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Montecastelli Vacations

Pack those stellar shades. We have Montecastelli vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Montecastelli – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Montecastelli vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Montecastelli

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Montecastelli vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Montecastelli well.

Montecastelli Flight + Hotel packages

Top Hotel Deals

See all 942 Hotels in Montecastelli
Relais Cappuccina Ristorante Hotel

Relais Cappuccina Ristorante Hotel

Loc La Cappuccina 46/a, San Gimignano
4.5 out of 5.0

This family-friendly San Gimignano hotel is located in a rural location, within 2 mi (3 km) of Sant'Agostino Church and Collegiate Church of Santa Maria Assunta. ...

$72

$72
Hotel Italia

Hotel Italia

Viale Camillo Benso Conte di Cavour, 67, Siena
3.5 out of 5.0

Located in the heart of Siena, this hotel is within 1 mi (2 km) of Stadio Artemio Franchi, University of Siena, and Museum of Torture. Piazza del Campo and Civic ...

$59

$59
Hotel Il Piccolo Castello

Hotel Il Piccolo Castello

Strada Provinciale Colligiana, 8, Monteriggioni
4.0 out of 5.0

This family-friendly Monteriggioni hotel is located in a rural location, 1.3 mi (2 km) from Monteriggioni Castle, and within 6 mi (10 km) of The Rock of Staggia ...

$66

$66
Hotel Leon Bianco

Hotel Leon Bianco

Piazza Della Cisterna 13, San Gimignano
3.0 out of 5.0

Located in Val d'Elsa, this hotel is steps from Piazza della Cisterna and Collegiate Church of Santa Maria Assunta. Medieval Criminal and Torture Museum and ...

$86

$86
Hotel Garden

Hotel Garden

Via Custoza 2, Siena
4.0 out of 5.0

Just outside the city walls near the Porta Camollia gate, this Siena hotel is about a 30-minute walk or 5-minute ride from the historic city centre, including ...

$60

$60
Palazzo San Lorenzo

Palazzo San Lorenzo

Via Gracco Del Secco 113, Colle di Val d'Elsa
4.5 out of 5.0

Located in Val d'Elsa, this spa hotel is within a 10-minute walk of Art in Color, Ranuccio Bianchi Bandinelli Archeological Museum, and Colle di Val d'Elsa Cathedral. ...

$110

$110
La Mormoraia

La Mormoraia

Agriturismo San Gimignano, San Gimignano

Located in Val d'Elsa, this farm stay is within 6 mi (10 km) of Sant'Agostino Church, Collegiate Church of Santa Maria Assunta, and Archaeological Museum - Spezieria ...

Hotel San Marco

Hotel San Marco

Strada Massetana, 70, Siena
3.5 out of 5.0

Situated in a shopping district, this spa hotel is within 2 mi (3 km) of Fontebranda, Palazzo Pubblico, and Piazza del Campo. Civic Museum and Stadio Artemio ...

$74

$74
Villasanpaolo

Villasanpaolo

Strada Provinciale Per Certaldo, San Gimignano
4.5 out of 5.0

Located in Val d'Elsa, this spa hotel is within 6 mi (10 km) of Sant'Agostino Church, Collegiate Church of Santa Maria Assunta, and Archaeological Museum - Spezieria ...

$158

$158
Le Volpaie

Le Volpaie

Via Nuova 9, San Gimignano
3.0 out of 5.0

Located in Castel San Gimignano, this hotel is within 9 mi (15 km) of Ornithological Museum, Museum San Gimignano 1300, and Piazza della Cisterna. Museum of ...