Montechiaro Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Montechiaro vacation rentals

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
$141 nightly
The price is $159
Jan 4 - Jan 5, 2026
Total with taxes and fees
Siena Vip

Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
$81 nightly
The price is $94
Jan 15 - Jan 16, 2026
Total with taxes and fees
Al Mercato B&B

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (194)
"Great location and friendly staff. "
United States
Parissa
$152 nightly
The price is $172
Dec 29 - Dec 30
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
Domus il Palio B&B

B&B Dei Rossi

B&B Dei Rossi
Siena City Centre
8.2 out of 10, Very Good, (18)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
$73 nightly
The price is $86
Jan 26 - Jan 27, 2026
Total with taxes and fees
B&B Dei Rossi

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (49)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$106 nightly
The price is $122
Jan 10 - Jan 11, 2026
Total with taxes and fees
Fullino Nero

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Palazzo Masi

Palazzo Masi
Siena City Centre
8.8 out of 10, Excellent, (84)
"Very friendly and attentive, a very clean place and its location is excellent. "
United States
Gloria
$96 nightly
The price is $111
Jan 2 - Jan 3, 2026
Total with taxes and fees
Palazzo Masi

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
$101 nightly
The price is $114
Jan 11 - Jan 12, 2026
Total with taxes and fees
DormiVeglia B&B

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
$61 nightly
The price is $72
Jan 18 - Jan 19, 2026
Total with taxes and fees
ApartHotel Anghel

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
$96 nightly
The price is $111
Jan 6 - Jan 7, 2026
Total with taxes and fees
B&B Il Corso

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$84 nightly
The price is $96
Jan 7 - Jan 8, 2026
Total with taxes and fees
Tuscasì Aparthotel

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
$107 nightly
The price is $123
Jan 7 - Jan 8, 2026
Total with taxes and fees
La Coroncina Lodging

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
$171 nightly
The price is $193
Jan 27 - Jan 28, 2026
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8)
"Personal people are very good. "
Switzerland
Wenjuan
$91 nightly
The price is $105
Dec 28 - Dec 29
Total with taxes and fees
Villa le Camelie Siena

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
$91 nightly
The price is $104
Jan 22 - Jan 23, 2026
Total with taxes and fees
Casa di Campagna in Toscana
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Montechiaro Hotel Reviews

Find out more about Montechiaro

Everything you need to know about Montechiaro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montechiaro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montechiaro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montechiaro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montechiaro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montechiaro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montechiaro rentals

At Expedia, we put the best Montechiaro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montechiaro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montechiaro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montechiaro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Montechiaro?

Yes, we have vacation rentals close to well known attractions in Montechiaro, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Montechiaro has to offer?

Borgo Argiano: Visitors like this Montechiaro vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

What’s there to see and do in Montechiaro?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Chianti Sculpture Park. In the larger area, you’ll find Porta Romana and Siena State Archives.

What’s a vacation rental in Montechiaro like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Montechiaro. Vacation rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.