi, room service, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (746 reviews)
Ideal in every way.
Reviewed on Dec 2, 2025
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Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
The price is $312 total per night from Dec 22 to Dec 23
$312 total
per night
Dec 22 - Dec 23
Book a stay at this luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (571 reviews)
The Grand Hotel Continental in Siena is a rare gem,elegant, inviting, and steeped in history. From the beautifully preserved interiors to the warm, attentive staff, every detail makes you feel genuinely cared for. Its central location is unbeatable, placing Siena’s most charming sights just steps ...
Reviewed on Nov 20, 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.
Family Friendly Hotels in Province of Siena
Piazza Paradiso Accomodation
Via di Stalloreggi, 38 Siena SI
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly affittacamere in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Pinacoteca Nazionale ...
9.2/10 Wonderful! (151 reviews)
What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza ...
Reviewed on Oct 12, 2025
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Fonti Medievali and Archaeological ...
10/10 Exceptional! (71 reviews)
Families like: Private pool, kitchen, playground, game room
Travelers say...
The property is beautiful and very well taken care of. Loved the location and how wonderful the owners were to help with organizing drivers, chef, and other needs. Would highly recommend and will definitely be back. Very special experience.
Reviewed on Oct 26, 2025
Hotel La Terrazza di Montepulciano
Via Pié al Sasso 16 Montepulciano SI
The price is $133 total per night from Dec 23 to Dec 24
$133 total
per night
Dec 23 - Dec 24
Stay at this hotel in Montepulciano. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Civic Museum and Palazzo Ricci are located ...
9.2/10 Wonderful! (195 reviews)
Perfect location - could walk everywhere. Roberto and his wife were incredible hosts. They treated us like family. They served us a delicious breakfast, gave us information about restaurants and wine tastings, provided help with transportation. We hope to return soon. This place is a gem. The hosts ...
Reviewed on Nov 20, 2025
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La Terrazza Sul Campo Rooming House
Via di Città 65 Siena SI
Stay at this residence in Siena. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Museum of Torture and Palazzo Chigi-Saracini are ...
9.6/10 Exceptional! (239 reviews)
Beyond what we expected
The room we were assigned was immense. The views from the 2 double french doors was amazing - in the corner of the piazza right next to the tower. The bed was very comfortable and the bathroom quite modern and spacious. The room must be used for parties orother events as it was much much larger than ...
Reviewed on Oct 25, 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.
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Province of Siena
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.