Top Hotels with Swimming Pools in Montemassi

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Our top choices for Montemassi hotels with a pool

A swimming pool with a view of a valley and mountains.

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

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

A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.

1. Valdonica Winery & Vineyard Residence

Roccastrada

Swim in Tuscan splendour at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.

S$199

includes taxes & fees

5 Nov - 6 Nov

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 Mediterranean-style villa with a gravel driveway, a covered patio, and lush greenery surrounding the property.

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.

2. Tenuta il Sassone - Wine & Food

Gavorrano

Vineyard retreat with seasonal outdoor pool and children's splash area makes family-friendly Tuscan escapes come alive.

S$173

includes taxes & fees

6 Oct - 7 Oct

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

A cozy living room with a fireplace, bookshelves, and a dining area.

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.

3. La Melosa Resort & Spa - Adults Only

Roccastrada

Poolside paradise creates an oasis of serenity at this resort with mountain views.

S$117

includes taxes & fees

7 Oct - 8 Oct

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

A room with a wooden bed, a bathroom with a shower, and a purple wall.

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.

4. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Wine country retreat with a seasonal outdoor pool and on-site vineyard makes for a splendid Tuscan escape.

S$233

includes taxes & fees

11 Oct - 12 Oct

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

A bathroom with a glass shower enclosure, a white toilet, a vanity with a sink, and a window with a view of greenery outside.

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.

5. NonnaNara

Grosseto

S$156

includes taxes & fees

23 Oct - 24 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 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.

6. Montebelli Agriturismo & Country Hotel

Gavorrano

Tranquil wellness retreat with indoor and outdoor pools plus hot tub for year-round aquatic indulgence.

S$102

includes taxes & fees

1 Nov - 2 Nov

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

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

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

7. Conti di San Bonifacio Wine Resort

Gavorrano

Dive into Tuscan bliss at this wine resort's outdoor pool, complete with a poolside bar and sun loungers for ultimate relaxation.

S$858

includes taxes & fees

15 Oct - 16 Oct

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.

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

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

8. VIN Hotel - La Meridiana

Montieri

Splash into Tuscan charm at this farm stay with a seasonal pool and adventure-packed activities.

S$185

includes taxes & fees

19 Oct - 20 Oct

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Choose what matters most at hotels with a pool in Montemassi

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Montemassi Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

8/10 Good

"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"

Castello Banfi - Il Borgo - Relais et Chateaux

10/10 Excellent

"Beautiful property, spacious room, so well maintained. Pool was lovely but a little too quiet, some music would have been a nice touch. A little awkward to get drink/snack at pool and carry it outside while juggling entrance key. White wine appeared to complimentary pool side, why not red? Would love to have experienced e-bikes but unfortunately rained during our available time slot. Enjoyed lunch at the on-site casual restaurant, food and wine parings were excellent, never left us with an empty wine glass. Enjoyed the onsite museum even though not all the information was in English. Would love to return one day."

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."

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 are some hotels with pools in Montemassi?

The Sense Experience Resort - Preferred Hotels & Resorts: Features a children's pool, a seasonal outdoor pool and a private beach. Grand Hotel Bastiani: Provides 2 restaurants, 2 outdoor swimming pools and a full-service spa. Castiglion del Bosco, A Rosewood Hotel: Features 4 outdoor swimming pools, a children's pool and 4 restaurants. Fattoria La Principina Hotel & Congress: Offers 2 restaurants, a pool and a full-service spa. Borgo Santo Pietro: Offers a seasonal outdoor pool, an indoor pool and a full-service spa.

What is there to see and do in Montemassi?

Make a point to visit attractions such as Lago dell'Accesa and Piscina Il Giunco. Discover sights such as Podere Ristella Vineyards and Winery, Rocca di Frassinello Winery and I Canaloni del Torrente Farma during your stay.

When is the best time to book a hotel with a pool in Montemassi?

You may want to think about accommodation that offers an outdoor pool if you're planning to visit Montemassi in the hottest months of August, July or June, when the average temp is 23°C. Accommodation offering an indoor pool may be what you want if you visit during the coldest months of January, February or December, when the average temp is 9°C.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Montemassi Hotels with Swimming Pools

Our top choices for Montemassi hotels with a pool

1. Valdonica Winery & Vineyard Residence

2. Tenuta il Sassone - Wine & Food

3. La Melosa Resort & Spa - Adults Only

4. Valdonica Winery - Chill in Nature Lodge

5. NonnaNara

6. Montebelli Agriturismo & Country Hotel

7. Conti di San Bonifacio Wine Resort

8. VIN Hotel - La Meridiana

9. Tenuta Casteani

10. Country House il Ciliegio

Choose what matters most at hotels with a pool in Montemassi

Top Montemassi Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castello Banfi - Il Borgo - Relais et Chateaux

Montebelli Agriturismo & Country Hotel

Fattoria La Principina Hotel & Congress

Mercure Petriolo Siena Terme Spa Hotel

Antico Casale L'Impostino

Frequently asked questions

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