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Check availability on Montemassi Hotels with a Pool

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Montemassi hotels with a pool

A swimming pool with a view of a valley and mountains.
A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.
An outdoor dining area with tables set for a meal, surrounded by greenery and a wooden pergola.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

1. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
  • Swim in Tuscan splendor at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.
₩184,796
₩207,792 total
includes taxes & fees
Nov 5 - Nov 6
Valdonica Winery & Vineyard Residence
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 Mediterranean-style villa with a gravel driveway, a covered patio, and lush greenery surrounding the property.
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.

2. Tenuta il Sassone - Wine & Food

Tenuta il Sassone - Wine & Food
Gavorrano
  • Vineyard retreat with seasonal outdoor pool and children's splash area makes family-friendly Tuscan escapes come alive.
₩156,289
₩182,454 total
includes taxes & fees
Oct 26 - Oct 27
Tenuta il Sassone - Wine & Food
A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.
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.

3. La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
  • Poolside paradise creates an oasis of serenity at this resort with mountain views.
₩114,115
₩130,043 total
includes taxes & fees
Oct 25 - Oct 26
La Melosa Resort & Spa - Adults Only
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 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.

4. Conti di San Bonifacio Wine Resort

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.
₩811,042
₩898,167 total
includes taxes & fees
Oct 28 - Oct 29
Conti di San Bonifacio Wine Resort
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 covered patio with a table and chairs, a small garden, and a building in the background.

5. Montebelli Agriturismo & Country Hotel

Montebelli Agriturismo & Country Hotel
Gavorrano
  • Tranquil wellness retreat with indoor and outdoor pools plus hot tub for year-round aquatic indulgence.
₩96,993
₩106,692 total
includes taxes & fees
Nov 1 - Nov 2
Montebelli Agriturismo & Country Hotel
A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.
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.
A window with a view of buildings and a plant on the windowsill.

6. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
  • Tuscan paradise awaits with private poolside bar service and children's splash area.
₩118,466
₩133,324 total
includes taxes & fees
Nov 5 - Nov 6
Country House il Ciliegio
A group of people dining at a table with a view of a valley and 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.
A room with a wooden bed, a bathroom with a shower, and a purple wall.

7. Valdonica Winery - Chill in Nature Lodge

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.
₩242,214
₩269,446 total
includes taxes & fees
Nov 2 - Nov 3
Valdonica Winery - Chill in Nature Lodge
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 interior with exposed wooden beams, a stone fireplace, a cozy seating area, and a large window with curtains.
A rustic room with a stone wall, a glass table with books, and a view of an outdoor patio with chairs and umbrellas.

8. Tenuta Casteani

Tenuta Casteani
Gavorrano
₩149,346
₩170,314 total
includes taxes & fees
Oct 7 - Oct 8
Tenuta Casteani
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.
A bathroom with a bathtub, a chandelier, and a view of the outdoors.
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.

9. Borgo Santo Pietro

Borgo Santo Pietro
Chiusdino
  • Tuscan oasis boasts poolside luxury with cabanas, spa treatments, and hot tub escapes.
₩1,505,274
₩1,670,854 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Santo Pietro
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 beach with blue umbrellas and a wooden deck.
A covered outdoor dining area with tables set for a meal, surrounded by glass walls and wooden beams.

10. Il Pelagone Hotel & Golf Resort Toscana

Il Pelagone Hotel & Golf Resort Toscana
Gavorrano
  • Splash into tuscan bliss at this resort's dreamy pool scene with a children's pool and poolside bar.
₩205,264
₩225,791 total
includes taxes & fees
Nov 1 - Nov 2
Il Pelagone Hotel & Golf Resort Toscana
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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

Riva del Sole Resort & SPA

Riva del Sole Resort & SPA

10/10 Excellent
"Helpful staff. Very clean rooms. Great location. Beach was lovely. Would stay again."
Jennifer 3-night trip
Posted 18 hours ago
Riva del Sole Resort & SPA
Castiglion del Bosco, A Rosewood Hotel

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!"
Ellen 5-night trip
Posted 1 day ago
Castiglion del Bosco, A Rosewood Hotel
Castello Banfi - Il Borgo - Relais et Chateaux

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."
Anna 1-night trip
Posted 3 weeks ago
Castello Banfi - Il Borgo - Relais et Chateaux
Montebelli Agriturismo & Country Hotel

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."
Kathryn 3-night trip
Posted 1 month ago
Montebelli Agriturismo & Country Hotel
Fattoria La Principina Hotel & Congress

Fattoria La Principina Hotel & Congress

8/10 Good
"great facility but needs a general upgrade and remodeling"
Giuseppe 1-night trip
Posted 2 months ago
Fattoria La Principina Hotel & Congress
Mercure Petriolo Siena Terme Spa Hotel

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."
patricia 3-night trip
Posted 3 months ago
Mercure Petriolo Siena Terme Spa Hotel
Antico Casale L'Impostino

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!"
Mason 3-night trip
Posted 4 months ago
Antico Casale L'Impostino

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 pools, and a full-service spa. Castiglion del Bosco, A Rosewood Hotel: Features 4 outdoor 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 like 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 an accommodation with an outdoor swimming pool if you plan to visit Montemassi in the warmest months of August, July, or June when the average temp is 74°F. Lodging offering an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 48°F.

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