Montegrossi Vacation Rentals from $69: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Montegrossi?

Borgo Argiano : This vacation home rental outside of Montegrossi 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.

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Our top choices for Montegrossi vacation rentals

1. L' Eroico

Gaiole in Chianti

Angela

$153 nightly

Oct 21 - Oct 22

Total with taxes and fees

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

2. Borgo di Erboli

Cavriglia

Luca

$87 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

3. Villa di Sotto

Castelnuovo Berardenga

Philippe

$159 nightly

Sep 21 - Sep 22

Total with taxes and fees

4. Borgo Argenina

Gaiole in Chianti

Tatevik

$193 nightly

Sep 22 - Sep 23

Total with taxes and fees

5. Villa Curina Resort

Castelnuovo Berardenga

Joe

$155 nightly

Sep 27 - Sep 28

Total with taxes and fees

6. Mariani Bed & Breakfast

Castellina in Chianti

Chie

$89 nightly

Oct 7 - Oct 8

Total with taxes and fees

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

7. Residenzia del Sogno

Castellina in Chianti

Katherine

$125 nightly

Sep 21 - Sep 22

Total with taxes and fees

8. Villa Rosa Panzano

Greve in Chianti

Allison

$125 nightly

Oct 4 - Oct 5

Total with taxes and fees

9. Domus il Palio B&B

Ravacciano

Alissia

$62 nightly

Oct 14 - Oct 15

Total with taxes and fees

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

$175 nightly

Sep 22 - Sep 23

Total with taxes and fees

11. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

$146 nightly

Oct 14 - Oct 15

Total with taxes and fees

12. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

$169 nightly

Sep 29 - Sep 30

Total with taxes and fees

13. Chianti Village Morrocco

Tavarnelle Val di Pesa

Chris

$74 nightly

Oct 15 - Oct 16

Total with taxes and fees

Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

14. Podere Vesta

Asciano

Katerine

15. Camping Village Il Poggetto.

Rignano sull'Arno

Alex

$59 nightly

Sep 21 - Sep 22

Total with taxes and fees

Studio, Patio, Ground Floor | Terrace/patio

16. Fullino Nero

Siena

Christian

$99 nightly

Sep 27 - Sep 28

Total with taxes and fees

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

17. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

$97 nightly

Oct 17 - Oct 18

Total with taxes and fees

18. Villa Fontis Rapolano

Rapolano Terme

Barbara

$83 nightly

Sep 22 - Sep 23

Total with taxes and fees

19. Villa San Filippo

Barberino Val d'Elsa

Nadia

$99 nightly

Sep 23 - Sep 24

Total with taxes and fees

20. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

$133 nightly

Oct 21 - Oct 22

Total with taxes and fees

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Top Montegrossi Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

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Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This resort was simply beautiful! We stayed in the grand room as there were 5 of us, and it was much bigger than I expected! Three bedrooms, 3 washrooms, huge living room - it was great! As we had 2 kids, we had to use the family pool, which was conveniently close to our room. No bar at the pool, but there was a QR code to order drinks and food. There were towels at the pool as well. The staff were very kind and helpful. We appreciated the welcome gift of wine, juice, and snacks too! The breakfast buffet was lovely with lots of variety of hot and cold items. Would highly recommend this resort."

Fattoria di Vegi

10/10 Excellent

"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks were also brilliant - best meal we had in Tuscany was in the hotel. My only suggestions would be to rotate the staff more - they seemed slightly over worked. Easily one of the best hotels I have stayed in."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Palazzo Ravizza

10/10 Excellent

"We had a wonderful time at this hotel. Everything was excellent and everyone so helpful. Great room ,that had a wonderful view of the gardens . The room was very clean and well equipt with all you need to enjoy your stay. Walkable access to the centre with some lovely shops ,bars and restaurants on the way. A massive thank you to Francesca who was brilliant. So knowledgable about the area and friendly and helpful. Her and the team are doing a wonderful job. Would highly recommend and I would visit again."

Find out more about Montegrossi

Everything you need to know about Montegrossi 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 Montegrossi 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 Montegrossi vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montegrossi vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montegrossi. 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 Montegrossi 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 $69 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 Montegrossi rentals

At Expedia, we put the best Montegrossi 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 Montegrossi 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 Montegrossi 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 Montegrossi. 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 Montegrossi?

Yes, there are vacation rentals close to well known sights in Montegrossi, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Montegrossi?

Borgo Argiano: This vacation home rental outside of Montegrossi 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.

What’s there to see and do in Montegrossi?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Terme Antica Querciolaia. Badia a Coltibuono and Meleto Castle are a couple of places you'll find in the larger area.

What’s a vacation rental in Montegrossi like?

Vacation rentals are private properties you can stay in for short or long periods in Montegrossi. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.

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Check prices for these dates

Our top choices for Montegrossi vacation rentals

1. L' Eroico

2. Borgo di Erboli

3. Villa di Sotto

4. Borgo Argenina

5. Villa Curina Resort

6. Mariani Bed & Breakfast

7. Residenzia del Sogno

8. Villa Rosa Panzano

9. Domus il Palio B&B

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

11. Relais Villa Belpoggio - Residenza d'Epoca

12. Villa Cassia di Baccano

13. Chianti Village Morrocco

14. Podere Vesta

15. Camping Village Il Poggetto.

16. Fullino Nero

17. Relais Villa Belvedere

18. Villa Fontis Rapolano

19. Villa San Filippo

20. Casa Vacanze Squarcialupi

Find vacation rentals that suit your style

Top Montegrossi Hotel Reviews

Hotel Chiusarelli

NH Siena

Borgo Scopeto Wine & Country Relais

Villa Scacciapensieri Boutique Hotel

Fattoria di Vegi

La Certosa di Pontignano

Grand Hotel Continental Siena – Starhotels Collezione

Palazzo Ravizza

Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Montegrossi

Frequently asked questions

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