Vacation rentals in Montepulciano, Italy - page 2

Carefully selected & verified rentals in Montepulciano, Italy
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Check-out
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Rooms and Guests2 Guests, 1 Room
Montepulciano is home to attractions like the Piazza Grande, historic vineyards of Avignonesi, and stunning views from the Fortezza Medicea. The area offers a mix of accommodations, from quaint vacation rentals near Cantina del Redi to charming agriturismos with local culinary experiences. Each stay is handpicked based on guest reviews and great amenities, bringing exclusive options that enhance your Italian experience. Booking during the spring or fall can save you money, and consider renting a bike to explore the hills and vineyards.
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21-40 out of 119
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  • Price: high to low
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Mery'S House Montepulciano
Map500 yd from City Centre900 yd from Palazzo Cervini
FromUS$ 414 /nightSelect
-Casina Vitty- Apartment Montepulciano
MapQuiet area in city center0m
  • Private entrance for enhanced privacy
  • Fully equipped kitchen with modern appliances
  • Close proximity to city center attractions
  • Free parking
  • Flat-screen TV
  • Private terrace
Boutique hotel offering comfortable, well-equipped rooms
FromUS$ 128 /nightSelect
Appartamento Centro Storico La Pulcianella Con Vista Mozzafiato
Map600 yd from City Centre200 yd from Palazzo Cervini
FromUS$ 144 /nightSelect
Contucci Residenze D'Epoca
2 adults
1 bedroom
1 bed
MapRight at the main square100m
  • Centrally located with parking options
  • Rooms feature a kitchenette and flat-screen TV
  • Adjacent to Cantine Contucci winery tastings
  • Free parking
  • Kitchenette
  • Flat-screen TV
Charming hotel with historic character and local wine tastings
FromUS$ 196 /nightSelect
La Casina In Via Fiorita
MapClose to attractions300m
  • Private entrance for added privacy
  • Air-conditioned rooms with modern amenities
  • Well-equipped kitchen for self-catering
  • Air conditioning
  • Fully equipped kitchen
  • Private entrance
Boutique hotel featuring self-catering rooms and privacy
FromUS$ 190 /nightSelect
Palazzo Colombi
4 adults
2 bedrooms
2 beds
MapQuiet area inside the historic quarter250m
  • Historic building with modern amenities
  • Spacious rooms with a fully equipped kitchen
  • On-site coffee shop and family-friendly features
  • On-site coffee shop
  • Family-friendly features
  • 24-hour reception
Hotel featuring unique heritage charm and family-friendly services
FromUS$ 177 /nightSelect
Mezzanino L Palazzo Gagnoni Grugni
4 adults
1 bedroom
3 beds
MapIn the historic center300m
  • Mountain views from private rooms
  • Living space includes a full kitchen
  • Central location in the historic center
  • 24-hour reception
  • Private entrance
  • Kitchen facilities
Charming hotel with private rooms and mountain views
FromUS$ 135 /nightSelect
Truffle House Tuscany Tuber Melanosporum Vitt
MapNearby Terme di Montepulciano4.9km
  • Renovated historic building
  • Fully equipped kitchen
  • Adults only accommodation
  • Flat-screen TV
  • Coffee shop
  • Private entrance
Contemporary apartment hotel in a historical setting
FromUS$ 210 /nightSelect
Il Terrazzino, Piccolo Loft In Montepulciano
MapProximity to Terme di Montepulciano4.9km
  • Private entrance for added privacy
  • Equipped kitchen for self-catering options
  • Flat-screen TV with satellite channels
  • Private terrace
  • Flat-screen TV
  • No smoking
Hotel featuring modern amenities and a secluded loft
FromUS$ 107 /nightSelect
Il Corso
The largest option:
4 adults
2 bedrooms
3 beds
MapNearby Terme di Montepulciano5.3km
  • Family-friendly rooms available
  • Equipped kitchen and dining area
  • Mountain and lake views from rooms
  • Air conditioning
  • Flat-screen TV
  • Outdoor dining
Hotel with picturesque views and family amenities
FromUS$ 232 /nightSelect
La Casina Di Mira
2 adults
1 bedroom
1 bed
MapInner courtyard views0m
  • Private entrance for added privacy
  • Soundproofed rooms for quiet stays
  • Fully equipped kitchen for convenience
  • Flat-screen TV
  • Fully equipped kitchen
  • Air conditioning
Cozy hotel with unique features for leisure travelers
FromUS$ 84 /nightSelect
Truffle House Tuscany Magnatum Pico
MapTerme di Montepulciano4.7km
  • Recently renovated historic building
  • Self-catering rooms with kitchen facilities
  • Shared lounge and kitchen for guests
  • Shared kitchen
  • Air conditioning
  • Flat-screen TV
Charming hotel featuring well-equipped modern rooms
FromUS$ 311 /nightSelect
Amazing Apartment With Swimming Pool, Montepulciano Toscana
Map2.0 mi from City Centre1.0 mi from Montepulciano Terme
FromUS$ 227 /nightSelect
Dimora Dell'Erbe Apartment
The largest option:
6 adults
2 bedrooms
3 beds
Map400 yd from City Centre100 yd from Palazzo Cervini
FromUS$ 481 /nightSelect
Stefania Townhouse
The largest option:
4 adults
2 bedrooms
2 beds
MapClose to Terme di Montepulciano5.7km
  • Historic building with character
  • Bicycle rental and car services available
  • On-site activities like biking and hiking
  • Bicycle rental
  • Car rental
  • Air conditioning
Hotel featuring unique rooms in a historic setting
FromUS$ 130 /nightSelect
Tuscany Apartament
6 adults
3 bedrooms
3 beds
MapProximity to Terme di Montepulciano4.5km
  • Private check-in and check-out available
  • Spacious rooms with terrace views
  • Barbecue facilities in garden area
  • Outdoor dining
  • Garden area
  • Barbecue facilities
Hotel offering spacious rooms with outdoor dining options
FromUS$ 177 /nightSelect
L'Aquila E L'Ulivo
MapNear Terme di Montepulciano6.6km
  • Private pool with lake views
  • Air-conditioned rooms with balconies
  • 24-hour front desk service
  • Private pool
  • Air conditioning
  • Close to attractions
Hotel with private pool and balconies overlooking nature
FromUS$ 333 /nightSelect
Il Giardino Della Fortezza
6 adults
2 bedrooms
3 beds
MapHeart of old town200m
  • Private check-in and check-out available
  • Bicycle rental for cycling enthusiasts
  • Outdoor dining area in the garden
  • Outdoor dining
  • Bicycle rental
  • Children's play area
Hotel offering family-friendly amenities and cycling activities
FromUS$ 275 /nightSelect
Montepulcianolettings " Rooms And Studio "
Map300 yd from City Centre300 yd from Palazzo Cervini
FromUS$ 149 /nightSelect
Palazzo Tombesi Trecci
The largest option:
5 adults
2 bedrooms
3 beds
MapSteps from Val di Chiana300m
  • On-site spa services available
  • Italian cuisine restaurant on-site
  • Cozy dining and seating areas
  • Dining Area
  • On-site Spa
  • Italian Restaurant
Hotel featuring rooms with unique dining areas and spa
FromUS$ 155 /nightSelect

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Check-in
30Jan2026Select date
Check-out
31Jan2026Select date
Rooms and Guests2 Guests, 1 Room