Picnic in Rutland

Self-catering holiday cottages to rent in Rutland

Visit Rutland and stay in high quality self catering holiday cottages - it is only 18 miles by 17 miles big, making it the smallest county in England, but there is plenty of activities for you to enjoy. Rutland is landlocked, bounded to the west and north by Leicestershire, to the northeast by Lincolnshire and the southeast by Northamptonshire. There are two main towns in Rutland are Oakham, the county town, and Uppingham. At the centre of the county is Rutland Water, a large artificial reservoir that is an important nature reserve. Many parents who live abroad visit their children at boarding school in this area and rent self-catering holiday cottages. Half-terms can therefore get booked up quickly! Holiday properties large and small for the perfect break, well equipped with everything that you need, it is a 'turn key' holiday solution for staying in idyllic settings in beautiful locations. Browse the list of properties below - last minute discounted rates will be shown if applicable.

Sitting-out-area | Stable Cottage, Oakham

Stable Cottage, Rutland

Cottage for hire in Oakham with 2 bedrooms, sleeps 4. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Winter Short Breaks.

Luxury property set in 100 acres of land close to Rutland Water.

  • Horse Riding Nearby
  • Romantic Getaways
  • Rural Location
  • Decorated at Christmas
  • WiFi
  • Luxury Collection
  • Fishing Nearby/On-site
  • Newly Listed Property
  • English Country Cottages
  • Open Plan
  • Accessible Cottages
  • Walk-in Shower/Bath
  • Entrance Ramp/Level Access
  • Parking - On Site
  • Shower Cubicle
  • Last Minute Breaks
  • Country Cottages
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Stunning grade II listed detached thatched holiday cottage | Dick’s Cottage, Cottesmore, near Oakham

Dicks Cottage, Rutland

Large holiday house in Cottesmore, near Oakham with 4 bedrooms, sleeps 8. Pets welcome. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Short Breaks All Year.

This chocolate box cottage with its thatched roof and two living rooms is the perfect location to enjoy a countryside break.

  • Barbecue
  • Bike Store
  • Detached Property
  • Rural Location
  • Thatched Roof
  • Decorated at Christmas
  • WiFi
  • Baby and Toddler Friendly
  • Fishing Nearby/On-site
  • Pet Friendly
  • Welcome Cottages
  • Flexi Cottages
  • Parking - On Site
  • Customers Choice
  • Great Value Properties
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Delightful, Grade II listed, thatched stone cottage | Tom Cottage, Wing, near Oakham

Tom Cottage, Rutland

Pet welcome holiday in Wing, near Oakham with 3 bedrooms, sleeps 6. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Short Breaks All Year.

Relax and unwind at this lovely holiday property by the wood-burning stove, or venture further afield and enjoy the Rutland countryside.

  • Barbecue
  • Satellite TV
  • Thatched Roof
  • Woodburning Stove
  • WiFi
  • Baby and Toddler Friendly
  • Luxury Collection
  • Fishing Nearby/On-site
  • Pet Friendly
  • English Country Cottages
  • Flexi Cottages
  • Parking - On Site
  • Shower Cubicle
  • Country Cottages
  • Winter Best Sellers
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Stunning surrounding countryside | Fairchild’s Barn, Big Drift Barn - Fairchilds, Caldecott, near Uppingham

Fairchilds Barn, Rutland

Large house to rent in Caldecott, near Uppingham with 4 bedrooms, sleeps 8. Pets welcome. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Hot Tubs, Short Breaks All Year, Hot Tubs - Private.

With stunning views of the rolling Rutland countryside, Fairchild’s Barn is perfect for a group getaway, ideally located close to an abundance of charming towns.

  • Grouped Properties
  • Rural Location
  • Woodburning Stove
  • Decorated at Christmas
  • WiFi
  • Luxury Collection
  • Working Farm
  • Pet Friendly
  • Newly Listed Property
  • English Country Cottages
  • Open Plan
  • Accessible Cottages
  • Ground Floor Wet Room
  • Walk-in Shower/Bath
  • Entrance Ramp/Level Access
  • Flexi Cottages
  • Parking - On Site
  • Shower Cubicle
  • Last Minute Breaks
View Property Details
Beautiful rural surroundings | Big Drift Barn, Fairchild’s Barn - Fairchilds, Caldecott, near Uppingham

Big Drift Barn, Rutland

Cottage for large groups in Caldecott, near Uppingham with 4 bedrooms, sleeps 8. Pets welcome. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Hot Tubs, Short Breaks All Year, Hot Tubs - Private.

This modern barn conversion can be booked with neighbouring property, Fairchild’s Barn, to accommodate up to sixteen guests, perfect for a group getaway to Rutland.

  • Grouped Properties
  • Rural Location
  • Woodburning Stove
  • Decorated at Christmas
  • WiFi
  • Luxury Collection
  • Working Farm
  • Pet Friendly
  • Newly Listed Property
  • English Country Cottages
  • Open Plan
  • Accessible Cottages
  • Ground Floor Wet Room
  • Walk-in Shower/Bath
  • Entrance Ramp/Level Access
  • Flexi Cottages
  • Parking - On Site
  • Shower Cubicle
  • Last Minute Breaks
View Property Details
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Holiday in Rutland