Montegrossi Vacation Rentals from CA $69: Short-Term Rentals for 2026

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.

Check prices for these dates

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Our top choices for Montegrossi vacation rentals

A stone building with a garden in front.

1. Borgo Argenina

Gaiole in Chianti

Tatevik

CA $278 total

includes taxes & fees

Oct 27 - Oct 28

A villa with a swimming pool, outdoor seating, and a tennis court.

2. Villa Curina Resort

Castelnuovo Berardenga

Deanna

CA $229 total

includes taxes & fees

Oct 23 - Oct 24

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

3. Villa di Sotto

Castelnuovo Berardenga

Philippe

CA $260 total

includes taxes & fees

Oct 21 - Oct 22

A stone building with a yellow sign reading "b&b erioico".

4. L' Eroico

Gaiole in Chianti

Angela

CA $209 total

includes taxes & fees

Nov 5 - Nov 6

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

5. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

CA $219 total

includes taxes & fees

Oct 29 - Oct 30

A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

6. Residenzia del Sogno

Castellina in Chianti

Katherine

CA $212 total

includes taxes & fees

Oct 30 - Oct 31

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

7. Mariani Bed & Breakfast

Castellina in Chianti

Frank

CA $137 total

includes taxes & fees

Oct 27 - Oct 28

A stone building with multiple windows and a chimney.

8. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $205 total

includes taxes & fees

Nov 8 - Nov 9

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

9. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

CA $189 total

includes taxes & fees

Nov 16 - Nov 17

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

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

CA $251 total

includes taxes & fees

Oct 21 - Oct 22

A cozy living room with a stone wall, a wine rack, and two sofas.

11. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

CA $179 total

includes taxes & fees

Oct 27 - Oct 28

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

12. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

CA $146 total

includes taxes & fees

Oct 23 - Oct 24

A table with breakfast items and a view of rolling hills.

13. Chianti Village Morrocco

Tavarnelle Val di Pesa

Winonah

CA $133 total

includes taxes & fees

Nov 20 - Nov 21

A rustic stone building with a courtyard.

14. Fullino Nero

Siena

Annie

CA $157 total

includes taxes & fees

Oct 27 - Oct 28

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

15. Terre di Baccio

Greve in Chianti

Gage

CA $454 total

includes taxes & fees

Oct 31 - Nov 1

An arched stone bridge with a white building on the right, featuring a balcony with plants.

16. Locanda Antico Borgo

Civitella in Val di Chiana

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

Mr Andy

CA $161 total

includes taxes & fees

Oct 30 - Oct 31

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

17. Castello di Gargonza

Monte San Savino

Iain

CA $382 total

includes taxes & fees

Oct 21 - Oct 22

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

18. ApartHotel Anghel

Siena

Lauro

CA $104 total

includes taxes & fees

Nov 15 - Nov 16

A table set with various items including a book, glassware, and decorative objects against a stone wall backdrop.

19. 'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

Gaiole in Chianti

Mariah M.

CA $563 total

includes taxes & fees

Oct 31 - Nov 1

A bedroom with a bed, bedside table, and a window with a view of greenery.

20. La Coroncina Lodging

Siena

Hassan

CA $171 total

includes taxes & fees

Nov 9 - Nov 10

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Top Montegrossi Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good

"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."

Il Chiostro del Carmine

8/10 Good

"We really enjoyed our stay at Il Chiostro del Carmine. The hotel is definitely a little older, but that was part of the charm for us. Staying inside a former monastery gave the property so much character and made it feel completely different from a typical hotel. The location was also excellent. It sits just outside the busiest part of Siena, but we were still within about a 10-minute walk of pretty much everything we wanted to see or do. The atmosphere was peaceful, the setting was unique, and it fit Siena perfectly. If you prefer hotels with history and character over ultra-modern ones, this is a great place to stay."

Fattoria di Vegi

10/10 Excellent

"We loved our stay here! It was the perfect place to slow down and take in the beauty of Tuscany. We enjoyed the cooking class and wine tasting we took with the other couples staying there. Highly recommend booking this as part of your stay! We also enjoyed the amenities they offered like the art room - we set up easels in the grass, drank wine, and drew each other’s portraits which ended up being pretty funny. The food at the restaurant was good although it felt like some of the dishes could’ve been simpler. Our favorite dishes was the pasta with mushrooms and the pizzas on pizza night. The majority of the staff was friendly too. Highly recommend this location if you’re looking for a beautifully designed, relaxing location with amenities/activities. We hope to be back!"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montegrossi vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montegrossi vacation rentals we have selected for you start as low as CA $69 per night. Entering your travel dates in the search wizard 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. Borgo Argenina

2. Villa Curina Resort

3. Villa di Sotto

4. L' Eroico

5. Relais Villa Belpoggio - Residenza d'Epoca

6. Residenzia del Sogno

7. Mariani Bed & Breakfast

8. Agriturismo La Ferrozzola

9. Casa Vacanze Squarcialupi

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

11. Villa Cassia di Baccano

12. Relais Villa Belvedere

13. Chianti Village Morrocco

14. Fullino Nero

15. Terre di Baccio

16. Locanda Antico Borgo

17. Castello di Gargonza

18. ApartHotel Anghel

19. 'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

20. La Coroncina Lodging

Find vacation rentals that suit your style

Top Montegrossi Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

La Certosa di Pontignano

Il Chiostro del Carmine

Fattoria di Vegi

Piccolo Hotel Etruria

Hotel Chiusarelli

Hotel Italia

Castello di Spaltenna- Small Luxury Hotels of the World

Four Points by Sheraton Siena

Find out more about Montegrossi

Frequently asked questions

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