Montecastelli Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
27.6 km from city center
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 ...
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

3 out of 5
Loc. San Donato San Gimignano SI
19.64 km from city center
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. ...
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
29.33 km from city center
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

Villa Ermellina Siena, a Tribute Portfolio Hotel

4 out of 5
Via Custoza 2 Siena SI
29.62 km from city center
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

Hotel Borgo San Luigi

4 out of 5
STRADA DELLA CERRETA,7 Monteriggioni SI
21.38 km from city center
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 Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
30.16 km from city center
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. ...
Villa Sabolini

Villa Sabolini

4 out of 5
Loc. Mensanello Colle di Val d'Elsa SI
18.24 km from city center
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 ...
Borgo Pignano Volterra Tuscany

Borgo Pignano Volterra Tuscany

5 out of 5
Localita Pignano 6 Volterra PI
16.54 km from city center
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 Pescille by Double Hospitality

Hotel Pescille by Double Hospitality

3 out of 5
Strada Statale 47 San Gimignano SI
20.92 km from city center
Stay at this hotel in San Gimignano. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tenuta Torciano Winery and Fattoria San Donato are ...
Hotel Il Piccolo Castello

Hotel Il Piccolo Castello

4 out of 5
Strada Provinciale Colligiana, 8 Monteriggioni SI
24.61 km from city center
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

Borgo Santo Pietro

5 out of 5
Loc. Palazzetto Chiusdino SI
19.62 km from city center
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

Hotel Sovestro

3 out of 5
Localita Sovestro 63 San Gimignano SI
23.02 km from city center
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 ...
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3 out of 5
Localita' Santa Lucia 38C San Gimignano SI
22.17 km from city center
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 ...
Riparbella Country Suite

Riparbella Country Suite

Località San Martino Riparbella PI
31.16 km from city center
Stay at this hotel in Riparbella. Enjoy free breakfast, free WiFi, and free parking. Popular attractions La Regola Azienda Vitivinicola and Parco Avventura Il ...
Mormoraia

Mormoraia

Agriturismo San Gimignano San Gimignano SI
27.23 km from city center
Book a stay at this luxury farm stay in San Gimignano. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Don't see what you're looking for?
See all available properties in Montecastelli
View all properties
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.

Delta
Sun, Aug 9 - Wed, Aug 26
JFK
John F. Kennedy Intl.
FLR
Peretola
$665 Roundtrip, found 2 days ago
$665
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Aug 9 from John F. Kennedy Intl. to Peretola, returning Wed, Aug 26, priced at $665 found 2 days ago
TAP Portugal
Wed, Sep 23 - Wed, Sep 30
JFK
John F. Kennedy Intl.
FLR
Peretola
$701 Roundtrip, found 3 days ago
$701
Roundtrip
found 3 days ago
Select TAP Portugal flight, departing Wed, Sep 23 from John F. Kennedy Intl. to Peretola, returning Wed, Sep 30, priced at $701 found 3 days ago
Scandinavian Airlines
Tue, Aug 25 - Tue, Sep 8
JFK
John F. Kennedy Intl.
FLR
Peretola
$701 Roundtrip, found 1 day ago
$701
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Tue, Aug 25 from John F. Kennedy Intl. to Peretola, returning Tue, Sep 8, priced at $701 found 1 day ago
Air France
Mon, Aug 10 - Thu, Aug 27
JFK
John F. Kennedy Intl.
FLR
Peretola
$703 Roundtrip, found 2 days ago
$703
Roundtrip
found 2 days ago
Select Air France flight, departing Mon, Aug 10 from John F. Kennedy Intl. to Peretola, returning Thu, Aug 27, priced at $703 found 2 days ago
Swiss International Air Lines
Tue, Aug 11 - Fri, Aug 21
JFK
John F. Kennedy Intl.
FLR
Peretola
$711 Roundtrip, found 6 days ago
$711
Roundtrip
found 6 days ago
Select Swiss International Air Lines flight, departing Tue, Aug 11 from John F. Kennedy Intl. to Peretola, returning Fri, Aug 21, priced at $711 found 6 days ago