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Sep 30 - Oct 1
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Oct 1 - Oct 2
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Our top choices for Ossaia hotels

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 poolside dining setup with tables and chairs, a pool, and a sunset in the background.
A courtyard with a brick building, surrounded by well-maintained lawns and potted plants.

1. Borgo Tre Rose

Borgo Tre Rose
Montepulciano
United States
Nathan
CA $113
CA $131 total
includes taxes & fees
Oct 23 - Oct 24
Borgo Tre Rose
A dining area with a table and chairs, large windows with curtains, and a view of a landscape.
A balcony with two lounge chairs, a small table with a drink, and a scenic view.
A hotel room with a large bed, a bedside table with a lamp, a mirror, and a framed picture on the wall.
A reception area with a wooden console table, two wall clocks, and a staircase leading to an upper level.

2. Hotel San Luca

Hotel San Luca
Cortona Old Town
Ireland
Mariusz
CA $114
CA $139 total
includes taxes & fees
Oct 28 - Oct 29
Hotel San Luca
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 cobblestone street with terracotta planters and a sign indicating the location of the Chiesa di San Francesco.
A wooden staircase with a handrail on both sides, leading to an upper floor.

3. B&B San Francesco

B&B San Francesco
Cortona Old Town
United Kingdom
Esther
CA $108
CA $149 total
includes taxes & fees
Oct 1 - Oct 2
B&B San Francesco
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 swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.

4. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
United States
Peter
CA $181
CA $212 total
includes taxes & fees
Oct 7 - Oct 8
Relais Villa Baldelli
A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.
A spacious living room with a yellow sofa, a wooden coffee table, and a floral rug. There are two armchairs and a dining table with chairs. The room has a large window with curtains, a mirror, and wall-mounted lights.
A hotel room with a fireplace, two armchairs, a bed, and a dresser.
A table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

5. Hotel Villa Marsili

Hotel Villa Marsili
Cortona Old Town
United States
fares
CA $228
CA $264 total
includes taxes & fees
Oct 10 - Oct 11
Hotel Villa Marsili
A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.
A balcony with potted plants and a view of the sea.
A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.
A spacious room with a fireplace, multiple seating areas, and large windows allowing natural light.

6. Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town
United States
George F
CA $153
CA $176 total
includes taxes & fees
Oct 2 - Oct 3
Villa Santa Margherita
A stone building with outdoor seating and a fountain.
A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.
A stone building with multiple windows and a courtyard.
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.

7. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
Canada
Olga
CA $160
CA $189 total
includes taxes & fees
Oct 12 - Oct 13
Villa Borgo San Pietro
A terrace with sun loungers, stone walls, and potted plants.
A pool area with lounge chairs, a hot tub, and a view of mountains.
A narrow hallway with a stone wall and a clock.
A spacious lobby with a high ceiling, a grand chandelier, and a staircase leading to an upper level.

8. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
United Kingdom
Alexander
CA $386
CA $437 total
includes taxes & fees
Oct 25 - Oct 26
Monastero di Cortona Hotel & Spa
A couple in a hot tub with a cityscape view through large windows.
A balcony with terracotta pots of flowers, a view of a rural landscape, and a stone building with a tiled roof.
A room with a large window, a vase of red flowers, and a white umbrella outside.
A bathroom with a bathtub, a table with a vase of flowers, and a view of the countryside through a window.

9. Hotel San Michele

Hotel San Michele
Cortona Old Town
United States
Tala
CA $218
CA $252 total
includes taxes & fees
Oct 14 - Oct 15
Hotel San Michele
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.
A cozy living room with a fireplace, a sofa, a dining table, and various decorative items.

10. Locanda del Molino

Locanda del Molino
Cortona
Canada
Rochelle
CA $110
CA $134 total
includes taxes & fees
Oct 27 - Oct 28
Locanda del Molino
A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.
A bedroom with a stone wall, a bed with a headboard, a desk with a computer, a chair, a window with a view, and a ceiling with exposed beams.
A historic stone building with a sign reading "Hotel Italia."
A lobby with a reception desk, a fireplace, and a large arched doorway leading outside.

11. Hotel Italia

Hotel Italia
Cortona Old Town
United States
Frances
CA $172
CA $197 total
includes taxes & fees
Oct 13 - Oct 14
Hotel Italia
A waterfront hotel with a swimming pool, a boat dock, and a view of the water.
A hotel room with a bed, a desk with a lamp, a TV, and a window with a view of the sea.
A waterfront hotel with multiple balconies, a calm river, and a dock with boats.
A waterfront restaurant with outdoor seating, a view of a river, and buildings in the background.

12. Hotel Lidò

Hotel Lidò
Passignano sul Trasimeno
United States
Brian
CA $145
CA $166 total
includes taxes & fees
Oct 5 - Oct 6
Hotel Lidò
A swimming pool with a brick wall and metal railings, surrounded by blooming flowers and a yellow building with a tiled roof.
A residential area with a swimming pool, a yellow building with a tiled roof, and a hill with a church in the background.
A kitchen with wooden cabinets, a dining table with chairs, a window with curtains, and a radiator.
A hotel room with a bed, a desk, and a chair. There are two windows with views of greenery and a building.

13. Villaggio Albergo Le Macerine

Villaggio Albergo Le Macerine
Contrada Fontivegge
United Kingdom
ROBERT
CA $146
CA $167 total
includes taxes & fees
Oct 11 - Oct 12
Villaggio Albergo Le Macerine
A historic building with a courtyard, surrounded by lush greenery and trees.
A bedroom with a bed, bedside lamps, a window, and a rustic wooden ceiling.
A living room with a sofa, two armchairs, a floor lamp, a radiator, a window with curtains, a cabinet, and framed pictures on the wall.
A well-maintained garden with tall cypress trees, a lawn, and a building with a tiled roof.

14. Equo Suites

Equo Suites
Castiglione del Lago
Australia
Alistair
CA $180
CA $204 total
includes taxes & fees
Oct 6 - Oct 7
Equo Suites
A nighttime swimming pool area with lounge chairs and umbrellas, surrounded by stone buildings and trees.
A neatly made bed with a headboard, two bedside tables, and a wall-mounted artwork.
A restaurant with wooden beams, large windows with white curtains, and multiple seating areas.
Villa Paradiso with a stone wall entrance, a metal gate, and a signboard.

15. Hotel Villa Paradiso

Hotel Villa Paradiso
Passignano sul Trasimeno
United States
Maria
CA $112
CA $130 total
includes taxes & fees
Oct 7 - Oct 8
Hotel Villa Paradiso
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.
A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.

16. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
United States
Dana
CA $219
CA $249 total
includes taxes & fees
Oct 7 - Oct 8
Cortona Resort - Le Terre Dei Cavalieri
An outdoor dining area with round tables, white chairs, and a variety of dishes and drinks.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with two round tables and wicker chairs.
A rectangular swimming pool with a stone border, surrounded by a grassy lawn and trees.
A two-story building with a flat roof and a covered front porch. There are two visible windows on the upper floor and a door on the ground floor.

17. Park Hotel Montigeto

Park Hotel Montigeto
Passignano sul Trasimeno
United Kingdom
Helen
CA $131
CA $148 total
includes taxes & fees
Oct 7 - Oct 8
Park Hotel Montigeto
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 poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A bedside table with a vase of flowers, a book, and a drawer.

18. Locanda agli Amici

Locanda agli Amici
Cortona
United Kingdom
David
CA $141
CA $168 total
includes taxes & fees
Oct 13 - Oct 14
Locanda agli Amici
Restaurant
Exterior
Reception
Front of property

19. Agriturismo Parco Fiorito

Agriturismo Parco Fiorito
Tuoro sul Trasimeno
Brazil
Anonymous traveller
CA $162
CA $246 total
includes taxes & fees
Oct 22 - Oct 23
Agriturismo Parco Fiorito
A cozy wooden cabin room with a bed, pillows, a TV, and a view of the outdoors.
A gravel pathway flanked by neatly trimmed hedges leading to a gate.
A modern indoor pool area with wooden benches, a hot tub, and large windows offering views of the surrounding greenery.
A buffet with various food items and a mirror reflecting the room's architecture.

20. I Capricci di Merion Resort & Spa

I Capricci di Merion Resort & Spa
Tuoro sul Trasimeno
United States
Israel
CA $246
CA $271 total
includes taxes & fees
Oct 5 - Oct 6
I Capricci di Merion Resort & Spa
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Top Ossaia Hotel Reviews

Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Todo estuvo perfecto, el hotel muy muy lindo, la piscina extraordinaria, la habitación Muy cómoda, el servicio impecable, pero no funcionó el wifi en la habitación. No nos dieron un early check in ni guardaron las maletas, así que nos tuvimos que ir a Montslcino y ya no pudimos usar la piscina. Pero en general lo recomiendo mucho"
Patricia 1-night trip
Posted 1 day ago
Nuovo Etruria Resort
Villa Tiberini Wine Relais

Villa Tiberini Wine Relais

10/10 Excellent
"It's great place for the large family."
ENLI 3-night trip
Posted 2 days ago
Villa Tiberini Wine Relais
Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"We had a lovely 5 night stay at La Sovana in their apartment complex. We had a 2-bedroom, 2-bath with kitchen. It was the perfect set up for 2 couples to share. My only wish was that it included a washer/dryer set up. Laundry is available for a fee which we did use but it would be nice if there was washing capability in the apartment itself. The staff were super helpful, the property is clean and well maintained. The food in the restaurant is very good as well. We would definitely return to La Sovana."
Stephanie 5-night trip
Posted 3 days ago
Agriturismo La Sovana
Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."
Julio 1-night trip
Posted 3 days ago
Hotel Villa Ricci
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"In addition to the property being absolutely beautiful, the"
Michele 3-night trip
Posted 4 days ago
Relais Villa Grazianella - UNA Esperienze
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Great location, nice vineyards right out the door, lots of great restaurants nearby."
Lisa 2-night trip
Posted 5 days ago
Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 10 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

10/10 Excellent
"buenas vistas panorámicas , es un hotel demasiado tranquilo , pero es muy bonito"
Enzo 2-night trip
Posted 11 days ago
Hotel Panoramic Montepulciano
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"Amazing stay for our 25th anniversary. The property is breathtaking and every corner was like a Tuscan postcard! The room was beautiful, the pools were great and the food was exceptional. Would highly recommend and would go back in a second!"
Teri 2-night trip
Posted 12 days ago
Il Falconiere - Relais e Chateaux

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
CA $161
CA $183 total
Oct 22 - Oct 23
includes taxes & fees
9.4/10 Exceptional! (211 reviews)
Hotel La Terrazza di Montepulciano
Locanda Granducato

Locanda Granducato

località paccianese 48 Chiusi SI
CA $185
CA $207 total
Oct 5 - Oct 6
includes taxes & fees
7/10 Good! (2 reviews)
Locanda Granducato
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
Hotel Sangallo

Hotel Sangallo

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

Residence Peloni

Via Polidori 50 Arezzo AR
Get ratesResidence Peloni
Agriturismo Godiolo

Agriturismo Godiolo

VIA DI MARTIENA 24 Montepulciano SI
Get ratesAgriturismo Godiolo

Frequently asked questions

What is the best area to stay in Ossaia?
The best area to stay in Ossaia is the area immediately surrounding the main piazza, as this is where you'll find the heart of the village.This central part of Ossaia is compact and easily walkable, with the piazza serving as a focal point for village life. You'll find a few local shops and eateries here, and it's where residents gather. The historic church is also located just off the piazza, adding to the village's character.For couples looking for a romantic escape, staying in a converted farmhouse or villa just outside the village centre offers a truly authentic Tuscan experience. These properties often provide stunning views of the rolling hills and olive groves, and many come with private pools, allowing for a secluded and relaxing retreat.
When is the best time to go to Ossaia?
The best time to visit Ossaia, and Tuscany generally, is during the spring (April to June) and autumn (September to October) months. These periods offer pleasant weather and a less crowded experience.For those planning a romantic getaway or a relaxed trip, spring is particularly lovely. The countryside is lush and green, wildflowers are in bloom, and the temperatures are comfortably warm without being too hot. This is a great time for leisurely drives through the vineyards, enjoying al fresco dining, and visiting local markets.Couples looking for a culinary focus might prefer autumn. This season brings the grape harvest, truffle hunting season, and olive oil production, offering unique gastronomic experiences.
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 Ossaia.
How much is the nightly rate at a Ossaia hotel?
Prices for hotels in Ossaia often vary, but you can find a great deal from CA $130 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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