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Find Hotels with a Pool in Montegrossi from CA $110

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Check availability on Montegrossi Hotels with a Pool

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

Our top choices for Montegrossi hotels with a pool

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone building with a tower, surrounded by people dining at tables with candles.
A stone archway leading to a window with a view of tall trees and a distant landscape.
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

1. 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.
CA $217
CA $252 total
includes taxes & fees
Oct 27 - Oct 28
Castello di Tornano Wine Resort
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
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.
A dining table with wine glasses, a bottle, and plates of food, set against a window with a view of a balcony and flowers.

2. 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.
CA $166
CA $193 total
includes taxes & fees
Nov 2 - Nov 3
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 modern bathroom with a freestanding bathtub, a vanity with a mirror, and marble walls.

3. 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.
CA $151
CA $175 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Palazzo San niccolò & Spa
A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

4. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
  • Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.
CA $236
CA $269 total
includes taxes & fees
Nov 3 - Nov 4
Hotel Villa Campomaggio
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.
A villa with a swimming pool, outdoor seating, and a garden.
An outdoor dining area with a pool, potted plants, and umbrellas.

5. 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.
CA $232
CA $304 total
includes taxes & fees
Oct 16 - Oct 17
Relais Vignale & Spa
A pool surrounded by lush greenery and vineyards, with a stone building in the background.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
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.

6. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
  • Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.
CA $95
CA $110 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
An indoor swimming pool with clear glass walls, wooden beams, and large windows.
A courtyard with stone flooring, arched walkways, and a central fountain.
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.

7. 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.
CA $167
CA $187 total
includes taxes & fees
Nov 2 - Nov 3
Villa Casagrande Resort & SPA
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.
CA $118
CA $136 total
includes taxes & fees
Oct 25 - Oct 26
Borgo di Pietrafitta Relais
A swimming pool with a view of a historic building surrounded by olive trees.
An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.
A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.
A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

9. Castello di Meleto

Castello di Meleto
Gaiole in Chianti
  • Seasonal outdoor pool at Tuscan farm stay with vineyard views and sun loungers for serene relaxation amid the countryside.
CA $189
CA $220 total
includes taxes & fees
Oct 8 - Oct 9
Castello di Meleto
A pool with a view of a mountainous landscape and a village in the background.
A stone building with a tiled roof, a stone pathway, and a well-maintained lawn.
A stone building with a tiled roof, surrounded by a well-maintained garden with potted plants and a pathway.
A stone building with a tiled roof, surrounded by a well-maintained garden and a view of rolling hills.

10. Cavarchino B&B

Cavarchino B&B
Gaiole in Chianti
CA $203
CA $236 total
includes taxes & fees
Nov 7 - Nov 8
Cavarchino B&B
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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
"A hidden gem in a central location. The front desk staff were very welcoming and accommodating. Clean, spacious rooms. Great food and drinks at the restaurant. Thank you for an enjoyable stay!"
Casey 4-night trip
Posted 19 hours ago
Hotel Borgo San Luigi
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."
Sonja 3-night trip
Posted 5 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Villa Pitiana

Villa Pitiana

10/10 Excellent
"Beautiful property with priceless views. The on-site restaurant also offered a nice light lunch. The pool area could have been spruced up a bit with some better furniture, but the room was beautiful. Be careful when using the shower as well as it is easy for the water to spray onto the floor. Make sure you understand where the property is located before booking as it is quite a ways outside of Florence city center. I rented a car and drove through the Tuscan hills to arrive."
Connor 1-night trip
Posted 13 days ago
Villa Pitiana
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 1 month ago
Hotel Italia

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 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 like Borgo di Vescine - Tenute di Castelvecchi and Chianti Observatory. During your stay, check out 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 that has an outdoor pool if you will be visiting Montegrossi in the warmest months of August, July, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 44°F.

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