Montemassi Holidays from £288

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Your Montemassi Holiday

When you organise a holiday 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 neighbourhood like Valpiana, which is good for views. Make your trip to Montemassi even more enjoyable by going sightseeing. Podere Ristella Vineyards and Winery, Church of San Nicola and Sassoforte Castle are among the major attractions worth exploring. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Montemassi holiday is a cinch with Expedia.

Top Montemassi Flight + Hotel Deals

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

Hotel Franchi

3 out of 5
Save 100% on your flight
Price was £460, price is now £288 per person
£288
per person
22 Jun - 26 Jun
found 23 hours ago
Return flight included
London (LTN) to Florence (FLR)
7.8/10 Good! (706 reviews)
Improve sound isolation as i could hear everything and it was hard to sleep. but very clean and staff very nice.

Reviewed on 14 May 2026

SPLENDIDE RIVIERA

SPLENDIDE RIVIERA

4 out of 5
Save 100% on your flight
Price was £1,373, price is now £813 per person
£813
per person
7 Aug - 14 Aug
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
9.8/10 Exceptional! (14 reviews)
Simply perfecto ! Superb location. Sea fron balcony room, magical. Full enjoyed our stay.

Reviewed on 1 May 2026

The Poet Hotel

The Poet Hotel

4 out of 5
La Spezia Historic Centre
Save 100% on your flight
Price was £965, price is now £577 per person
£577
per person
7 Aug - 14 Aug
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
9.2/10 Wonderful! (967 reviews)
Hotel is close to the Main Street of the town . Clean room and very good breakfast.

Reviewed on 19 May 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,519, price is now £918 per person
£918
per person
2 Jul - 5 Jul
found 6 hours ago
Return flight included
London (LHR) to Florence (FLR)
9.8/10 Exceptional! (61 reviews)
The ancient building was retrofitted with all the modern elements without compromising its architectural features. The staff was friendly, helpful in suggesting restaurants and making sure we had everything we needed. As a bonus each morning there would be a box delivered to our door with sweet pastries and savory sandwiches from a local bakery! Fabulous start to our day combined with the complimentary coffee and teas already available.

Reviewed on 21 May 2026

LHP Hotel Santa Margherita Palace & SPA

LHP Hotel Santa Margherita Palace & SPA

5 out of 5
Save 100% on your flight
Price was £1,124, price is now £699 per person
£699
per person
7 Aug - 14 Aug
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
8.6/10 Excellent! (409 reviews)
Great location between train station and downtown and ferry docks to Portofino, Fruttoso, etc. We based here to explore Cinque Terre, Portofino and Santa Margherita Hotel features an excellent gym, helpful and engaged staff, clean rooms, solid WiFi and seems dog friendly. The property is well maintained and looks much younger and hipper than the 20 years it’s been around. I’d definitely would stay at LHP again. Did not try food or drinks, but breakfast was 30 euros per person.

Reviewed on 5 May 2026

Montemassi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
180
Max Temp Winter
13ºC
Max Temp Summer
27ºC
Top Sights
Podere Ristella Vineyards and Winery, Castello del Belagaio and Sassoforte Castle

Top hotels in Montemassi

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
The price is £1,815 per night from 7 Jun to 8 Jun
£1,815
7 Jun - 8 Jun
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67 Follonica GR
The price is £63 per night from 28 May to 29 May
£63
28 May - 29 May
includes taxes & fees
9/10 Wonderful! (302 reviews)
"Excellent hotel .breakfast was fantastic Very nice staff and helpful. Right in front of the ocean :across the street. Restos close by 👍"

Reviewed on 24 Apr 2026

Hotel La Pineta
Grand Hotel Bastiani

Grand Hotel Bastiani

4 out of 5
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
The price is £71 per night from 4 Jun to 5 Jun
£71
4 Jun - 5 Jun
includes taxes & fees
Grand Hotel Bastiani
See all 2,137 properties in Montemassi
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside.

Podere Ristella Vineyards and Winery

What to do in Montemassi

La Maliosa Farm Experience & Wine Tasting

La Maliosa Farm Experience & Wine Tasting

£39
per adult
100% of travellers recommend
La Maliosa Farm Experience & Wine Tasting
Welcome to Casale del Bosco

Welcome to Casale del Bosco

£30
per adult
Welcome to Casale del Bosco
See all activities in Montemassi

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.