Default HTG hotel image

Search Hotels with Pool in Montemassi

  • 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 Pool

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Montemassi hotels with a pool

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

Valdonica Winery & Vineyard Residence
Roccastrada
  • Swim in Tuscan splendour at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.
฿4,941
฿5,547 total
includes taxes & fees
8 Nov - 9 Nov
Valdonica Winery & Vineyard Residence
A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
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.
A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

2. 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.
฿2,845
฿3,242 total
includes taxes & fees
15 Oct - 16 Oct
La Melosa Resort & Spa - Adults Only
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 balcony with a view of mountains, featuring a table with chairs, a bottle of wine, and a cactus decoration.
A Mediterranean-style villa with a gravel driveway, a covered patio, and lush greenery surrounding the property.

3. 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.
฿3,868
฿4,518 total
includes taxes & fees
26 Oct - 27 Oct
Tenuta il Sassone - Wine & Food
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 reception desk, potted plants, and a tray with toiletries.

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.
฿18,268
฿20,094 total
includes taxes & fees
8 Nov - 9 Nov
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 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 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.
฿2,723
฿2,996 total
includes taxes & fees
1 Nov - 2 Nov
Montebelli Agriturismo & Country Hotel
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.
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.
฿2,997
฿3,372 total
includes taxes & fees
16 Oct - 17 Oct
Country House il Ciliegio
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.

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.
฿5,946
฿6,616 total
includes taxes & fees
8 Nov - 9 Nov
Valdonica Winery - Chill in Nature Lodge
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.
A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.
A rustic dining area with brick walls, hanging plants, and candle-lit tables.
A cozy living room with a fireplace, elegant furniture, and a chandelier.

8. Borgo Santo Pietro

Borgo Santo Pietro
Chiusdino
  • Tuscan oasis boasts poolside luxury with cabanas, spa treatments, and hot tub escapes.
฿37,523
฿41,651 total
includes taxes & fees
16 Oct - 17 Oct
Borgo Santo Pietro
A swimming pool with a curved edge, surrounded by lush greenery and a clear sky.
An outdoor patio with tables and chairs, surrounded by greenery and a stone building.
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.

9. 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.
฿1,658
฿2,199 total
includes taxes & fees
27 Oct - 28 Oct
Hotel Girifalco - Nature & Relax
A pool area with lounge chairs and umbrellas, surrounded by buildings and trees.
A golf course with a pond, trees, and hills in the background.
An outdoor dining area with tables set for two, surrounded by palm trees and flowering plants.
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.
฿5,126
฿5,638 total
includes taxes & fees
1 Nov - 2 Nov
Il Pelagone Hotel & Golf Resort Toscana
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

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 9 days ago
Riva del Sole Resort & SPA
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 1 month 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 2 months 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 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.

Explore a world of travel with Expedia