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Oct 2 - Oct 3
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Oct 3 - Oct 4
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Oct 2 - Oct 4
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Oct 9 - Oct 11

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Our top choices for Santa Maria hotels

A swimming pool with lounge chairs and umbrellas, surrounded by a well-maintained hedge and a stone building in the background.
A spacious living area with a fireplace, wooden beams, and a staircase.
A kitchen with wooden cabinets, a stove, a refrigerator, and a window.
An outdoor dining table set with plates, cutlery, wine, and a vase of flowers, surrounded by a lush garden and tall trees.

1. Agriturismo Casal Gheriglio

Agriturismo Casal Gheriglio
Lucignano
$171 nightly
$188 total
Oct 9 - Oct 10
Total with taxes and fees
Agriturismo Casal Gheriglio
An outdoor dining area with tables and chairs under canopies, surrounded by greenery and a building with a tiled roof.
A room with a wooden desk, a laptop, a chair, a sofa, and a small table with a bowl of fruit and flowers.
A large outdoor swimming pool with multiple lanes and a surrounding deck area.
A conference room with a long table, black chairs, a red curtain backdrop, and wall-mounted lighting.

2. Hotel Apogeo

Hotel Apogeo
Sinalunga
Canada
Jason
$99 nightly
$112 total
Oct 9 - Oct 10
Total with taxes and fees
Hotel Apogeo
A stone building with multiple windows and a central entrance.
A terrace with a sofa and cushions, overlooking a cityscape and mountains.
A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.
A dining area with a table set for two, white chairs, and a stone-patterned floor.

3. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
Canada
Heather
$69 nightly
$76 total
Oct 5 - Oct 6
Total with taxes and fees
Fondaco del Moro
A room with a piano, stone walls, a wooden cabinet, and a bench.
A dining area with a yellow table, white chairs, and a kitchen in the background.
A bedroom with a bed, a nightstand, a potted plant, and a window with a view.
A narrow stairway with a small window overlooking a courtyard with a brick building and a wooden ceiling.

4. Antico Granaione

Antico Granaione
Rapolano Terme
United States
Irene
$87 nightly
$100 total
Nov 2 - Nov 3
Total with taxes and fees
Antico Granaione
A stone building with a courtyard and a canal.
A bar area with wooden shelves, books, and a brick wall. There are three green bar stools and a patterned rug on the floor.
A bedroom with a wooden ceiling, a bed with a decorative headboard, a bench, and a large wardrobe.
A stone patio with a round table and chairs, surrounded by potted plants, overlooking a hilly landscape.

5. Palazzo Brandano

Palazzo Brandano
Trequanda
United Kingdom
Andrew
$93 nightly
$106 total
Nov 2 - Nov 3
Total with taxes and fees
Palazzo Brandano
An outdoor patio area with wicker furniture, a table, and a lamp.
A room with a white counter, a bowl of fruit, a plant in a gold pot, and a mirror reflecting a plant and a window with curtains.
A bar area with a variety of liquor bottles, a pizza on a wooden board, and three martini glasses with straws.
A hallway with a wooden floor, a small table with a vase, and a light fixture on the ceiling.

6. Il Monte

Il Monte
Monte San Savino
United States
Thomas
$89 nightly
$102 total
Oct 16 - Oct 17
Total with taxes and fees
Il Monte
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.
A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.
An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.

7. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
United States
Jinhee
$150 nightly
$171 total
Oct 5 - Oct 6
Total with taxes and fees
Cortona Resort - Le Terre Dei Cavalieri
An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.
A window with a view of a green landscape, a table with a teapot, cups, and a tray of snacks.
A bedroom with a large bed, wooden headboard, a chandelier, a nightstand, and a red rug.
An outdoor dining area with string lights, tables set for a meal, and a natural backdrop.

8. Podere La Rocca

Podere La Rocca
Montepulciano
Canada
Jake
$156 nightly
$176 total
Oct 22 - Oct 23
Total with taxes and fees
Podere La Rocca
A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.
An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.
A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.
A restaurant interior with tables set for dining, a kitchen area, and a wine display.

9. Hotel Le Capanne

Hotel Le Capanne
Arezzo
United States
Ronilynn
$106 nightly
$123 total
Oct 18 - Oct 19
Total with taxes and fees
Hotel Le Capanne
A restaurant with glass walls, tables set with white tablecloths, and chairs.
A skylight with a view of a tree and a distant building.
A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.
A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.

10. La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
United Kingdom
Ronald
$94 nightly
$110 total
Oct 12 - Oct 13
Total with taxes and fees
La Cantina Relais - Fattoria Il Cipresso
A cozy room with a fireplace, two armchairs, and a table.
A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.
An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.

11. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
United States
Robert
$224 nightly
$251 total
Oct 24 - Oct 25
Total with taxes and fees
Tenuta Santo Pietro
An outdoor dining area with a table set with food and wine, surrounded by outdoor seating and a large house in the background.
A restaurant with round tables set for dining, large windows with curtains, and a view of the countryside.
A courtyard with a brick building, surrounded by well-maintained lawns and potted plants.
A pool surrounded by neatly trimmed hedges and a row of sun loungers.

12. Borgo Tre Rose

Borgo Tre Rose
Montepulciano
United States
Nathan
$72 nightly
$84 total
Nov 2 - Nov 3
Total with taxes and fees
Borgo Tre Rose
A table set with a bottle of wine, two wine glasses, and a vase with flowers.
A hotel room with a bed, a sofa, a chair, a small table with a lamp, and a window with a view of a green landscape.
A cozy living room with a sofa, armchair, and a coffee table with a vase.
A living room with a sofa, armchair, and a wooden cabinet.

13. Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
United Kingdom
Giulio
$209 nightly
$234 total
Nov 2 - Nov 3
Total with taxes and fees
Poggio Paradiso Resort & Spa
A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.
A hallway with a decorative archway leading to a door, a row of plants on the left, and a wall-mounted lamp on the right.
A rooftop terrace with outdoor seating, a pergola, and a view of hills.
A spa area with a circular hot tub surrounded by mosaic tiles, a stone bench, and a small table with a bowl and a candle.

14. Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
Arezzo
United States
Luis Mauricio
$73 nightly
$87 total
Oct 12 - Oct 13
Total with taxes and fees
Il Gentiluomo Hotel & SPA
A modern hotel lobby with a reception desk, seating area, and a large plant.
A hotel with a modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.
A hotel with a rooftop pool, a modern building with a sloped roof, and a view of the surrounding town.
A modern bar area with a counter, bar stools, and a seating area with chairs.

15. Hotel Park

Hotel Park
Castiglion Fiorentino
United States
Karen
$106 nightly
$121 total
Oct 8 - Oct 9
Total with taxes and fees
Hotel Park
A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.
A restaurant with a high ceiling, brick walls, and a bar area with a variety of bottles. There are tables and chairs for dining, and a television is visible on the right side.
A bedroom with a bed, a sofa, a desk, and a TV. There are windows with curtains and a view of greenery outside.
A historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.

16. Hotel Borgo Antico

Hotel Borgo Antico
Monteroni d'Arbia
United Kingdom
Charles
$94 nightly
$109 total
Oct 31 - Nov 1
Total with taxes and fees
Hotel Borgo Antico
A rustic outdoor dining area with stone walls, a table, and wicker chairs.
A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.
A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.
A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

17. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
United States
Peter
$140 nightly
$164 total
Oct 7 - Oct 8
Total with taxes and fees
Relais Villa Baldelli
A stone building with outdoor seating and a fountain.
A stone building with multiple windows and a courtyard.
A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.
A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.

18. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
Canada
Olga
$107 nightly
$127 total
Oct 5 - Oct 6
Total with taxes and fees
Villa Borgo San Pietro
A brick building with a sign reading "SVETONI Wine Resort" at its entrance.
A hotel room with a large bed, a bedside table with a lamp, a bench, and framed pictures on the wall.
A rectangular swimming pool with a well-maintained lawn and lounge chairs around it.
A room with a large window, a chair, a small table, and a mirror.

19. Villa Svetoni Wine Resort

Villa Svetoni Wine Resort
Montepulciano
United States
Julia
$251 nightly
$281 total
Oct 18 - Oct 19
Total with taxes and fees
Villa Svetoni Wine Resort
A villa with a swimming pool, outdoor seating, and a tennis court.
A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.
A pool area with lounge chairs and umbrellas, a stone planter with flowers, and a building with balconies in the background.
An aerial view of a property with a swimming pool, tennis court, and vineyard.

20. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
United States
Deanna
$110 nightly
$125 total
Oct 31 - Nov 1
Total with taxes and fees
Villa Curina Resort
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Top Santa Maria Hotel Reviews

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Beautiful property in the middle of a vineyard! Relaxing."
Kimberly 2-night trip
Posted 1 hour ago
Precise Tale Poggio Alla Sala
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"We had an amazing stay at Monastero di Cortona Hotel & Spa. The property is absolutely beautiful, but what really stood out was the staff. Everyone went above and beyond to make sure we were taken care of and had everything we needed. A special thank you to the team for helping arrange our truffle lunch and wine tour, both were wonderful experiences and made our time in Tuscany even more memorable. The breakfast was top notch, the spa was excellent, and the overall level of service was outstanding. Alessandro was excellent, but there were so many wonderful staff members who contributed to making our stay so special."
Steve 5-night trip
Posted 4 hours ago
Monastero di Cortona Hotel & Spa
Palazzo Brandano

Palazzo Brandano

10/10 Excellent
"Bello lugar, bella vista panoramica. Hay que trasladarse para comer a pueblos vecinos próximos."
Barbara 1-night trip
Posted 22 hours ago
Palazzo Brandano
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"All good"
Leo 4-night trip
Posted 2 days ago
Hotel San Gregorio
Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Great big room with excellent amenities. Wonderful staff."
Nasser 1-night trip
Posted 2 days ago
Nuovo Etruria Resort
Albergo Le Terme

Albergo Le Terme

10/10 Excellent
"It was amazing."
PAUL 3-night trip
Posted 2 days ago
Albergo Le Terme
Palazzuolo

Palazzuolo

10/10 Excellent
"Excellent room, good location, the staff is very gentle, the breakfast is good"
Nami 2-night trip
Posted 3 days ago
Palazzuolo
Villa Tiberini Wine Relais

Villa Tiberini Wine Relais

10/10 Excellent
"It's great place for the large family."
ENLI 3-night trip
Posted 4 days ago
Villa Tiberini Wine Relais
L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"Tout etait parfais. Chambre propre, staff accueillants et disponible au besoin. Petit déjeuner tres bon avec beaucoup de choix de qualité. Location et vue incroyable. Paysage a couper le souffle."
elise 2-night trip
Posted 6 days ago
L'Orto delle Terme

More cheap stays in Santa Maria

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
$112 nightly
$128 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (211 reviews)
Hotel La Terrazza di Montepulciano
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
$152 nightly
$173 total
Oct 20 - Oct 21
Total with taxes and fees
Castello di Bossi
La Locanda di Casalmustia

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI
Get rates
8.6/10 Excellent! (44 reviews)
La Locanda di Casalmustia
Tenuta La Pieve Casale Presciano

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR
Get ratesTenuta La Pieve Casale Presciano
Tenuta La Pieve Casale La Valle

Tenuta La Pieve Casale La Valle

Via Giovanni XXII Pergine Valdarno AR
Get ratesTenuta La Pieve Casale La Valle
Hotel Sangallo

Hotel Sangallo

Via Dei Fiori 30 Montepulciano SI
Get rates
8/10 Very Good! (59 reviews)
Hotel Sangallo

Frequently asked questions

What is the best area to stay in Santa Maria?
The best area to stay in Santa Maria is the historic center, particularly around Piazza della Repubblica and the main Corso.This central area is the heart of Santa Maria, characterized by its narrow, winding streets, historic architecture, and a lively pedestrian-friendly environment. You'll find a good selection of traditional trattorias, local shops, and cafes clustered around the main square and along the Corso. It's an excellent base for experiencing the town's local life.For couples seeking a romantic and convenient stay, the historic center is ideal. Its charming lanes are great for evening strolls, and many accommodations are within renovated historic buildings, offering a unique local experience. You'll be steps away from local eateries and cultural points of interest.Travelers looking for a tranquil retreat with easy access to the Tuscan countryside will find the areas just outside the historic center, particularly those offering agriturismo stays, to be a wonderful choice.
When is the best time to go to Santa Maria?
The best time to go to Santa Maria, Tuscany, is during the spring (April to June) and fall (September to October) for pleasant weather and fewer crowds.During spring, the countryside is lush and green, with wildflowers blooming. Temperatures are mild, typically ranging from 60°F to 75°F, making it ideal for exploring vineyards, hiking, and enjoying outdoor dining without the intense summer heat. This period is excellent for couples who want to experience the scenic beauty of Tuscany and participate in activities like wine tours and cooking classes.Fall offers similarly comfortable temperatures, usually between 65°F and 70°F, and the landscape transforms with rich autumnal colors. This season is particularly appealing for food and wine enthusiasts, as it coincides with grape harvests and truffle hunting season.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Santa Maria.
How much is the nightly rate at a Santa Maria hotel?
Prices for hotels in Santa Maria often vary, but you can find a great deal from $76 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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