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Hotels with Pool & Resorts in Montegrossi from NZ$151

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Check availability on Montegrossi Hotels with Pool

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Montegrossi hotels with a pool

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
A stone building with a garden, tall trees, and a clear blue sky.
A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

1. 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.
NZ$670
includes taxes & fees
30 Oct - 31 Oct
Castello di Spaltenna- Small Luxury Hotels of the World
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

2. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
NZ$542
includes taxes & fees
6 Oct - 7 Oct
Chapter Chianti, a Member of Design Hotels
A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.
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 outdoor dining area with tables and chairs, overlooking a scenic view of a coastal town during sunset.
A cozy living room with a fireplace, wooden bookshelves, and a decorative mirror.

3. Villa Sassolini Country Boutique Hotel

Villa Sassolini Country Boutique Hotel
Montevarchi
  • Splash and relax at this Tuscan retreat with dreamy indoor and outdoor pools for any season.
NZ$426
includes taxes & fees
11 Oct - 12 Oct
Villa Sassolini Country Boutique Hotel
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 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.

4. 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.
NZ$371
includes taxes & fees
25 Oct - 26 Oct
Palazzo Leopoldo Dimora Storica & Spa
A swimming pool with a view of a historic building surrounded by olive trees.
An outdoor café with tables and chairs, surrounded by stone walls and greenery.
A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.
A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

5. 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.
NZ$319
includes taxes & fees
30 Sept - 1 Oct
Castello di Meleto
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.
A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.
A modern bathroom with a freestanding bathtub, a vanity with a mirror, and marble walls.

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.
NZ$308
includes taxes & fees
25 Oct - 26 Oct
Hotel Palazzo San niccolò & Spa
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.

7. 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.
NZ$294
includes taxes & fees
29 Oct - 30 Oct
Castello di Tornano Wine Resort
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
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.
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

8. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
  • Tuscan retreat offers sparkling outdoor pool with free cabanas, loungers, and refreshing poolside bar service.
NZ$181
includes taxes & fees
25 Oct - 26 Oct
Ultimo Mulino Wellness Country Hotel
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A stone building with multiple windows and a well-lit entrance.
A pathway leading to a pool area with lounge chairs and umbrellas.
A stone building with a clear view of a lush green landscape, including trees and a distant mountain range.

9. Le Lappe

Le Lappe
Cavriglia
  • Rustic farmstay boasts seasonal outdoor pool with loungers and views of Tuscan countryside.
NZ$848
includes taxes & fees
12 Oct - 13 Oct
Le Lappe
A rectangular swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.
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.
A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

10. 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.
NZ$338
includes taxes & fees
27 Oct - 28 Oct
Badia a Coltibuono
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Choose what matters most at hotels with a pool in Montegrossi

Breakfast included
4 stars
5 stars
Spa pool
Spa

Top Montegrossi Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Excellent location with free. And easy parking. Great breakfast, extremely kind and helpful staff, small but adequate shower. Would definitely stay here in the future!!"
Lynne 3-night trip
Posted 4 days ago
Hotel Athena
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent
"Beautiful hotel that is close to a bus line to get into the city. The views and accommodations make this a wonderful place to stay."
Heather 6-night trip
Posted 4 days ago
Villa Ermellina Siena, a Tribute Portfolio Hotel
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 5 days ago
Villa Pitiana
Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem."
Federica 1-night trip
Posted 13 days ago
Villa Scacciapensieri Boutique Hotel
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 2 weeks ago
Hotel Italia
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."
Lauren 3-night trip
Posted 3 weeks ago
COMO Castello Del Nero

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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