Title: Montemassi Vacation Packages & Trips 2026 from CA $2,126 | Expedia.ca

[Hotels in Montemassi](https://expedia.ca/Montemassi-Hotels.d6361379.Travel-Guide-Hotels)[Vacation Rentals in Montemassi](https://expedia.ca/Montemassi-Vacation-Rentals.d6361379.Travel-Guide-VacationRentals)[Things to do in Montemassi](https://expedia.ca/Things-To-Do-In-Montemassi.d6361379.Travel-Guide-Activities)[Montemassi Car Rentals](https://expedia.ca/Car-Rentals-In-Montemassi.d6361379.Car-Rental-Guide)

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# Montemassi Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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#### Your Montemassi Vacation

When you organize a vacation package to Montemassi, you can relax and enjoy your break knowing that all your travel plans are in order. Uncover the many charms of this lively city while based in a neighborhood like Valpiana, which is good for views. Make your trip to Montemassi even more enjoyable by going sightseeing. [Podere Ristella Vineyards and Winery](https://www.expedia.ca/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Vacation-Attraction), [Church of San Nicola](https://www.expedia.ca/Church-Of-San-Nicola-Roccastrada.d553248621532497684.Vacation-Attraction) and [Sassoforte Castle](https://www.expedia.ca/Sassoforte-Castle-Roccastrada.d685924565073498112.Vacation-Attraction) are among the major attractions worth exploring. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Montemassi vacation is a cinch with Expedia.

## Top Montemassi Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/10f2f159_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Florence Boutique

Historic Centre of Florence

CA $2,126

per person

Apr 30 - May 6

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Florence (FLR)

8.6/10 Excellent! (476 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/50470bbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Grand Hotel Cavour

Historic Centre of Florence

CA $2,864

per person

Apr 30 - May 6

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Florence (FLR)

9.2/10 Wonderful! (1,002 reviews)

Everyone is so nice and helpful! It was also in a great location with an amazing rooftop picturing the entire city.

Reviewed on Feb 20, 2026

![Hotel La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/9b3b942d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

CA $2,624

per person

Apr 30 - May 6

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Florence (FLR)

8.8/10 Excellent! (939 reviews)

Great staff. Helpful. Clean

Reviewed on Feb 13, 2026

![Hotel L'Orologio Firenze](https://images.trvl-media.com/lodging/3000000/2980000/2970900/2970892/3d1f7361_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel L'Orologio Firenze

Historic Centre of Florence

CA $3,344

per person

May 15 - May 20

found 19 hours ago

Roundtrip flight included

Toronto (YTO) to Florence (FLR)

9.6/10 Exceptional! (1,001 reviews)

This hotel is a fantastic value. Very reasonable prices, and Greta location. Amazing, new, clean rooms with fantastic showers and plenty of hot, high-pressure water.

Reviewed on Feb 18, 2026

![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/a67d0954_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Il Rivalta - Place of Charme

Historic Centre of Florence

CA $2,551

per person

May 15 - May 20

found 19 hours ago

Roundtrip flight included

Toronto (YTO) to Florence (FLR)

9.2/10 Wonderful! (420 reviews)

Our room was lovely, clean and well appointed. The staff were very friendly and very helpful!, breakfast was amazing, they cater for everyone. The restaurant staff really friendly and accommodating, we had a birthday meal there which they made extra special too, and overall our stay was made better ( if that’s possible) due to the above. Grazie Mille.

Reviewed on Jan 29, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6361379)

## Ready to book your vacation to Montemassi?

Choose your dates

## Montemassi Hotel Deals

![Borgo Santo Pietro](https://images.trvl-media.com/lodging/5000000/4650000/4644800/4644735/32bc8809_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Borgo Santo Pietro

Loc. Palazzetto Chiusdino SI

[Get rates](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=4644735&PinnedHotelID=4644735&HadPinnedHotel=true&regionId=6361379)

[](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=4644735&PinnedHotelID=4644735&HadPinnedHotel=true&regionId=6361379)

![Grand Hotel Bastiani](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277581/e5c725af_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Grand Hotel Bastiani

Piazza Gioberti 64 Grosseto GR

Fully refundableReserve now, pay when you stay

CA $125

CA $137 total

Mar 6 - Mar 7

includes taxes & fees

8.6/10 Excellent! (227 reviews)

The room was spotless, the bed was comfortable and really liked the old school fittings in the bathroom. During our stay the staff were happy, friendly and very helpful.

Reviewed on Feb 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F03%2F2026&endDate=07%2F03%2F2026&selected=1277581&PinnedHotelID=1277581&HadPinnedHotel=true&regionId=6361379)

![Hotel Airone](https://images.trvl-media.com/lodging/23000000/22490000/22481500/22481472/c64e3088_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hotel Airone

Via Senese, 35 Grosseto GR

Fully refundableReserve now, pay when you stay

CA $167

CA $184 total

Feb 28 - Mar 1

includes taxes & fees

8.4/10 Very Good! (110 reviews)

Clean rooms, friendly staff

Reviewed on Oct 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=22481472&PinnedHotelID=22481472&HadPinnedHotel=true&regionId=6361379)

[See all 2,073 properties in Montemassi](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&regionId=6361379)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### What to do in Montemassi

![La Maliosa Farm Experience & Wine Tasting](https://mediaim.expedia.com/localexpert/44638298/2d7ee171-839d-48ec-b768-c660cead2473.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### La Maliosa Farm Experience & Wine Tasting

CA $73

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/la-maliosa-farm-experience-wine-tasting.a44638298.activity-details)

![From Fiumicino Airport: 1-Way Bus Transfer to Paganico](https://mediaim.expedia.com/localexpert/48206464/247937e6-d734-4208-917c-ad2494f7279f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### From Fiumicino Airport: 1-Way Bus Transfer to Paganico

CA $14

per adult

[](https://expedia.ca/things-to-do/from-fiumicino-airport-1-way-bus-transfer-to-paganico.a48206464.activity-details)

![Welcome to Casale del Bosco](https://mediaim.expedia.com/localexpert/49075566/38f4ac08-b80d-4ccf-bb46-3f53fdc0db59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Welcome to Casale del Bosco

CA $56

per adult

[](https://expedia.ca/things-to-do/welcome-to-casale-del-bosco.a49075566.activity-details)

[See all activities in Montemassi](https://expedia.ca/things-to-do/search?rid=6361379)

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