Default HTG hotel image

Hotels with Swimming Pool in Montemassi, Roccastrada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Montemassi Hotels with Swimming Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
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 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 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 Mediterranean-style villa with a gravel driveway, a covered patio, and lush greenery surrounding the property.

1. 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.
P7,228
P8,444 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta il Sassone - Wine & Food
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.
An outdoor dining area with tables set for a meal, surrounded by greenery and a wooden pergola.
A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.

2. 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.
P8,643
P9,718 total
includes taxes & fees
Nov 5 - Nov 6
Valdonica Winery & Vineyard Residence
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 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

La Melosa Resort & Spa - Adults Only
Roccastrada
  • Poolside paradise creates an oasis of serenity at this resort with mountain views.
P5,337
P6,082 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 wooden interior with a table set for a meal, featuring a tray with plates, glasses, and a bottle.

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.
P37,932
P42,007 total
includes taxes & fees
Oct 15 - Oct 16
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 covered patio with a table and chairs, a small garden, and a building in the background.
A narrow corridor with a wooden ceiling and a tiled floor, leading to a door at the end.

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.
P4,527
P4,979 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 window with a view of buildings and a plant on the windowsill.
A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

6. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
  • Tuscan paradise awaits with private poolside bar service and children's splash area.
P5,541
P6,236 total
includes taxes & fees
Nov 4 - Nov 5
Country House il Ciliegio
A swimming pool with a curved edge, surrounded by lush greenery and a clear sky.
A covered courtyard with stone columns, a brick floor, and a grassy area.
A dining table with plates of food, a vase with flowers, and a view of a green landscape through large windows.
An outdoor patio with tables and chairs, surrounded by greenery and a stone building.

7. Hotel Girifalco - Nature & Relax

Hotel Girifalco - Nature & Relax
Massa Marittima
  • Dive into a refreshing poolside escape where seasonal swimming meets gorgeous garden views at this bed & breakfast.
P3,266
P4,297 total
includes taxes & fees
Oct 19 - Oct 20
Hotel Girifalco - Nature & Relax
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 room with a wooden bed, a bathroom with a shower, and a purple wall.
A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

8. 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.
P11,328
P12,602 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 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.
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

Tenuta Casteani
Gavorrano
P6,970
P7,948 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta Casteani
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.
A cozy living room with a fireplace, elegant furniture, and a chandelier.
A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.
A bathroom with a bathtub, a chandelier, and a view of the outdoors.

10. Borgo Santo Pietro

Borgo Santo Pietro
Chiusdino
  • Tuscan oasis boasts poolside luxury with cabanas, spa treatments, and hot tub escapes.
P70,402
P78,146 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Santo Pietro
View all properties

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

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 13 hours 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

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.

Explore a world of travel with Expedia