Montechiaro Vacation Rentals from $95: Search Short-Term Rentals

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

Borgo Argiano : You might want to consider this vacation home rental near Montechiaro, which 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.

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Our top choices for Montechiaro vacation rentals

Riserva di Fizzano Residence

Castellina in Chianti

Janet

$227 nightly

Jul 2 - Jul 3

Total with taxes and fees

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Castelnuovo Berardenga

Jeremy

$155 nightly

Jul 10 - Jul 11

Total with taxes and fees

Residence Arianna

Sovicille

"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...

Gitte Harrits

$124 nightly

Jul 2 - Jul 3

Total with taxes and fees

Sportland

Colle di Val d'Elsa

Giorgio

$47 nightly

Jun 28 - Jun 29

Total with taxes and fees

Palazzo Pacini

Colle di Val d'Elsa

John

$152 nightly

Jun 29 - Jun 30

Total with taxes and fees

Borgo di Erboli

Cavriglia

$99 nightly

Jul 16 - Jul 17

Total with taxes and fees

Bosco della Spina

Murlo

Lizl

$139 nightly

Jun 28 - Jun 29

Total with taxes and fees

Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

$295 nightly

Jun 28 - Jun 29

Total with taxes and fees

Borgo Argenina

Gaiole in Chianti

Sasha

$390 nightly

Jul 3 - Jul 4

Total with taxes and fees

Villa Mucellena

Casole d'Elsa

$113 nightly

Jul 5 - Jul 6

Total with taxes and fees

Casa di Campagna in Toscana

Sovicille

Sally

$119 nightly

Jun 28 - Jun 29

Total with taxes and fees

Villa San Filippo

Barberino Tavarnelle

ALEXANDER

$81 nightly

Jul 2 - Jul 3

Total with taxes and fees

Castello di Gargonza

Monte San Savino

Ariel

$272 nightly

Jul 3 - Jul 4

Total with taxes and fees

Siena Vip

Siena City Centre

David

$113 nightly

Jun 30 - Jul 1

Total with taxes and fees

Borgo Lucignanello Bandini

Montalcino

Marc

$362 nightly

Jun 29 - Jun 30

Total with taxes and fees

Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

Siena City Centre

Margaret

$114 nightly

Jul 15 - Jul 16

Total with taxes and fees

Villa Curina Resort

Castelnuovo Berardenga

Dr Anne

$164 nightly

Jun 28 - Jun 29

Total with taxes and fees

Il Pozzo di Sant'Andrea

Siena

Prem

$105 nightly

Jun 30 - Jul 1

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, individually furnished

Tuscasì Aparthotel

Sovicille

Sergey

$83 nightly

Jul 3 - Jul 4

Total with taxes and fees

Ca' Bianca Tuscany Relais

Siena

Talha

$295 nightly

Jun 30 - Jul 1

Total with taxes and fees

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Top Montechiaro Hotel Reviews

Hotel Toscana Ambassador

10/10 Excellent

"Room was clean, staff was helpful and easy to park."

Hotel Italia

10/10 Excellent

"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the A/C worked perfectly; we didn’t hear a sound from neighbors or stair traffic. The location is a sweet spot — only 5 to 10 minutes from the tourist sights, yet tucked in a local neighborhood with bakeries and grocery stores, giving us that refreshing, peaceful feeling of being disconnected from the tourist rush. Breakfast was amazing, and the little teen-approved Duomo and gelato challenges made exploring even more fun. Bottom line: we’d come back and stay here again in a heartbeat. For anyone visiting Siena, Hotel Italia at Porta Camollia gives you that perfect “live like a local” buffer before diving into the Duomo and Piazza del Campo — and if you need a salon, just ask reception; their pick is solid."

Relais Vignale & Spa

10/10 Excellent

"We had a wonderful stay at Relais Vignale! Our room was wonderful and we had a beautiful terrace. The breakfast was lovely and included and the pool was relaxing. We also used the spa for a morning which we loved before the winery tour we booked through the resort. It made the trip so easy and relaxing and it was nice to cross the street to Dante’s for food and wine and walk around the beautiful little town of Radda. Highly recommend!!"

Palazzo Ravizza

10/10 Excellent

"This hotel needs another star!!! It is absolutely wonderful. The rooms are spacious, beautiful, and well supplied. The bathroom is luxurious. The staff is helpful and friendly. The breakfast is delicious and the garden is relaxing and fresh with turtles that come up and say hi while you dine. There is a library where you can take books and trade them with ones you have read. I will stay here again next time I come to Siena."

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good

"The hotel and grounds were beautiful, however we weren’t aware there were multiple buildings on the property and were given a dark room on the ground floor of a back building. We had also booked the junior suite but our room, while large, did not have a couch as described."

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 $95 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: You might want to consider this vacation home rental near Montechiaro, which 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.

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Check prices for these dates

Our top choices for Montechiaro vacation rentals

Riserva di Fizzano Residence

Villa di Sotto

Residence Arianna

Sportland

Palazzo Pacini

Borgo di Erboli

Bosco della Spina

Terre di Baccio

Borgo Argenina

Villa Mucellena

Casa di Campagna in Toscana

Villa San Filippo

Castello di Gargonza

Siena Vip

Borgo Lucignanello Bandini

La Terrazza Sul Campo Rooming House

Villa Curina Resort

Il Pozzo di Sant'Andrea

Tuscasì Aparthotel

Ca' Bianca Tuscany Relais

Find vacation rentals that suit your style

Top Montechiaro Hotel Reviews

Hotel Toscana Ambassador

Hotel Italia

Hotel Minerva

Relais Vignale & Spa

Villa Scacciapensieri Boutique Hotel

Borgo Scopeto Wine & Country Relais

Palazzo Ravizza

Hotel Chiusarelli

Villa Ermellina Siena, a Tribute Portfolio Hotel

Find out more about Montechiaro

Frequently asked questions

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