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Check availability on Montegrossi Hotels with Pool

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Montegrossi hotels with a pool

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A narrow street with buildings on either side, a flag, and a bench.
A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.
A couple dining at an outdoor table with a view of the countryside.

1. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
  • Sun-kissed pools in tuscan splendour beckon with historic charm and breathtaking views.
£90
includes taxes & fees
23 Nov - 24 Nov
Palazzo Leopoldo Dimora Storica & Spa
A spa area with a stone ceiling, a pool, and two sun loungers.
A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.
An outdoor cafe with tables and chairs, a yellow umbrella, and a stone building in the background.
A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

2. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
  • Dive into year-round pool perfection with indoor and seasonal outdoor swimming options at this elegant Tuscan retreat.
£86
includes taxes & fees
15 Nov - 16 Nov
Hotel Palazzo San niccolò & Spa
A pool surrounded by lush greenery and vineyards, with a stone building in the background.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

3. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
  • Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.
£61
includes taxes & fees
2 Nov - 3 Nov
Agriturismo San Sano
A pool area with a stone wall, a wooden bridge, and a castle-like structure in the background.
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
A stone building with a tower, surrounded by people dining at tables with candles.
A historic stone building with a large arched window and a small balcony.

4. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
  • Poolside bliss awaits at this Tuscan wine resort where medieval castle meets vineyard views.
£132
includes taxes & fees
26 Oct - 27 Oct
Castello di Tornano Wine Resort
An indoor swimming pool with clear glass walls, wooden beams, and large windows.
A stone-walled room with a brick ceiling, featuring a row of white sofas and a small table with a candle.
A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.
A historic building with a stone facade, arched entrance, and a wooden balcony.

5. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
  • Swim through captivating seasons at this hotel with both indoor and outdoor pools, spa treatments, and an attached winery.
£91
includes taxes & fees
8 Nov - 9 Nov
Villa Casagrande Resort & SPA
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.
A restaurant with a table set for two, overlooking a scenic landscape.
A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

6. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
  • Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.
£168
includes taxes & fees
27 Oct - 28 Oct
Relais Vignale & Spa
A resort with a large swimming pool, sun loungers, and umbrellas.
An outdoor dining area with multiple tables and umbrellas, surrounded by greenery and hills in the background.
A modern bedroom with a large bed, a wooden headboard, a built-in bathtub, and a stone wall.
A dining area with a wooden table, chairs, and a decorative glass centerpiece.

7. Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
  • Discover rustic elegance at this Tuscan farm stay with a seasonal outdoor pool, poolside bar, and sweeping views of green hills.
£39
includes taxes & fees
3 Nov - 4 Nov
Palagina la cascina
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.
A stone building with a courtyard, a covered seating area, and a small bell tower.
A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
A cozy living room with a stone fireplace, striped sofas, and a coffee table.

8. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
£82
includes taxes & fees
1 Nov - 2 Nov
Borgo di Pietrafitta Relais
A rectangular swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.
A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.
A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.
A traditional stone building with a garden featuring geometric hedges and potted plants.

9. Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti
  • Rustic Tuscan farm stay captivates with a seasonal outdoor pool and garden views in the heart of wine country.
£132
includes taxes & fees
1 Nov - 2 Nov
Badia a Coltibuono
A swimming pool with lounge chairs and umbrellas, surrounded by greenery.
An outdoor patio area with tables and chairs, a reception desk, and potted plants.
A view from a covered outdoor area with a paved floor, leading to a garden with various plants and a distant landscape.
A stone building with a rustic exterior, surrounded by lush greenery and outdoor seating areas.

10. Hotel Villa San Giorgio

Hotel Villa San Giorgio
Poggibonsi
£49
includes taxes & fees
25 Nov - 26 Nov
Hotel Villa San Giorgio
View all properties

Choose what matters most at hotels with a pool in Montegrossi

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Montegrossi Hotel Reviews

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."
John 2-night trip
Posted 1 hour ago
Hotel Borgo San Luigi
Hotel Athena

Hotel Athena

10/10 Excellent
"Over all a good hotel in a good location, a little dated but clean and breakfast good"
Suzanne 2-night trip
Posted 5 hours ago
Hotel Athena
Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."
Kurt 1-night trip
Posted 5 days ago
Hotel Italia
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 2 weeks ago
Castello di Spaltenna- Small Luxury Hotels of the World

Frequently asked questions

What are some hotels with pools in Montegrossi?
La Certosa di Pontignano: Offers a children's pool, a seasonal outdoor pool and a rooftop terrace. Hotel Athena: Features a rooftop terrace, an outdoor pool and a snack bar/deli. Hotel Executive: Features an indoor pool, an outdoor pool and 2 restaurants. NH Siena: Provides 2 restaurants, 2 outdoor swimming pools and a full-service spa. Hotel Chiusarelli: Hotel located near Piazza del Campo. Features a children's pool, a seasonal outdoor pool and free self parking.
What is there to see and do in Montegrossi?
Make a point to visit attractions such as Borgo di Vescine - Tenute di Castelvecchi and Chianti Observatory. During your stay, visit sights such as Badia a Coltibuono, Meleto Castle and Cantalici Winery.
When is the best time to book a hotel with a pool in Montegrossi?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Montegrossi in the warmest months of August, July or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 6°C.

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