Best Montemassi Hotels in 2026 from HK$545 - Fully Refundable Options

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Montemassi

Pet friendly

Apartment

Pool

Villa

Spa

Condo

Hot tub

Family friendly

Waterpark

Farm

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Montemassi hotels

A historic stone building with multiple windows and a courtyard.

An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.

A bedroom with a large bed, wooden beams, a TV, and framed pictures on the wall.

1. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Alice

HK$925

HK$1,035 total

includes taxes & fees

30 Sept - 1 Oct

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

A room with a large window overlooking a vineyard and mountains. There is a stone wall and a wooden shelf with wine bottles and glasses.

A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

A balcony with two wooden chairs overlooking a vineyard and distant mountains.

2. Valdonica Winery & Vineyard Residence

Roccastrada

"After debating between many Tuscan vineyards/B&Bs to stay at, I am so glad we picked this one. The venue was beautiful, the room was nice and clean (with AC), and they had a gorgeous remote pool overlooking the vineyard. The people working were all incredibly kind and accommodating and went above and beyond to make our stay memorable, in addition to the owner. We enjoyed a wine tour/tasting and a cooking class, and had dinner at their restaurant that was one of our best meals in Italy. Our only...

Audrey

HK$1,246

HK$1,398 total

includes taxes & fees

30 Sept - 1 Oct

A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

A wooden interior with a table set for a meal, featuring a tray with plates, glasses, and a bottle.

A bedroom with a large bed, a view of the countryside, and a stone wall.

A cozy living room with a fireplace, wooden beams, stone walls, and a leather sofa.

3. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

HK$4,814

HK$5,331 total

includes taxes & fees

15 Oct - 16 Oct

A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.

A rustic dining area with brick walls, hanging plants, and candle-lit tables.

A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.

A cozy living room with a fireplace, elegant furniture, and a chandelier.

4. Borgo Santo Pietro

Chiusdino

Rachel

HK$8,935

HK$9,918 total

includes taxes & fees

29 Oct - 30 Oct

A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

A fruit basket with apples, pears, bananas, and cherries.

A modern bedroom with a bed, bedside tables, a ceiling light, a window, and a wall-mounted artwork.

A modern bathroom with a glass shower enclosure, a sink, a toilet, and a window providing natural light.

5. Le Vie del Mare Camere

Ribolla

HK$977

HK$1,075 total

includes taxes & fees

1 Oct - 2 Oct

A swimming pool with clear blue water, a person standing on the edge, and another person swimming. There are lounge chairs and an umbrella in the background.

A hotel room with a fireplace, a desk with a chair, a bed with a blue and white bedspread, and a view of the outdoors through large windows.

A stone staircase leading up to a structure, surrounded by lush greenery and trees.

A room with a desk, chair, and a large window with curtains.

6. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

HK$900

HK$1,053 total

includes taxes & fees

6 Oct - 7 Oct

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

A window with a view of buildings and a plant on the windowsill.

A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.

A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

7. Country House il Ciliegio

Roccastrada

Maaike

HK$717

HK$807 total

includes taxes & fees

28 Oct - 29 Oct

A group of people dining at a table with a view of a valley and mountains.

A panoramic view of a vineyard with rolling hills, a clear sky, and distant mountains.

A bedroom with a bed, a desk with a bottle and glasses, a red cabinet, and a view of the outdoors.

A long table set for a formal outdoor event, surrounded by a vineyard.

8. Valdonica Winery - Chill in Nature Lodge

Roccastrada

HK$1,478

HK$1,644 total

includes taxes & fees

4 Oct - 5 Oct

A stone house with a swimming pool, red shutters, and a covered patio.

A stone building with a staircase leading to a terrace, flags, and a view of a parking area and hills.

A stone building with a red shuttered window, a colorful mosaic, and a staircase leading to a hilltop view.

A rustic stone building with a courtyard, a wooden cart, and a tree.

9. NonnaNara

Grosseto

"Grosse maison perdue dans la campagne qui a été une superbe découverte. Nous avions un magnifique appartement qui donnait sur une belle piscine magnifiquement entretenue. Le personnel est très avenant avec un remerciement spécial pour Fatima qui nous a accueillis en français est s'est occupé de nous toute la soirée. Elle nous a concocté un excellent repas le soir avec des produits du terroir. Un grand merci pour elle qui était encore présente tôt au petit déjeuner. Excellente expérience à...

Marie

HK$1,023

HK$1,126 total

includes taxes & fees

23 Oct - 24 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.

A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

A large stone house with a swimming pool, surrounded by lush greenery and hills.

A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.

10. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

HK$677

HK$772 total

includes taxes & fees

25 Oct - 26 Oct

A clear pool with visible mineral deposits, a pebble beach, and a mountainous landscape in the background.

An open window with a view of a mountainous landscape and a flower box on the windowsill.

An interior with a brick archway, stone walls, and modern seating.

A rustic interior with exposed brick walls, a stone fireplace, and wooden beams. There are leather sofas, a round table, and potted plants.

11. VIN Hotel - La Meridiana

Montieri

Anastasia

HK$1,140

HK$1,254 total

includes taxes & fees

29 Sept - 30 Sept

A swimming pool with a waterfall feature, large windows, and a lounge chair.

A living room with a grey sofa, a coffee table, and a potted plant with red flowers. There are shelves with various bottles and jars, and a wall-mounted display with three decorative plates.

A covered patio with a table and chairs, a small garden, and a building in the background.

A narrow corridor with a wooden ceiling and a tiled floor, leading to a door at the end.

12. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

HK$771

HK$901 total

includes taxes & fees

1 Oct - 2 Oct

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

A stone building with a wooden door, green shutters, and two potted plants.

A dining table set with wine glasses and a vase with flowers, a fireplace with a fire, and a stone wall.

A view through a window of a mountainous landscape with autumn foliage and a house in the distance.

13. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

HK$797

HK$895 total

includes taxes & fees

5 Oct - 6 Oct

A spacious lounge area with a high ceiling, ornate chandelier, and a variety of seating options including sofas and armchairs.

A large, multi-story building surrounded by lush greenery and fields.

A table with a bottle of wine, glasses, and a variety of food items including bread and cured meats.

An indoor water feature with a brick archway and a view to the outside.

14. L'Andana

Castiglione della Pescaia

Aleksandr

HK$3,375

HK$3,802 total

includes taxes & fees

5 Oct - 6 Oct

A swimming pool with water flowing from a tap, surrounded by lounge chairs and umbrellas.

A stone building with a red door, surrounded by gravel and potted plants.

An outdoor dining setup with a stone building in the background, a table with plates, cutlery, and a bottle of red drink.

A rustic interior with exposed wooden beams, a stone fireplace, a cozy seating area, and a large window with curtains.

15. Tenuta Casteani

Gavorrano

Andrew

HK$965

HK$1,097 total

includes taxes & fees

29 Sept - 30 Sept

An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

A coastal beach with clear turquoise waters, a sandy shoreline, and a forested area with parked cars.

A marina with numerous boats docked, a central building, and a clear view of the sea.

A dining area with a long table set for breakfast, featuring various food items and a clock on the wall.

16. Agriturismo Giù al Pozzo

Gavorrano

Micaiah

HK$671

HK$774 total

includes taxes & fees

4 Oct - 5 Oct

A dining table with plates of food, a vase with flowers, and a view of a green landscape through large windows.

A bedroom with a canopy bed, a desk, and a view of greenery outside.

A covered courtyard with stone columns, a brick floor, and a grassy area.

A swimming pool with a curved edge, surrounded by lush greenery and a clear sky.

17. Hotel Girifalco - Nature & Relax

Massa Marittima

Lucy

HK$415

HK$545 total

includes taxes & fees

11 Oct - 12 Oct

A pool with a modern water feature and a stone structure.

A large, multi-story building with a swimming pool, surrounded by lush greenery.

A buffet table with various desserts and a long dining area with tables and chairs.

A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

18. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

HK$670

HK$737 total

includes taxes & fees

29 Sept - 30 Sept

A beach with blue umbrellas and a wooden deck.

A pool area with lounge chairs and umbrellas, surrounded by buildings and trees.

An outdoor dining area with tables set for two, surrounded by palm trees and flowering plants.

A golf course with a pond, trees, and hills in the background.

19. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

Matthias

HK$1,378

HK$1,569 total

includes taxes & fees

1 Oct - 2 Oct

A stone wall with a view of rolling hills and mountains.

A stone building with a swimming pool, lounge chairs, and umbrellas.

A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.

20. Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

Jason

HK$6,986

HK$7,773 total

includes taxes & fees

28 Oct - 29 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Montemassi Hotel Reviews

Grand Hotel Bastiani

10/10 Excellent

"Great location inside the city walls to explore Grosetto. Lots of great restaurants."

Hotel La Pineta

8/10 Good

"Excellent breakfast and dinner at same restaurant with beautiful patio. Nice lunch cafe in front also for aperitif. Close to street though. Very friendly staff. Rooms are a bit cold with no decor. Rooms close to stairs and elevator are noisy. We had room 112. Heard everything from the hallways which was annoying at night. Room had a very strong disinfectant odor. Overall highly recommend the hotel."

Hotel L'Approdo

10/10 Excellent

"Clean rooms excellent location"

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

L'Andana

10/10 Excellent

"Excellent place"

Hotel Girifalco - Nature & Relax

10/10 Excellent

"Charming hotel. Excellent breakfast. I would recommend it"

Montebelli Agriturismo & Country Hotel

8/10 Good

"If you are driving here you may be surprised by the rough and sometimes narrow track to the hotel - especially if you meet oncoming cars. We liked the dining experience (lunch and dinner were very good and breakfast was ok). The spa was ok too - probably better on a cooler day. We loved the wine and overall had a very pleasant stay here. Very glad to have air con in the room."

Fattoria La Principina Hotel & Congress

8/10 Good

"great facility but needs a general upgrade and remodeling"

Mercure Petriolo Siena Terme Spa Hotel

10/10 Excellent

"Las habitaciones son super lindas y espaciosas. El desayuno es completo y variado. Estuve con mi familia muy a gusto. Fue una estancia placentera. Lo recomiendo."

More cheap stays in Montemassi

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR

Get rates

8.6/10 Excellent! (11 reviews)

Guadalupe Tuscany Resort

Strada Provinciale Del Bozzone Grosseto GR

Get rates

9.8/10 Exceptional! (28 reviews)

Baia Etrusca

Località Torre Mozza, 20 Piombino LI

Get rates

8/10 Very good! (24 reviews)

Bio Tenuta di Paganico - I Roggeti

Via Della Stazione, 10 Civitella Paganico GR

Get rates

8/10 Very good! (1 review)

Hotel C'era Una Volta

Via Balzini 11 Castiglione della Pescaia GR

Get rates

9.6/10 Exceptional! (49 reviews)

Podere Valmarina

Via Aurelia Nord 10 Grosseto GR

Get rates

9.2/10 Wonderful! (5 reviews)

Frequently asked questions

Where is the best place for a stay in Montemassi?

The Sense Experience Resort - Preferred Hotels & Resorts, located 18 mi (28.9 km) from the heart of Montemassi, is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are Grand Hotel Bastiani and Castiglion del Bosco, A Rosewood Hotel. See all available top hotels, or vacation rentals in Montemassi.

What are some of the best holiday rentals that Montemassi has to offer?

Casa Viale Italia - homely house with direct access to the sandy beach: This holiday home rental outside of Montemassi is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Montemassi.

If I need to cancel my hotel reservation in Montemassi, will I receive a refund?

Yes! Most hotel bookings are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Montemassi.

What's the best dog-friendly accommodation option in Montemassi?

Agriturismo Tenuta di Montemassi La Fattoria is a top dog-friendly option for your stay. Tenuta Montemassi Podere Montauzzo is another good option for a stay with your pet. See more pet-friendly hotel accommodations in Montemassi.

What are some accommodation options with pools in Montemassi?

The Sense Experience Resort - Preferred Hotels & Resorts: Offers a children's pool, a seasonal outdoor pool and a private beach. Castiglion del Bosco, A Rosewood Hotel and Fattoria La Principina Hotel & Congress are a couple of other choices that offer an on-site pool. View all hotels with pools in Montemassi.

What is staying in Montemassi like?

Visitors will definitely enjoy all that Montemassi has to offer. In Montemassi, there are 9 hotels and other accommodation options to choose from. Find out more about Montemassi.

What are the top places to visit in Montemassi?

Places to visit in the wider area include Podere Ristella Vineyards and Winery, Piscina Il Giunco and Lago dell'Accesa. You'll also find I Canaloni del Torrente Farma and Cathedral of Massa Marittima in the area. Take a look at what more there is to see and do in Expedia's Montemassi guide.

What's the weather like in Montemassi?

The hottest months are usually August and July, with an average temperature of 23°C, while the coldest months are January and February, with an average of 9°C. Average annual precipitation for Montemassi is 794 mm.

Montemassi hotels from HK$545

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montemassi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Montemassi hotels

1. Agriturismo Tenuta di Montemassi La Fattoria

2. Valdonica Winery & Vineyard Residence

3. Conti di San Bonifacio Wine Resort

4. Borgo Santo Pietro

5. Le Vie del Mare Camere

6. Tenuta il Sassone - Wine & Food

7. Country House il Ciliegio

8. Valdonica Winery - Chill in Nature Lodge

9. NonnaNara

10. La Melosa Resort & Spa - Adults Only

11. VIN Hotel - La Meridiana

12. Montebelli Agriturismo & Country Hotel

13. Historic Farmhouse Casa del Chiodo

14. L'Andana

15. Tenuta Casteani

16. Agriturismo Giù al Pozzo

17. Hotel Girifalco - Nature & Relax

18. Mercure Petriolo Siena Terme Spa Hotel

19. Il Pelagone Hotel & Golf Resort Toscana

20. Castello Banfi - Il Borgo - Relais et Chateaux

Top Montemassi Hotel Reviews

Grand Hotel Bastiani

Hotel La Pineta

Hotel L'Approdo

Castiglion del Bosco, A Rosewood Hotel

L'Andana

Hotel Girifalco - Nature & Relax

Montebelli Agriturismo & Country Hotel

Fattoria La Principina Hotel & Congress

Mercure Petriolo Siena Terme Spa Hotel

More cheap stays in Montemassi

Hotel Massa Vecchia

Guadalupe Tuscany Resort

Baia Etrusca

Bio Tenuta di Paganico - I Roggeti

Hotel C'era Una Volta

Podere Valmarina

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app