Montegrossi Vacation Rentals from $62: 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

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

1. L' Eroico

Gaiole in Chianti

Angela

$128 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

2. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

$68 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Ruffoli

"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...

Michael F.

$165 nightly

Nov 9 - Nov 10

Total with taxes and fees

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

4. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

$128 nightly

Dec 4 - Dec 5

Total with taxes and fees

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

Kristina

$159 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

6. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

$118 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

7. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

$99 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

8. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

$95 nightly

Nov 24 - Nov 25

Total with taxes and fees

A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

9. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Figline Valdarno

$118 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

10. ApartHotel Anghel

Siena

clifford

$52 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

11. Tuscasì Aparthotel

Sovicille

Sergey

$73 nightly

Nov 20 - Nov 21

Total with taxes and fees

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

12. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

$107 nightly

Dec 1 - Dec 2

Total with taxes and fees

A rustic stone building with a courtyard.

13. Fullino Nero

Siena

Annie

$101 nightly

Nov 10 - Nov 11

Total with taxes and fees

An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

14. Guild Living Siena Senior Resort & Residence

Scacciapensieri

"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."

Heidi

$97 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

15. 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

$101 nightly

Nov 14 - Nov 15

Total with taxes and fees

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

16. Villa Fontis Rapolano

Rapolano Terme

Barbara

$85 nightly

Nov 11 - Nov 12

Total with taxes and fees

A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.

17. Old medieval apartment

Tavarnelle Val di Pesa

Kathleen F.

$124 nightly

Nov 9 - Nov 10

Total with taxes and fees

A dining area with a table set for two, featuring a view of greenery through a window.

18. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

$144 nightly

Nov 9 - Nov 10

Total with taxes and fees

A stone building with a sloped roof, a small porch, and a gravel driveway.

19. Podere La Chiusella

Rapolano Terme

"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...

Kevin

$94 nightly

Nov 15 - Nov 16

Total with taxes and fees

A table with two wine glasses, a bottle, and a book.

20. Domus il Palio B&B

Ravacciano

Leo

$66 nightly

Nov 18 - Nov 19

Total with taxes and fees

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Top Montegrossi Hotel Reviews

La Certosa di Pontignano - Place of Charme

10/10 Excellent

"Endroit magnifique et bien situé pour visiter la région."

Il Chiostro del Carmine

8/10 Good

"The location was excellent, within walking distance to all the sights but far enough that it was quiet. Breakfast was excellent and if you can get window seating, it will make a perfect start of the day. The staff was helpful but remains in the background unless you need something. The room was clean, only caveat is the shower is rather small for such a big bathroom. We will stay here again."

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay 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 $62 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.

Room 1

Check prices for these dates

Our top choices for Montegrossi vacation rentals

1. L' Eroico

2. Chianti Village Morrocco

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

4. Agriturismo La Ferrozzola

5. Relais Villa Belpoggio - Residenza d'Epoca

6. Casa Vacanze Squarcialupi

7. Relais Villa Belvedere

8. Villa Cassia di Baccano

9. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

10. ApartHotel Anghel

11. Tuscasì Aparthotel

12. Antica Pieve B&B

13. Fullino Nero

14. Guild Living Siena Senior Resort & Residence

15. Locanda Antico Borgo

16. Villa Fontis Rapolano

17. Old medieval apartment

18. La Locanda di Pietracupa

19. Podere La Chiusella

20. Domus il Palio B&B

Find vacation rentals that suit your style

Top Montegrossi Hotel Reviews

La Certosa di Pontignano - Place of Charme

Salvadonica - Borgo del Chianti

Il Chiostro del Carmine

Dievole Wine Resort

Borgo Grondaie

Hotel Borgo San Luigi

Hotel Chiusarelli

Hotel Italia

Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Montegrossi

Frequently asked questions