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

1. Valdonica Winery & Vineyard Residence

Roccastrada

$147

$165 total

includes taxes & fees

Nov 8 - Nov 9

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

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

2. Tenuta il Sassone - Wine & Food

Gavorrano

$102

$120 total

includes taxes & fees

Oct 28 - Oct 29

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

3. La Melosa Resort & Spa - Adults Only

Roccastrada

$85

$97 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

4. Agriturismo Giù al Pozzo

Gavorrano

$75

$92 total

includes taxes & fees

Oct 25 - Oct 26

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 reception desk, potted plants, and a tray with toiletries.

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

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

5. Conti di San Bonifacio Wine Resort

Gavorrano

$546

$600 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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 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.

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

7. Le Vie del Mare Camere

Ribolla

$123

$135 total

includes taxes & fees

Oct 21 - Oct 22

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

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

8. Valdonica Winery - Chill in Nature Lodge

Roccastrada

$177

$197 total

includes taxes & fees

Nov 8 - Nov 9

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

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

9. Tenuta Casteani

Gavorrano

$101

$115 total

includes taxes & fees

Oct 22 - Oct 23

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.

10. Country House il Ciliegio

Roccastrada

$85

$96 total

includes taxes & fees

Oct 23 - Oct 24

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 gazebo with a stone wall and a lamp post in a park setting.

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

11. Historic Farmhouse Casa del Chiodo

Roccastrada

$121

$135 total

includes taxes & fees

Oct 21 - Oct 22

A swimming pool with a view of a hilltop castle.

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

A wine cellar with wooden barrels, a wine rack, and a table set for dining.

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

12. Agriturismo Podere Ristella - Wine&Food

Roccastrada

$90

$124 total

includes taxes & fees

Oct 24 - Oct 25

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

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

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

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

13. Hotel Girifalco - Nature & Relax

Massa Marittima

$58

$75 total

includes taxes & fees

Oct 21 - Oct 22

A swimming pool with a wind turbine, lounge chairs, and a view of the hills.

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

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

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

14. VIN Hotel - La Meridiana

Montieri

$131

$144 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

A pathway leading to a building with a stone-tiled entrance and a wooden door.

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 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.

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

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.

An aerial view of a property with a swimming pool, manicured lawns, and a variety of trees.

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

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.

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 historic building with a stone facade, surrounded by a well-maintained garden with yellow flowers and tall trees.

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

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

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.

An outdoor patio with wooden tables and chairs, stone walls, and potted plants.

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 large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

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

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

A covered outdoor dining area with tables set for a meal, surrounded by glass walls and wooden beams.

20. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

$152

$167 total

includes taxes & fees

Nov 2 - Nov 3

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

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

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Exceptional

Paul

Hotel Girifalco - Nature & Relax

Massa Marittima

10/10 Exceptional

Juan

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Exceptional

Ian

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 long banquet table with chairs, a chandelier, and draped fabric on a stone wall.

Casale San Galgano

Chiusdino

10/10 Exceptional

Jose Manuel

Tenuta Casteani

Gavorrano

10/10 Exceptional

Hermes Affonso

VIN Hotel - La Meridiana

Montieri

10/10 Exceptional

John

Montebelli Agriturismo & Country Hotel

Gavorrano

10/10 Exceptional

G&J

Antico Casale L'Impostino

Civitella Paganico

10/10 Exceptional

Mason

A cozy, open-plan restaurant with a wooden interior and a thatched roof.

A rustic outdoor area with a wooden structure, a stone wall, and a grassy lawn.

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

Agriturismo Sweet Cottage

Grosseto

10/10 Exceptional

This place is AMAZING! I cannot stress what a wonderful (ENGLISH SPEAKING) staff they have! I wish I had planned 2 nights here instead of just one. Wife and I on 9 city tour from north to south (Naples, Anzio, Grosseto, Genoa, Pisa, Milan, Florence, Montepulciano, Rome). Some were 2 night stays (never been there) and others were 1 night only (been there at some time in past). DON’T FORGET TO RESERVE lunch and/or dinner on property. Breakfast was included, but you pay for lunch/supper and...

Michael

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.