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.

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.

Stunning grade II listed detached thatched holiday cottage | Dick’s Cottage, Cottesmore, near Oakham

Great quality

Dicks Cottage, Rutland

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

  • 4 Pets welcome
  • Enclosed Garden/Patio
  • Golf nearby
  • Pub within 1 mile
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Highchair
  • Rural Location
  • Stairgate
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Cot Available
  • Washing Machine
View Property Details

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.

Delightful, Grade II listed, thatched stone cottage | Tom Cottage, Wing, near Oakham

High standard

Tom Cottage, Rutland

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

  • 2 Pets welcome
  • Enclosed Garden/Patio
  • Golf nearby
  • Pub within 1 mile
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Highchair
  • Stairgate
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Cot Available
  • Luxury Collection
  • Washing Machine
View Property Details

Cottage with dogs allowed in Cottesmore, near Oakham with 2 bedrooms, sleeps 4. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Short Breaks All Year.

Exterior | Well Cottage, Cottesmore, near Oakham

Well equipped

Well Cottage, Rutland

A perfect escape in the countryside in this stunning Grade II listed thatched cottage.

  • 2 Pets welcome
  • Enclosed Garden/Patio
  • Golf nearby
  • Pub within 1 mile
  • Short Breaks All Year
  • Dishwasher
  • Fuel and Power Included
  • Highchair
  • Rural Location
  • Stairgate
  • Television
  • WiFi
  • Bed Linen & Towels Included
  • Cot Available
  • Washing Machine
View Property Details

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.

Beautiful rural surroundings | Big Drift Barn, Fairchild’s Barn - Fairchilds, Caldecott, near Uppingham

Exceptional

Big Drift Barn, Rutland

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

  • 2 Pets welcome
  • Enclosed Garden/Patio
  • Golf nearby
  • Pub within 1 mile
  • Hot Tubs
  • Short Breaks All Year
  • Hot Tubs - Private
  • Dishwasher
  • Fuel and Power Included
  • Grouped Properties
  • Rural Location
  • Television
  • WiFi
  • Bed Linen Included
  • Luxury Collection
  • Washing Machine
View Property Details
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Holiday in Rutland