Top Hotels with Swimming Pools in Montegrossi

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Our top choices for Montegrossi hotels with a pool

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

1. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Tuscan retreat offers sparkling outdoor pool with free cabanas, loungers, and refreshing poolside bar service.

S$173

includes taxes & fees

6 Oct - 7 Oct

A rectangular swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.

A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

A traditional stone building with a garden featuring geometric hedges and potted plants.

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.

2. 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.

S$302

includes taxes & fees

5 Oct - 6 Oct

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

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.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

3. Agriturismo San Sano

Gaiole in Chianti

Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.

S$140

includes taxes & fees

7 Oct - 8 Oct

A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.

A cozy living room with a fireplace, wooden bookshelves, and a decorative mirror.

A four-poster bed with a view of the outdoors, a desk with a chair, and a sofa in a room with wooden beams on the ceiling.

An indoor dining area with tables set for two, large windows, and potted plants.

4. Villa Sassolini Country Boutique Hotel

Montevarchi

Splash and relax at this Tuscan retreat with dreamy indoor and outdoor pools for any season.

S$321

includes taxes & fees

7 Oct - 8 Oct

5. Relais Santa Cristina

Radda in Chianti

S$159

includes taxes & fees

16 Sept - 17 Sept

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A modern living room with a white sofa, armchairs, and a coffee table.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

6. Chapter Chianti, a Member of Design Hotels

Cavriglia

S$397

includes taxes & fees

6 Oct - 7 Oct

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

A building with arched windows, a courtyard with a pond, and a metal fence.

7. Hotel Casafrassi

Castellina in Chianti

Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.

S$96

includes taxes & fees

11 Sept - 12 Sept

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 spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

An outdoor dining area with a pool, potted plants, and umbrellas.

8. 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.

S$295

includes taxes & fees

8 Oct - 9 Oct

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Choose what matters most at hotels with a pool in Montegrossi

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4 stars

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Hot tub

Spa

Top Montegrossi Hotel Reviews

Borgo Vescine

10/10 Excellent

"This place is simply perfection From the moment you check in to the moment you leave , you feel like royalty . Staff is impressive how polite , accommodating and welcoming Thank you Lorenzo at the bar ! Honestly no words besides EXCELLENT Anna /Canada !!!!"

Villa Pitiana

10/10 Excellent

"We spent our honeymoon here and it was absolutely beautiful"

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The staff were very friendly and helpful. The bar service is the best."

Hotel Athena

10/10 Excellent

"Clean, well located, friendly staff, wonderful views"

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

Dievole Wine Resort

10/10 Excellent

"Amazing hotel with the most unreal views. Staff were super friendly. Would definitely recommend!"

Hotel Italia

10/10 Excellent

"Our stay was fantastic. The room was genuinely luxurious with marble fittings everywhere. The staff were brilliant and really knew what to recommend. The breakfast was good but rather crowded on the day we were there."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

COMO Castello Del Nero

10/10 Excellent

"Great staff!"

Frequently asked questions

What are some hotels with pools in Montegrossi?

La Certosa di Pontignano: Features 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. Grand Hotel Continental Siena – Starhotels Collezione: Provides 2 restaurants, 2 outdoor swimming pools and a full-service spa. Villa Pitiana: Hotel located near Piazza del Campo. Features a sauna, a seasonal outdoor pool and a snack bar/deli. Hotel Chiusarelli: Offers 2 restaurants, a seasonal outdoor pool and a full-service spa.

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 Castello di Albola.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Montegrossi Hotels with Swimming Pools

Our top choices for Montegrossi hotels with a pool

1. Ultimo Mulino Wellness Country Hotel

2. Badia a Coltibuono

3. Agriturismo San Sano

4. Villa Sassolini Country Boutique Hotel

5. Relais Santa Cristina

6. Chapter Chianti, a Member of Design Hotels

7. Hotel Casafrassi

8. Relais Vignale & Spa

9. Borgo Casa al Vento

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

Choose what matters most at hotels with a pool in Montegrossi

Top Montegrossi Hotel Reviews

Borgo Vescine

Villa Pitiana

Villa Scacciapensieri Boutique Hotel

Hotel Athena

Borgo San Felice Resort

Dievole Wine Resort

Hotel Italia

Castello di Spaltenna- Small Luxury Hotels of the World

COMO Castello Del Nero

Frequently asked questions

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