Hotels in Santa Maria

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Where to stay in Santa Maria?

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.

An outdoor dining table set with plates, cutlery, wine, and a vase of flowers, surrounded by a lush garden and tall trees.

A rustic kitchen with wooden cabinets, a fireplace, and a dining area with a table and chairs.

1. Agriturismo Casal Gheriglio

Lucignano

$169

$197 total

includes taxes & fees

Nov 3 - Nov 4

An outdoor dining area with tables and chairs under canopies, surrounded by greenery and a building with a tiled roof.

A conference room with a long table, black chairs, a red curtain backdrop, and wall-mounted lighting.

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.

2. Hotel Apogeo

Sinalunga

$99

$111 total

includes taxes & fees

Oct 18 - Oct 19

A stone building with multiple windows and a central entrance.

A terrace with a sofa and cushions, overlooking a cityscape and mountains.

A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.

A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.

3. Fondaco del Moro

Civitella in Val di Chiana

$68

$75 total

includes taxes & fees

Oct 18 - Oct 19

A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.

A restaurant interior with tables set for dining, a kitchen area, and a wine display.

4. Hotel Le Capanne

Arezzo

$106

$123 total

includes taxes & fees

Oct 25 - Oct 26

A room with a piano, stone walls, a wooden cabinet, and a bench.

A narrow stairway with a small window overlooking a courtyard with a brick building and a wooden ceiling.

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.

5. Antico Granaione

Rapolano Terme

$89

$102 total

includes taxes & fees

Nov 1 - Nov 2

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

Monte San Savino

$73

$112 total

includes taxes & fees

Oct 24 - Oct 25

A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.

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.

A modern hotel lobby with a large mirror, potted plants, and a spacious seating area.

7. Il Gentiluomo Hotel & SPA

Arezzo

$72

$86 total

includes taxes & fees

Oct 25 - Oct 26

A stone building with a courtyard and a canal.

A stone patio with a round table and chairs, surrounded by potted plants, overlooking a hilly landscape.

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 spacious room with a large bed, two armchairs, a sofa, and a view of the outdoors through a large window.

8. Palazzo Brandano

Trequanda

$69

$79 total

includes taxes & fees

Nov 4 - Nov 5

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 traditional room with a fireplace, wooden furniture, and a large mirror.

An outdoor dining area with string lights, tables set for a meal, and a natural backdrop.

9. Podere La Rocca

Montepulciano

$183

$206 total

includes taxes & fees

Oct 24 - Oct 25

A table set with a bottle of wine, two wine glasses, and a vase with flowers.

A living room with a sofa, armchair, and a wooden cabinet.

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.

An open door leading to a balcony with a stone wall and a view of a landscaped garden.

10. Poggio Paradiso Resort & Spa

Torrita di Siena

$234

$262 total

includes taxes & fees

Nov 8 - Nov 9

A restaurant with glass walls, tables set with white tablecloths, and chairs.

A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.

A long dining table set with plates, glasses, and floral centerpieces, surrounded by chairs.

A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.

11. La Cantina Relais - Fattoria Il Cipresso

Arezzo

$96

$113 total

includes taxes & fees

Oct 19 - Oct 20

A modern hotel lobby with a reception desk, seating area, and a large plant.

A modern bar area with a counter, bar stools, and a seating area with chairs.

A hotel with a rooftop pool, a modern building with a sloped roof, and a view of the surrounding town.

A modern library with leather sofas, bookshelves, and a large window.

12. Hotel Park

Castiglion Fiorentino

$106

$121 total

includes taxes & fees

Oct 25 - Oct 26

A brick building with a sign reading "SVETONI Wine Resort" at its entrance.

A room with a large window, a chair, a small table, and a mirror.

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.

13. Villa Svetoni Wine Resort

Montepulciano

$206

$232 total

includes taxes & fees

Oct 18 - Oct 19

An outdoor dining area with a table set with food and wine, surrounded by outdoor seating and a large house in the background.

A courtyard with a brick building, surrounded by well-maintained lawns and potted plants.

A poolside dining setup with tables and chairs, a pool, and a sunset in the background.

A restaurant with round tables set for dining, large windows with curtains, and a view of the countryside.

14. Borgo Tre Rose

Montepulciano

$73

$85 total

includes taxes & fees

Nov 2 - Nov 3

A cozy room with a fireplace, two armchairs, and a table.

A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

15. Tenuta Santo Pietro

Pienza

$257

$287 total

includes taxes & fees

Oct 20 - Oct 21

A rustic brick wall with a lantern and a metal archway overlooking a lush valley.

A rural estate with traditional stone buildings, a swimming pool, and expansive views of the countryside.

A bedroom with a stone wall, a bed with teal bedding, a chandelier, and a view through a glass door.

An outdoor pool area with a fountain, string lights, and stone walls.

16. LaChiusa Tuscany

Torrita di Siena

$223

$250 total

includes taxes & fees

Nov 11 - Nov 12

A person in a white robe standing by a window with a view of mountains.

A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.

A couple dining at a table with a scenic view of mountains and a lake.

A bedside table with a vase of flowers, a book, and a drawer.

17. Locanda agli Amici

Cortona

$97

$115 total

includes taxes & fees

Oct 24 - Oct 25

A narrow street with a yellow building on the left, a wooden structure in the background, and a row of white and pink flowers along the edge.

A hallway with arched ceilings, framed pictures on the walls, and a staircase leading to another room.

A building entrance with the name "ALBERGO LA TERRAZZA" above a wooden door.

A bicycle with potted plants attached to it, parked against a textured wall.

18. Hotel La Terrazza di Montepulciano

Montepulciano

$112

$128 total

includes taxes & fees

Oct 18 - Oct 19

A villa with a swimming pool, terraced garden, and a view of distant mountains.

A fire pit with burning logs, surrounded by stone blocks and a metal grill.

A stone building with a gravel pathway leading to the entrance.

A stone building with a tiled roof, surrounded by a grassy area and flowering plants.

19. Agriturismo Il Macchione

Pienza

$149

$168 total

includes taxes & fees

Nov 10 - Nov 11

A courtyard with stone buildings, a gravel path, and potted plants.

A view through a window of a courtyard with a stone building, a clock tower, and a garden with a geometric flower bed.

A bedroom with a wooden headboard, two beds with pink and white bedding, a bedside table with a lamp, a small table with a bottle and glasses, and a window with a view of buildings.

A cobblestone street with terracotta planters and a sign indicating the location of the Chiesa di San Francesco.

20. B&B San Francesco

Cortona Old Town

$81

$110 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Go beyond your typical stay in Santa Maria

Pet friendly

Apartment

Apart hotel

Spa

Pool

Hot tub

Family friendly

Farm

Check out reviews of Santa Maria hotels guests love

Hotel San Gregorio

10/10 Excellent

"Get"

L'Orto delle Terme

10/10 Excellent

"Clean room and beautiful Suite. Breakfast was excellent!"

Hotel Villa Ricci

8/10 Good

"Bien situe Bon déjeuner"

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"

Hotel Continentale

10/10 Excellent

"The location of this hotel is excellent!"

Il Gentiluomo Hotel & SPA

10/10 Excellent

"It was perfect….the outside was a little run down but the inside was perfect. They had just moved and not cleaned up so that did not help the appearance."

Palazzo Brandano

10/10 Excellent

"Large rooms, helpful staff, delicious breakfast at a very reasonable price. There’s no water by the hotel, as seen in the picture. It’s located on a very old walled town… quite quaint."

Casanova - Panoramic Rooms and Suites

8/10 Good

"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"

Relais Cloister Pienza

10/10 Excellent

"Just a fantastic place in the most beautiful setting. Medieval historical ambiance with a modern vibe. Pool area - perfect. Breakfast - perfect. Dinner - perfect. Views - incredible! Location - the best in town!"

Frequently asked questions

What hotels do travelers like in Santa Maria?

Guests like Villa Tiberini Wine Relais and Palazzo Brandano.

Can I book a refundable hotel in Santa Maria?

If you want the flexibility to change your plans to Santa Maria, most hotels provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Santa Maria be like during my vacation?

The warmest months in Santa Maria are usually August and July with an average temp of 71°F. January and February are the chilliest months when the average temp is 42°F. The rainiest months are November and October.

Why should I book my Santa Maria accommodation with Hotels.com?

There are plenty of reasons to book your Santa Maria travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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