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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 41 Cottages in Trespiano with updated reviews, rates, and availability.

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Outdoor pool

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle

9.6 out of 10, Exceptional, (19)
"More than we imagined for our Tuscany vacation. Spacious, well appointed and clean. Marzio was an excellent host with knowledge of the area and its history. He gave wonderful suggestions for wines, restaurants and touring excursions. We highly recommend this historical villa for a Tuscany vacation!"
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Typical Tuscan Countryside Cottage near Florence
Property grounds

Typical Tuscan Countryside Cottage near Florence

10.0 out of 10, Exceptional, (26)
"We really enjoyed our stay and we can highly recommend this lovely cottage."
Typical Tuscan Countryside Cottage near Florence
Happy holidays in Chianti, among olives and vineyards, From Florence
Property grounds

Happy holidays in Chianti, among olives and vineyards, From Florence

9.8 out of 10, Exceptional, (16)
"A lovely little cottage in beautiful surroundings and perfectly situated to discover Tuscany. Elisabeth is lovely and very friendly and helpful and Oliver is brilliant"
Happy holidays in Chianti, among olives and vineyards, From Florence
Charming Farmhouse with Private Pool among Vineyards
Aerial view

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (50)
"We stayed here with our family as a large group of 8 adults and 1 infant. The layout of the house worked great, each couple had their own room (even our daughter) and their own bathroom! Our daughter loved the pool and the property had everything we needed. The location was great, our group took day trips to explore Siena, Florence, and wine country. The winery on the property was also fantastic! A great place to say and I highly recommend it!"
Charming Farmhouse with Private Pool among Vineyards
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Outdoor pool

Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities

9.8 out of 10, Exceptional, (31)
"Most beautiful and quiet setting. Awesome host. I would have given 5 stars across the board but the property is fairly remote down a rough gravel road, but definitely worth the drive for the location and host."
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Stone cottage on heritage Chianti estate-pool-tennis
Pool

Stone cottage on heritage Chianti estate-pool-tennis

Stone cottage on heritage Chianti estate-pool-tennis
Villa Vestra in Vinci holiday home
Exterior detail

Villa Vestra in Vinci holiday home

10.0 out of 10, Exceptional, (13)
"It was great to be in the free standing house and beautiful garden of Silvia and Guliano. These hosts are very kindly and make you feel welcome. All is compleet and proper. The terraces are on different places in the garden and from there is a nice view around"
Villa Vestra in Vinci holiday home
Typical country house with garden near Florence Siena Pisa San Gimignano
Outdoor dining

Typical country house with garden near Florence Siena Pisa San Gimignano

9.6 out of 10, Exceptional, (48)
"We enjoyed some days in this beautiful area"
Typical country house with garden near Florence Siena Pisa San Gimignano
Belvilla by OYO Cottage in Tavarnelle With Garden
Cottage | Pool | Outdoor pool

Belvilla by OYO Cottage in Tavarnelle With Garden

Belvilla by OYO Cottage in Tavarnelle With Garden
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Exterior

La Quercia, apartment with garden for 6/8 people in the heart of Chianti

10.0 out of 10, Exceptional, (2)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
Outdoor pool

Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two

9.8 out of 10, Exceptional, (10)
"To start we were welcomed by a complimentary bottle of wine to celebrate our new marriage! The host was very attentive, provided restaurant recommendations, wine tour suggestions and local site seeing suggestions. Apartment was clean and cozy with spectacular views with olive trees and host made olive oil! This host goes above and beyond to make their guests feel at home. By far our favourite part of our week was Nelson…. You stole my heart out handsome guard dog. We will 100% be back and...
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
Belvilla by OYO Cottage in Tavarnelle with Garden
Pool

Belvilla by OYO Cottage in Tavarnelle with Garden

Belvilla by OYO Cottage in Tavarnelle with Garden
Il Melograno, Chianti apartment in farmhouse for 4 people with garden
Outdoor dining

Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Il Melograno, Chianti apartment in farmhouse for 4 people with garden
Holiday house in the countryside near Florentine museums
Exterior

Holiday house in the countryside near Florentine museums

Holiday house in the countryside near Florentine museums
Our charming Tuscan Cottage
Exterior

Our charming Tuscan Cottage

Our charming Tuscan Cottage
Small stone cottage in the woods, artists retreat, with pool
Oven

Small stone cottage in the woods, artists retreat, with pool

10.0 out of 10, Exceptional, (29)
"Rustieke oude boerderij op een heuveltop. De weg ernaartoe gaat met een aantal haarspeldbochten op een onverharde eigen weg. Complex is opgedeeld in een woonhuis voor de eigenaars en daarbij wat vroeger wellicht schuren of stallen waren voor de verhuur. Ontzettend aardige verhuurders, contact verloopt soepel, netjes. Midden in de natuur. Heel nice"
Small stone cottage in the woods, artists retreat, with pool
Casa Palmira - Country House
Outdoor dining

Casa Palmira - Country House

Casa Palmira - Country House
Cottage - The Hill Below - Imagine a place just for you
Outdoor pool

Cottage - The Hill Below - Imagine a place just for you

Cottage - The Hill Below - Imagine a place just for you
Belvilla by OYO La Villa
House | Dining

Belvilla by OYO La Villa

Belvilla by OYO La Villa
Aurora, 3 bedroom house with air conditioning, wifi, garden and shared pool
Fridge, oven, stovetop, dishwasher

Aurora, 3 bedroom house with air conditioning, wifi, garden and shared pool

Aurora, 3 bedroom house with air conditioning, wifi, garden and shared pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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