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.

Gated entrance | Old Barn, North Luffenham, near Oakham

Old Barn, Rutland

Big family holiday house to rent in North Luffenham, near Oakham with 4 bedrooms, sleeps 8. No pets allowed. Enclosed Garden/Patio, Golf nearby, Pub within 1 mile, Short Breaks All Year.

Old Barn is a beautiful barn conversion located in the Rutland countryside, perfect for a group getaway.

  • Detached Property
  • Woodburning Stove
  • WiFi
  • Luxury Collection
  • Newly Listed Property
  • English Country Cottages
  • Parking - On Site
  • Shower Cubicle
  • Last Minute Breaks
  • Country Cottages
  • GroupB
  • GroupH
  • GroupT
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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.

  • Bike Store
  • Detached Property
  • Rural Location
  • Thatched Roof
  • Decorated at Christmas
  • WiFi
  • Baby and Toddler Friendly
  • Fishing Nearby/On-site
  • Welcome Cottages
  • Flexi Cottages
  • Parking - On Site
View Property Details
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
  • Thatched Roof
  • Woodburning Stove
  • WiFi
  • Baby and Toddler Friendly
  • Luxury Collection
  • Fishing Nearby/On-site
  • English Country Cottages
  • Flexi Cottages
  • Parking - On Site
  • Shower Cubicle
  • Summer Best Sellers
  • Country Cottages
  • Winter Best Sellers
View Property Details
Exterior | Game Cottage, Mushroom Cottage - Normanton Park Cottages, Normanton, near Oakham

Game Cottage, Rutland

Small cosy holiday cottage in Normanton, near Oakham with 1 bedroom, sleeps 1. Pets welcome. Golf nearby, Pub within 1 mile, Short Breaks All Year.

With beautiful views over Rutland Water this cosy cottage is ideal for enjoying sailing, windsurfing or a pleasure cruise on the water.

  • Ground Floor Facilities
  • Grouped Properties
  • Fishing Nearby/On-site
  • Newly Listed Property
  • Welcome Cottages
  • All En-suite
  • Open Plan
  • Parking - On Site
  • Shower Cubicle
  • Lakeside
  • Waterside Breaks
View Property Details
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
  • GroupB
  • GroupH
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
  • GroupB
  • GroupH
View Property Details
Kitchen/diner | Shepherd’s Cottage - Gunthorpe, Gunthorpe, near Oakham

Shepherds Cottage Uk, Rutland

Pet friendly holiday in Gunthorpe, near Oakham with 2 bedrooms, sleeps 4. Golf nearby, Short Breaks All Year.

With views over Rutland Water, this luxury cottage has two en-suite bedrooms and lies 2 miles from the market town of Oakham.

  • Grouped Properties
  • Rural Location
  • Woodburning Stove
  • WiFi
  • Luxury Collection
  • Working Farm
  • Pet Friendly
  • Newly Listed Property
  • English Country Cottages
  • All En-suite
  • Accessible Cottages
  • Entrance Ramp/Level Access
  • Flexi Cottages
  • Parking - On Site
  • Shower Cubicle
  • Last Minute Breaks
  • Country Cottages
  • GroupB
  • GroupH
  • GroupT
View Property Details
Stylishly furnished open plan living space | Keeper’s Cottage - Gunthorpe, Gunthorpe, near Oakham

Keepers Cottage Uk, Rutland

Dog friendly weekend break in Gunthorpe, near Oakham with 2 bedrooms, sleeps 4. Golf nearby, Short Breaks All Year.

This wonderful cottage has a feature roll-top bath and a dressing room, and you can enjoy a plethora of water sports on nearby Rutland Water.

  • Grouped Properties
  • Rural Location
  • WiFi
  • Luxury Collection
  • Working Farm
  • Pet Friendly
  • Newly Listed Property
  • English Country Cottages
  • All En-suite
  • Open Plan
  • Accessible Cottages
  • Entrance Ramp/Level Access
  • Flexi Cottages
  • Parking - On Site
  • Shower Cubicle
  • Last Minute Breaks
  • Country Cottages
  • GroupB
  • GroupH
  • GroupT
View Property Details
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Holiday in Rutland