Self catering accommodation in Oakham and cottages – Holiday Lettings - Holiday Rentals Oakham

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  • United Kingdom
  • England
  • Rutland
  • Oakham
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  • Barnsdale (1)
  • Wing (1)

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16 Holiday homes

(1) Excellent 

17

Self Catering Town Centre apartment - Oakham apartment sleeps 4

Rutland / Oakham

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
This beautiful self catering apartment is located in the heart of the town centre of Oakham, Rutland. Accommodation-Living room with sofa bed (sleeps 2) family bathroom, bedroom (kingsize or 2 singles) and kitchen. Perfectly situated just a 2 minute walk from the train  …see more

from £80 / night

£560 / week

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from £80 / night

(13) Excellent 

24

The Chapel - Wing. RUTLAND. - Wing converted chapel sleeps 4

Oakham / Wing

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Ask owner if suitable for children
ABOUT THE CHAPEL: The Chapel, Wing is an early 19th Century stone built Grade II listed Methodist Chapel sympathetically converted at the turn of the 21st Century to create a unique Modernist open plan house. Winner of The George Phillips Award and featured in "Living E  …see more

from £52 / night

£360 - £685 / week

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from £52 / night

(20) Excellent 

14

Sticky End - Thatched Rutland Holiday Cottage - Oakham cottage sleeps 4

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
** Sister property to local Rutland thatched cottages: Little Thatch, Seaton, Near Uppingham, Rutland - Property No. 1130618+Autumn Cottage, Preston, Near Oakham/Uppingham, Rutland - Property No. 6555591NB: All our cottages operate a strictly "Non-smoking" &a  …see more

from £95 / night

£495 - £790 / week

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from £95 / night

(4) Excellent 

14

The Gallery Apartment, Oakham, Rutland - Oakham apartment sleeps 4

Rutland / Oakham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
A newly converted two bedroom self catering apartment situated in the centre of the historic market town of Oakham. The building was converted to an apartment in 2015 and provides accommodation on the first floor with two bedrooms accommodating four guests, a sitting r  …see more

from £85 / night

£535 - £585 / week

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from £85 / night

12

Holiday log cabin with Hot Tub and Sauna 5* Clover - Oakham log cabin sleeps 2

Rutland / Oakham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 6 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard.  …see more

from £111 / night

£620 - £985 / week

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from £111 / night

(3) Excellent 

20

The Walled Garden, Rutland - Barnsdale b&b sleeps 2

Oakham / Barnsdale

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
The Walled Garden Bed and Breakfast is a pretty, self-contained cottage that sits in a quiet, private garden in Barnsdale, in the heart of Rutland. Located just a minute's walk from the banks of Rutland Water, it's perfect for a weekend getaway or longer holiday, ideal  …see more

from £80 / night

£560 / week

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from £80 / night

(12) Excellent 

23

Autumn Cottage - Thatched Rutland Holiday Cottage - Oakham cottage sleeps 4

Rutland / Oakham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Ask owner if suitable for children
  • Private garden
** Sister property to local Rutland thatched cottages: Sticky End, Cottesmore, Near Oakham, Rutland - Property No. 9749 + Little Thatch, Seaton, Near Uppingham, Rutland - Property No. 1130618NB: All our cottages operate a strictly "Non-smoking" & "No  …see more

from £95 / night

£495 - £790 / week

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from £95 / night

(6) Excellent 

7

Laburnum Cottage - Oakham bungalow sleeps 6

Rutland / Oakham

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
  • Private garden
This large bungalow is situated at the end of a shared private cul-de-sac and has a light and airy feel. It has a blend of contemporary and retro style original 60s and 70s fittings and furnishings.Outside there are lawned areas to the front and rear with specimen trees  …see more

from £95 / night

£600 / week

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from £95 / night

11

Holiday log cabin 5* Hot tub and Sauna - Poppy - Oakham log cabin sleeps 2

Rutland / Oakham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 4 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard.  …see more

from £84 / night

£595 - £970 / week

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from £84 / night

10

log cabin with hot tub free fishing Primrose - Oakham log cabin sleeps 4

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 4 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard.  …see more

from £80 / night

£435 - £890 / week

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from £80 / night

8

Modern studio flat in stunning farm location - Oakham apartment sleeps 2

Rutland / Oakham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
The Stables Flat is attached to our secluded farmhouse. We are surrounded by rolling fields grazed by cattle, sheep and horses. We keep pigs, ducks and hens. The house is down a quiet country lane without passing cars, apart from farm traffic. The light, airy flat has  …see more

from £65 / night

£290 / week

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from £65 / night

(7) Excellent 

14

The Green, Rutland holiday cottage - Oakham cottage sleeps 5

Rutland / Oakham

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Private garden
The Green is a self-catering Rutland holiday cottage in the rural conservation village of Market Overton just a stone’s throw away from Rutland Water. Rutland is excellent for walking and cycling and The Green holiday cottage provides a perfect base for exploring the  …see more

from £120 / night

£715 / week

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from £120 / night

(2) Excellent 

19

Orchard House, Newly Built Modern county House - Oakham house sleeps 9

Rutland / Oakham

3 9 2 nights min

  • 3 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Available for Burghley horse trails This newly built house can sleep up to 9 people. This house is perfect for a family weekend away, perfect open plan kitchen to meals in or BBQ outside.  Orchard House is a beautiful luxury architect designed home in Rutland. Buil  …see more

from £400 / night

£2500 / week

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from £400 / night

(1) Excellent 

10

Holiday lodge with Hot Tub and Sauna 5* Waterlily - Oakham log cabin sleeps 2

Rutland / Oakham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 6 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard.  …see more

from £111 / night

£620 - £985 / week

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from £111 / night

20

44489 Cottage in Rutland - Oakham house sleeps 6

Rutland / Oakham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
CHARMING COTTAGE OFFERING A RELAXING COUNTRYSIDE BREAK This semi-detached property is situated in the heart of an active working family farm. With the owners various breeds of cows located in the surrounding fields, and the beautiful rolling countryside as a backdrop  …see more

from £55 / night

£385 - £840 / week

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from £55 / night

18

Rutland / Oakham

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Car not necessary

 …see more

from £60 / night

£420 / week

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from £60 / night

Top Destination reviews

Orchard House, Newly Built Modern county House
Lovely spacious but cosy house for a weekend away

We stayed at Orchard House for a weekend away for a friend's hen do. We had an excellent stay in the house, felt really comfortable and was very easy to get around (although we only went as far as Rutland water!). Rooms were all very spacious, partic … see more
Sticky End - Thatched Rutland Holiday Cottage
charming, well equipped cottage in the heart of Rutland

The cottage was charming from the moment we opened the gate into the front yard, which was a real sun trap and haven of glorious plants. The cottage itself was beautifully furnished, outstandingly equipped and very comfortable. We had a most enjoyabl … see more
The Chapel - Wing. RUTLAND.
Amazing bolt hole in a super location

Everything about the chapel was brilliant. The warm welcome from the neighbors (hello Kev … see more

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