Montalcino Vacation Rentals from CA $145: Short-Term Rentals for 2026

Q: What's the top vacation rental that Montalcino has to offer?

Borgo Argiano : You might want to consider this vacation home rental near Montalcino, 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 kitchenware. You can relax into your vacation with a garden and a library. Another good choice for your trip to Montalcino is The House of Alice, charm and relaxation .

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Our top choices for Montalcino vacation rentals

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

1. B&B Le Scalette di Piazza

Montalcino

François

CA $204 total

includes taxes & fees

Oct 1 - Oct 2

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

2. Idolina Guest House

Montalcino

Bradley

CA $230 total

includes taxes & fees

Sep 23 - Sep 24

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

3. Palazzo Saloni

Montalcino

BRIAN

CA $560 total

includes taxes & fees

Sep 13 - Sep 14

A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

4. Corte Francigena - Apartments

Montalcino

Ryan

CA $255 total

includes taxes & fees

Oct 13 - Oct 14

An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

5. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

CA $225 total

includes taxes & fees

Sep 17 - Sep 18

A narrow street with outdoor seating, potted plants, and traditional buildings.

6. Room 'Camera Rossa' with Shared Terrace and Wi-Fi

Montalcino

Sam

CA $222 total

includes taxes & fees

Sep 13 - Sep 14

A terrace with a table set for tea, featuring a teapot, cups, and pastries. A clock tower is visible in the background.

7. Charming apartment in the historic center with large terrace and beautiful view

Montalcino

Marco R.

CA $278 total

includes taxes & fees

Sep 25 - Sep 26

An outdoor patio with tables and chairs, surrounded by greenery and a scenic view of hills and fields.

8. Podere Belsogno-apartment rose garden

Montalcino

"We stayed for six nights. Pros: clean, garden view is good. Cons: 1. When we are still sleeping at 10am, the staff unlock the door to come inside, it is so Scary. Lucky, we are still wearing clothes. 2. WiFi is unavailable. Staff do not reply message to solve. 3. Noisy at mid-nights ( TV sounds, lady laugh sounds, footsteps & refrigerator sounds) 4. The photo and description are misleading. There is not any bedroom. The photo is showed that the bedroom door is opening. In fact, the door...

Tsz Yeung

CA $222 total

includes taxes & fees

Sep 25 - Sep 26

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Top Montalcino Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"Excellent location. Easy parking and helpful staff."

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Find out more about Montalcino

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montalcino. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Montalcino?

Yes, you can find vacation rentals in Montalcino close to Bosco della Ragnaia, or you can choose a more secluded option if you're looking for a relaxing stay. Discover why Montalcino is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

What's the top vacation rental that Montalcino has to offer?

Borgo Argiano: You might want to consider this vacation home rental near Montalcino, 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 kitchenware. You can relax into your vacation with a garden and a library. Another good choice for your trip to Montalcino is The House of Alice, charm and relaxation.

How many vacation rentals are there in Montalcino?

With 32 Expedia vacation rentals, you're sure to find just the right place for your Montalcino stay.

What’s there to see and do in Montalcino?

Enjoy the outdoors at Val di Merse and Val di Chiana, or simply take in cultural attractions like Civic and Diocesan Museum of Sacred Art of Montalcino and Museum of Brunello. Other places in town to visit include Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi.

What’s a vacation rental in Montalcino like?

Vacation rentals are privately owned properties you can book for several days or longer in Montalcino. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Montalcino vacation rentals

1. B&B Le Scalette di Piazza

2. Idolina Guest House

3. Palazzo Saloni

4. Corte Francigena - Apartments

5. Podere Belsogno-camera Lavanda

6. Room 'Camera Rossa' with Shared Terrace and Wi-Fi

7. Charming apartment in the historic center with large terrace and beautiful view

8. Podere Belsogno-apartment rose garden

9. Divina Suite Montalcino & Wine Experience

10. Detached apartment

11. Bergamot with Garden

12. Anise with Terrace

13. Agritourism in val d'orcia

14. Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

15. A typical Tuscan country house

16. Apartment 'Casa Francesca' with Hills View & Courtyard

17. Il Borghetto - The House of Elba, rooftop panoramic terrace

18. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

19. Borgo Lucignanello Bandini

20. Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Find vacation rentals that suit your style

Top Montalcino Hotel Reviews

Hotel Chiusarelli

Hotel Athena

NH Siena

Drogheria & Locanda Franci

Castello di Velona Resort Thermal SPA & Winery

Podere Brizio

La Certosa di Pontignano

Capanna Suites

SI Montalcino Hotel

Find out more about Montalcino

Frequently asked questions

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