Self catering holiday cottages to rent in Oakham, Rutland, England

The county town of Rutland is Oakham, a thriving settlement in the East Midlands of England which is surrounded by beautiful countryside. It is a fantastic place in which to take a cottage break as there is so much to do in this gorgeous traditional market town, from soaking up culture in the Rutland County Museum and Oakham Castle to a spot of shopping in the Farmers’ Market. There are lots of lovely holiday cottages available in Oakham so that you and your loved ones can be assured of plenty of choice when it comes to exploring this stunning part of the UK.


About Cottage Breaks in Oakham

Choices of self-catering accommodation include country cottages near Oakham as well as options such as dog-friendly cottages and luxury accommodation.

Oakham is just to the west of Rutland Water Nature Reserve which is a man-made lake with small areas of forestry and lots of wetland. It is a Site of Special Scientific Interest and home to the Anglian Water Bird Watching Centre as there are plenty of species that can be found, such as the Tufted Duck, Osprey, Goldeneye and Great Crested Grebe. In August each year it hosts the British Birdwatching Fair. As well as being a haven for birds, Rutland Water is also a popular place for watersports activities and is a great place for chilling out whilst on a cottage holiday. Visitors can go sailing on the lake or walk and cycle along the perimeter of it, and there is even a cruiser, the Rutland Belle, that takes passengers on a relaxing trip around the lake.

Oakham Castle should definitely be visited if staying in the town although only the great hall still remains of this Norman structure. Dating from around 1180, the hall is a Grade I listed building with a stunning interior, decorated with Romanesque details and interestingly, hundreds of horseshoes hanging from the walls. The outer bailey of the castle is a park today with pretty flowerbeds, a kid playground and a bandstand and is lovely place to go for an afternoon picnic whilst on a cottage break in Oakham.

The fantastic Farmers’ Market comes to Oakham every third Saturday of the month and there are stalls selling quality local produce for those wishing to purchase tasty goods to bring home to friends or to use for cooking in self-catering accommodation. It is a brilliant market steeped in tradition and history.

Oakham is home to an array of shops, restaurants, bars and pubs, with friendly locals at every turn. Those who love the great outdoors can go on one of the many walking trails around the town including the Oakham Heritage Trail which gives an insight into the history of this fascinating settlement in the heart of Rutland. Although Oakham doesn’t have its own tourist information centre (the nearest is at Stamford), it does have a Visitor Centre which you can visit for lots of free information. With so much to recommend it, Oakham could be a great choice for a family self-catering holiday or a romantic break away.

Book a Oakham cottage and look forward to discovering some of the best of Rutland on holiday.

20 rental properties
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Price from £635
Next available 04/09 to 09/09/22
no booking fee
sleeps 2 - 5 guests 2 - 5
3 bedrooms 3
2 bathrooms 2
no dogs allowed
5 star

3 bedroom Thatched Cottage

Picture-perfect 2 bedroom, 2 bathroom thatched holiday cottage with country views, private enclosed garden and access to free fishing at nearby Stretton Lakes fishing lakes, all just 6 miles from Rutland Water.

Facilities & Features: Gold Award Winning CottageTVFree Wifi
Price from £3500
Next available 03/07 to 08/07/22
no booking fee
sleeps 4 - 8 guests 4 - 8
4 bedrooms 4
3 bathrooms 3
dog-friendly cottage, 2 dog(s) welcome2

4 bedroom Farmstay

Stylish pet-friendly four bedroom barn conversion with country views and warm bubbly hot tub, just 7 miles from Rutland Water.

Facilities & Features: TVFree WifiOutdoor Hot Tub
Price from £2800
Next available 07/08 to 12/08/22
no booking fee
sleeps 8 - 16 guests 8 - 16
8 bedrooms 8
6 bathrooms 6
dog-friendly cottage, 2 dog(s) welcome2

8 bedroom Group Accommodation

Two stylish barn conversions set next to fields and farmlands, which together sleep up to 16 people in Rutland, each barn has an inviting warm bubbly hot tub and lovely countryside views.

Facilities & Features: TVFree WifiOutdoor Hot Tub
Price from £2800
Next available 31/07 to 05/08/22
no booking fee
sleeps 2 - 8 guests 2 - 8
4 bedrooms 4
3 bathrooms 3
dog-friendly cottage, 2 dog(s) welcome2

4 bedroom Barn Conversion

Stylish 4 bedroom barn conversion with country views and outdoor hot tub, near Rutland Water, (additional barn next door can also be rented by arrangement).

Facilities & Features: TVFree WifiOutdoor Hot Tub
This owner/agency is showing availability but has not provided full pricing information.
Price from £520
Next available 18/07 to 25/07/22
sleeps 2 - 2 guests 2 - 2
1 bedrooms 1
1 bathrooms 1
no dogs allowed
4 star

1 bedroom Farmstay

Fabulous romantic cottage, 4 star rated with its own secluded private hot tub, spoil the one you love on a special break to remember.

Facilities & Features: Digital TVFree WifiOutdoor Hot Tub
This owner/agency is showing availability but has not provided full pricing information.
Price from £830
Next available 26/09 to 07/10/22
sleeps 2 - 6 guests 2 - 6
3 bedrooms 3
3 bathrooms 3
no dogs allowed
4 star

3 bedroom Cottage

Fantastic rural retreat, this family-friendly self-catering farmhouse enjoys a tranquil setting in Leicestershire and with views of the surrounding countryside, high quality accommodation, a gold award, a private hot tub and half an acre of gardens, has plenty to recommend it.

Facilities & Features: Gold Award Winning CottageTVFree WifiGames roomOutdoor Hot Tub
This owner/agency is showing availability but has not provided full pricing information.
Price from £800
Next available 15/07 to 22/07/22
sleeps 1 - 9 guests 1 - 9
4 bedrooms 4
3 bathrooms 3
no dogs allowed

4 bedroom Rural Retreat

Relax and unwind in the Leicestershire countryside at this 4 bedroom family-friendly rural retreat in the Vale of Belvoir near Melton Mowbray, with a private indoor heated swimming pool (with exclusive use by guests) and sauna on offer, this is a great place for a relaxing self-catering holiday, either with family or friends (hen party and stag party groups welcome).

Facilities & Features: TVFree WifiSaunaHeated pool
Sorry, this owner/agency has not provided availability information.
Price from £750
Special Offer 09/07 to 14/07/22
sleeps 2 - 5 guests 2 - 5
3 bedrooms 3
1 bathrooms 1
dog-friendly cottage, 2 dog(s) welcome2

3 bedroom Thatched Cottage

Beautiful 3 bedroom pet-friendly white washed thatched cottage just 5 minutes drive from Rutland Water.

Facilities & Features: TVFree Wifi
Sorry, this owner/agency has not provided availability and full price information.
Price from £575
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
no dogs allowed

1 bedroom Barn Conversion

Romantic rural retreat in Rutland, ideal for a couple, with stunning country views, just 5 miles from Rutland Water.

Facilities & Features: Digital TVFree Wifi
Sorry, this owner/agency has not provided availability and full price information.
Price from £175
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1
3 star

2 bedroom Holiday Lodge

Welcoming 2 bedroom pet-friendly lakeside lodge, set by a fishing lake in Leicestershire, less than 3 miles from Market Harborough.

Facilities & Features: TV
Sorry, this owner/agency has not provided availability and full price information.
Price from £1495
sleeps 7 - 14 guests 7 - 14
4 bedrooms 4
2 bathrooms 2
dog-friendly cottage, 2 dog(s) welcome2
4 star

4 bedroom Large country house

Idyllic 4 bedroom country cottage with inglenook fireplace, plenty of rustic charm and pretty garden, just 2 miles from the fine town of Stamford and just a short drive from Rutland Water Nature Reserve.

Facilities & Features: TVFree WifiOutdoor Hot Tub
Sorry, this owner/agency has not provided availability and full price information.
Price from £1155
sleeps 1 - 5 guests 1 - 5
2 bedrooms 2
1 bathrooms 1
no dogs allowed

2 bedroom Wooden Holiday Lodge

Get away from it all for a fishing holiday or a relaxing rural retreat break to this stylish 2 bedroom wooden holiday lodge in the Vale of Belvoir, just 15 minutes drive from Melton Mowbray, this lodge with its lake views over the fishing lake and south facing veranda is a real treat.

Facilities & Features: TV
Sorry, this owner/agency has not provided availability and full price information.
Price from £650
sleeps 1 - 9 guests 1 - 9
4 bedrooms 4
2 bathrooms 2
dog-friendly cottage, 2 dog(s) welcome2
3 star

4 bedroom Cottage

With dreamy countryside views, a large garden and a location within the Chater Valley, this 4 bedroom country cottage in Rutland has plenty to recommend it for a rural retreat break.

Facilities & Features: TV
Sorry, this owner/agency has not provided availability and full price information.
Price from £2195
sleeps 12 - 20 guests 12 - 20
5 bedrooms 5
3 bathrooms 3
dog-friendly cottage, 3 dog(s) welcome3

5 bedroom Cottage

Beautiful high quality holiday farmhouse with lovely gardens, hot tub and fantastic location next to stunning countryside, just 10 minutes drive from Stamford and Rutland Water Nature Reserve, ideal for large groups such as hen parties or large families.

Facilities & Features: TVFree WifiOutdoor Hot Tub
Sorry, this owner/agency has not provided availability and full price information.
Price from £500
sleeps 1 - 6 guests 1 - 6
3 bedrooms 3
1 bathrooms 1
no dogs allowed

3 bedroom Holiday Lodge

Escape for a rural retreat break at this picture-perfect family-friendly 3 bedroom holiday lodge, nestled by unspoilt Leicestershire countryside close to Market Harborough, this is excellent walking country and some fantastic attractions for days out include Leicesters National Space Centre not too far away and further afield Warwick is within an hours drive.

Facilities & Features: TVFree Wifi
* Price quoted is not inclusive of any applicable booking fees or local charges.