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Hotels with Swimming Pool in Montegrossi, Gaiole in Chianti

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Check availability on Montegrossi Hotels with Swimming Pool

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

Our top choices for Montegrossi hotels with a pool

An outdoor dining area with a table set for two, overlooking a pool and vineyard.
An outdoor dining area with a pool, potted plants, and umbrellas.
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.

1. 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.
P10,984
P14,269 total
includes taxes & fees
Oct 27 - Oct 28
Relais Vignale & Spa
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A stone building with a garden, tall trees, and a clear blue sky.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
A sunlit patio with a glass roof, stone walls, and outdoor seating.

2. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
  • Serene pools with vineyard views offer both indoor and outdoor aquatic escapes.
P20,984
P23,795 total
includes taxes & fees
Oct 30 - Oct 31
Castello di Spaltenna- Small Luxury Hotels of the World
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A couple dining at an outdoor table with a view of the countryside.
A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.
A dining table with wine glasses, a bottle, and plates of food, set against a window with a view of a balcony and flowers.

3. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
  • Sun-kissed pools in tuscan splendor beckon with historic charm and breathtaking views.
P6,600
P7,687 total
includes taxes & fees
Nov 23 - Nov 24
Palazzo Leopoldo Dimora Storica & Spa
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.
A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.
A room with a view of a forest through a window, a table with a lamp, and a chair.
A building with a stone facade, a central arched doorway, and a window with a decorative frame.

4. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
  • Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.
P17,312
P19,613 total
includes taxes & fees
Nov 16 - Nov 17
Dievole Wine Resort
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 spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

5. 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.
P10,492
P11,969 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Villa Campomaggio
A spa area with a stone ceiling, a pool, and two sun loungers.
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.
A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

6. 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.
P5,886
P6,902 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Palazzo San niccolò & Spa
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.
A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.
A table set for breakfast with various dishes, drinks, and a newspaper.

7. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
  • Dive into tranquil luxury at this hotel's indoor and seasonal outdoor pools, complemented by a poolside bar and loungers.
P41,036
P45,852 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Le Fontanelle
A poolside area with lounge chairs and umbrellas.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.
A modern living room with a white sofa, armchairs, and a coffee table.
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

8. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
P17,098
P19,236 total
includes taxes & fees
Oct 26 - Oct 27
Chapter Chianti, a Member of Design Hotels
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A historic stone building with a large arched window and a small balcony.
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.

9. 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.
P9,669
P11,205 total
includes taxes & fees
Oct 26 - Oct 27
Castello di Tornano Wine Resort
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.
A large building with multiple rooms, surrounded by a field of lavender.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.
An arched brick corridor leading to a dining area with tables set for a meal.

10. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
  • Float in tuscan splendor with vineyard views from two pools at this wine country hotel.
P23,352
P26,399 total
includes taxes & fees
Nov 3 - Nov 4
Borgo Scopeto Wine & Country Relais
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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 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 4 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 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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