Hotels in Montemassi

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Where to stay in Montemassi?

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

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

A swimming pool with a view of a valley and 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.

1. Valdonica Winery & Vineyard Residence

Roccastrada

$148

$166 total

includes taxes & fees

Nov 8 - Nov 9

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

A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.

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.

2. La Melosa Resort & Spa - Adults Only

Roccastrada

$85

$97 total

includes taxes & fees

Oct 25 - Oct 26

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

A balcony with a view of mountains, featuring a table with chairs, a bottle of wine, and a cactus decoration.

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

3. Tenuta il Sassone - Wine & Food

Gavorrano

$102

$120 total

includes taxes & fees

Oct 29 - Oct 30

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 poolside area with a wooden deck, lounge chairs, and a stone building with arched windows.

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.

4. Conti di San Bonifacio Wine Resort

Gavorrano

$546

$600 total

includes taxes & fees

Nov 11 - Nov 12

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 bedroom with a large bed, a wooden headboard, a nightstand, and a window with a view of the outdoors.

5. Agriturismo Giù al Pozzo

Gavorrano

$75

$92 total

includes taxes & fees

Oct 25 - Oct 26

A restaurant with outdoor seating, a bar area, and a view of the landscape.

A narrow hallway with a brick archway, a window, and framed pictures on the walls.

A stone building with a wooden door and a circular window.

A dining table with a scenic view, wine bottles on shelves, and a potted plant.

6. B&B da Nada Locanda Toscana

Roccastrada

$82

$92 total

includes taxes & fees

Nov 3 - Nov 4

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

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

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

A bedroom with a bed, a nightstand, a wall-mounted lamp, a window with a view, and a ceiling light fixture.

7. Le Vie del Mare Camere

Ribolla

$123

$135 total

includes taxes & fees

Oct 30 - Oct 31

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.

A rustic room with a stone wall, a glass table with books, and a view of an outdoor patio with chairs and umbrellas.

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

8. Tenuta Casteani

Gavorrano

$101

$116 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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

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

9. Valdonica Winery - Chill in Nature Lodge

Roccastrada

$177

$197 total

includes taxes & fees

Nov 8 - Nov 9

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

A dining area with wooden beams, stone walls, and a fireplace. Tables are set with wine glasses and cutlery.

10. Historic Farmhouse Casa del Chiodo

Roccastrada

$121

$135 total

includes taxes & fees

Nov 3 - Nov 4

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

A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.

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.

11. Country House il Ciliegio

Roccastrada

$85

$96 total

includes taxes & fees

Oct 23 - Oct 24

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

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 bedroom with a four-poster bed, a balcony with a view, and a bedside table with a lamp.

12. Hotel Girifalco - Nature & Relax

Massa Marittima

$58

$75 total

includes taxes & fees

Oct 22 - Oct 23

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

A table set outdoors with a view of rolling hills and a tall tree 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.

13. VIN Hotel - La Meridiana

Montieri

$131

$144 total

includes taxes & fees

Oct 22 - Oct 23

A swimming pool with a view of a hilltop castle.

A courtyard with a stone column, potted plants, and a view of a hilltop castle.

A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.

An outdoor patio with a pergola, tables, chairs, and a view of rolling hills.

14. Agriturismo Podere Ristella - Wine&Food

Roccastrada

$90

$124 total

includes taxes & fees

Oct 25 - Oct 26

A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

A glass-enclosed structure with a wooden deck, surrounded by various plants and a garden.

A small, modern house with a sliding glass door, surrounded by lush greenery and a well-maintained garden.

A living room with a wooden ceiling, a sofa, a dining table with chairs, a television, and a cabinet.

15. Agriturismo Benvenuti

Roccastrada

$70

$90 total

includes taxes & fees

Oct 23 - Oct 24

An outdoor seating area with a wooden bench, potted plants, and a table with a purple chair.

A swimming pool with a clear blue water, surrounded by white lounge chairs and a wooden deck.

A room with a bed, a chair, a green door, a window with a view of trees, and a painting on the wall.

A kitchen with white cabinets, a checkered backsplash, a dining table with a quilted tablecloth, and a green upholstered chair.

16. Il Belvedere Country Houses

Massa Marittima

$73

$81 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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.

17. Montebelli Agriturismo & Country Hotel

Gavorrano

$81

$89 total

includes taxes & fees

Nov 1 - Nov 2

A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

A spacious living room with a fireplace, multiple seating options, and large windows with curtains.

A covered outdoor seating area with stone pillars, a table, and chairs.

A rustic stone building with a tiled roof, a covered patio with outdoor seating, and well-maintained gardens.

18. Antico Casale L'Impostino

Civitella Paganico

$131

$144 total

includes taxes & fees

Oct 25 - Oct 26

A long table set for a meal outdoors with white tablecloths, woven placemats, and potted plants.

A building with a stone facade and multiple windows.

A large estate with multiple buildings, expansive fields, and a winding road connecting them.

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

19. Agriturismo San Galgano

Chiusdino

$87

$99 total

includes taxes & fees

Oct 26 - Oct 27

A two-story building with a central courtyard, balconies, and a well-maintained garden with pink flowers.

A hammock chair in a lush garden with a wooden structure in the background.

A bedroom with a bed, a nightstand, a dresser, a window, and a shelf with decorative items.

A kitchen with green cabinets, a tiled backsplash, a window with a curtain, and a dining table with chairs.

20. Agriturismo il vecchio imposto

Massa Marittima

$92

$105 total

includes taxes & fees

Oct 25 - Oct 26

View all properties

Go beyond your typical stay in Montemassi

Check out reviews of Montemassi hotels guests love

Tenuta il Sassone - Wine & Food

Gavorrano

10/10 Exceptional

Kathy

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Exceptional

Josh

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Exceptional

Paul

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Exceptional

Ian

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

A bathroom with a bathtub, a chandelier, and a view of the outdoors.

Borgo Santo Pietro

Chiusdino

10/10 Exceptional

My husband and I have been fortunate to stay in many of the best hotels, both large and small, in the world. Borgo Santo Pietro has now seized the "top spot", surpassing our former favorite on the Amalfi coast. No detail has been missed. The rooms are exquisite, the service impeccable, the grounds beautiful and the food is world class. We enjoyed our five course tasting menu so much one evening that we requested the alternative tasting menu the following evening. While incredibly inventive, the...

A.K.Y.

La Melosa Resort & Spa - Adults Only

Roccastrada

10/10 Exceptional

raul

B&B da Nada Locanda Toscana

Roccastrada

10/10 Exceptional

We stayed here for three nights and had an incredible experience. The room was clean, offered a beautiful view, and had reliable Wi-Fi. The location is perfect for exploring, only an hour's drive to Montalcino and incredibly close to several fantastic wineries. The restaurant itself is absolutely fantastic: The panoramic views are amazing, the food is to die for (home cooking style), and the wine selection is excellent. Laura, her husband, and their son, Leonardo, are wonderful, welcoming...

Alexandre

Agriturismo Giù al Pozzo

Gavorrano

10/10 Exceptional

Micaiah

VIN Hotel - La Meridiana

Montieri

10/10 Exceptional

John

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

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

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

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

Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

10/10 Exceptional

Castello Banfi - Il Borgo is either a great place to anchor your restoration or to invigorate your exploration. There's plenty to do on property: a wine tour through the high-tech wine production facility; wine tasting overlooking the Tuscan landscape (you have a substantial selection to choose from); lounging by the pool overlooking the many acres of grape vines, olive and plum trees, and the hills beyond; a visit to their glass museum; an intimate cooking class with one of the top Chefs in...

Greg

Tenuta Casteani

Gavorrano

10/10 Exceptional

Hermes Affonso

An infinity pool with lounge chairs and umbrellas, surrounded by a forested hillside.

An aerial view of a villa with a swimming pool, terraced gardens, and a stone pathway.

A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.

An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Exceptional

Ray

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

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

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

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

L'Andana

Castiglione della Pescaia

10/10 Exceptional

Great property. Great staff. Food was incredible both in quality, taste and the ambiance surrounding dining. One note is that Expedia and their site make it appear that there is one room for each category. We stayed in the prestigious suite and thought we'd have the small pool within the room. We were given another room and while it was stunning, we did suggest updating their site so it would clarify. Nevertheless, a great quiet get away while touring Italy's Tuscan region!

Todd

A covered patio area with stone walls, wooden beams, and outdoor furniture.

A pathway leading to a stone building with multiple windows and a covered area on the left.

A large, historic building complex with multiple structures, surrounded by lush green fields and trees, under a partly cloudy sky.

A room with a blue sofa, a dining table with chairs, a potted plant, and a view through a glass door to the outside.

Casale San Galgano

Chiusdino

10/10 Exceptional

Jose Manuel

Montebelli Agriturismo & Country Hotel

Gavorrano

10/10 Exceptional

G&J

Antico Casale L'Impostino

Civitella Paganico

10/10 Exceptional

Mason

Hotel Girifalco - Nature & Relax

Massa Marittima

10/10 Exceptional

Juan

An aerial view of a historic building complex with a central tower, surrounded by lush greenery and vineyards.

An arched doorway leading to a stone terrace with a vineyard view.

A spacious living area with a high ceiling, large windows, and a kitchen in the background.

A terrace with stone walls, a table, and chairs, overlooking a green landscape with hills and a partly cloudy sky.

Wine Relais in Montecucco

Cinigiano

10/10 Exceptional

Christopher

A modern house with a stone facade, a swimming pool, and outdoor seating.

A wooden room with a bed, a chair, and a view of a mountainous landscape through large windows.

A cozy living room with a large wooden table, comfortable seating, and a view of the countryside.

A covered outdoor dining area with stone flooring and metal chairs, overlooking a lush landscape.

Castello Di Vicarello

Cinigiano

10/10 Exceptional

John

Frequently Asked Questions

What accommodations do travelers recommend in Montemassi?

Guests like Montebelli Agriturismo & Country Hotel and Hotel Girifalco - Nature & Relax.

Where can I find free parking at my hotel in Montemassi?

Agriturismo Tenuta di Montemassi La Fattoria offers the perk of free parking.

Can I book a refundable accommodation in Montemassi?

If you need the flexibility to change your travel plans to Montemassi, most accommodations offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in Montemassi be like during my vacation?

August and July are typically the warmest months in Montemassi when the average temp is 74°F. January and February are the coldest months when the average temperature is 48°F. November and October are the months with the most rain.

Why should I book my Montemassi hotel through Hotels.com?

There are lots of reasons to book your Montemassi trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.