TOP Pet-Friendly Hotels in Montemassi for 2026

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Our top choices for Montemassi pet-friendly hotels

A historic stone building with multiple windows and a courtyard.

A breakfast buffet with various food items and beverages, set in a room with stone walls and a large window.

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

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

1. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Alice

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

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

Rp2.828.941

Rp3.172.689 total

includes taxes & fees

5 Oct - 6 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 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.

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

3. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

Rp10.983.207

Rp12.163.066 total

includes taxes & fees

15 Oct - 16 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 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.

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

4. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

Rp2.053.764

Rp2.401.833 total

includes taxes & fees

6 Oct - 7 Oct

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

5. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

Rp1.758.169

Rp2.056.293 total

includes taxes & fees

1 Oct - 2 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 garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

6. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Rp3.356.088

Rp3.732.265 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A hotel room with a bed, towels, a painting, and a vase with flowers.

7. 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

Rp2.323.460

Rp2.555.806 total

includes taxes & fees

23 Oct - 24 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 bedroom with a bed, a nightstand, a wall-mounted lamp, a window with a view, and a ceiling light fixture.

8. Le Vie del Mare Camere

Ribolla

Rp2.218.122

Rp2.439.934 total

includes taxes & fees

7 Oct - 8 Oct

View all properties

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."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

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"

Hotel Nuova Grosseto

8/10 Good

"Perfectly good place to stay for a quick stopover in Grosseto. Steps from the train station, which was great after a hot journey. Walkable to the cute town square and many restaurants, and a good gelato place 5 minutes away."

Antico Casale L'Impostino

10/10 Excellent

"Monia and Fabio are absolutely delightful hosts! My wife and I were shocked by how kind and accomodating they were - especially with our dietary needs. The food was magnificent, and the vineyard was beautiful! All the staff were attentive and helpful. We would definitely recommend Tenuta L’Impostino to everyone!"

Frequently asked questions

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 option for you and your pet.

What's the best time of year to travel to Montemassi with my pet?

When you travel with your pet, keeping track of the weather can help you make the trip more safe and fun for everyone. 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.

What is there to see and do with your pet in Montemassi?

During your visit, enjoy visiting Podere Ristella Vineyards and Winery and Piscina Il Giunco. When you're in the area, make time for a stop at Lago dell'Accesa.

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Change your mind

Treat yourself

Be picky

Check availability on Montemassi Pet-Friendly Hotels

Our top choices for Montemassi pet-friendly hotels

1. Agriturismo Tenuta di Montemassi La Fattoria

2. Valdonica Winery & Vineyard Residence

3. Conti di San Bonifacio Wine Resort

4. Tenuta il Sassone - Wine & Food

5. Montebelli Agriturismo & Country Hotel

6. Valdonica Winery - Chill in Nature Lodge

7. NonnaNara

8. Le Vie del Mare Camere

9. Country House il Ciliegio

10. Tenuta Casteani

Top Montemassi Hotel Reviews

Grand Hotel Bastiani

Hotel La Pineta

Castiglion del Bosco, A Rosewood Hotel

Montebelli Agriturismo & Country Hotel

Fattoria La Principina Hotel & Congress

Hotel Nuova Grosseto

Antico Casale L'Impostino

Frequently asked questions

Explore a world of travel with Expedia

Search Pet-Friendly Hotels in Montemassi

Change your mind

Treat yourself

Be picky

Check availability on Montemassi Pet-Friendly Hotels

Our top choices for Montemassi pet-friendly hotels

1. Agriturismo Tenuta di Montemassi La Fattoria

2. Valdonica Winery & Vineyard Residence

3. Conti di San Bonifacio Wine Resort

4. Tenuta il Sassone - Wine & Food

5. Montebelli Agriturismo & Country Hotel

6. Valdonica Winery - Chill in Nature Lodge

7. NonnaNara

8. Le Vie del Mare Camere

9. Country House il Ciliegio

10. Tenuta Casteani

Top Montemassi Hotel Reviews

Grand Hotel Bastiani

Hotel La Pineta

Castiglion del Bosco, A Rosewood Hotel

Montebelli Agriturismo & Country Hotel

Fattoria La Principina Hotel & Congress

Hotel Nuova Grosseto

Antico Casale L'Impostino

Frequently asked questions

Explore a world of travel with Expedia