Houses in Uppingham and Apartments – Holiday Lettings - Holiday Rentals Uppingham

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214 Holiday homes

(8) Excellent 

18

Holiday home in Uppingham

Rutland / Uppingham

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £132 / night

£705 - £911 / week

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Responds fast!
avg. 2 hours 5 minutes

from £132 / night

(23) Excellent 

31

Uppingham holiday home rental

Rutland / Uppingham

5 14 2 nights min

  • 5 bedrooms
  • sleeps 14
  • 2 nights min
  • Swimming pool
  • Pet friendly
  • Private garden

from £1,031 / night

£6,183 / week

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from £1,031 / night

(6) Very Good 

14

Cottage rental in Uppingham

Rutland / Uppingham

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £121 / night

£647 - £796 / week

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Responds fast!
avg. 2 hours 5 minutes

from £121 / night

(15) Excellent 

28

Holiday apartment in Uppingham

Rutland / Uppingham

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary

from £109 / night

£573 - £813 / week

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Responds fast!
avg. 1 hour 0 minutes

from £109 / night

(5) Excellent 

15

Holiday apartment in Uppingham

Rutland / Uppingham

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly

from £115 / night

£561 - £642 / week

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from £115 / night

(18) Excellent 

29

Holiday cottage in Uppingham

Rutland / Uppingham

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Private garden

from £114 / night

£596 - £974 / week

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from £114 / night

7

Holiday home in Uppingham

Rutland / Uppingham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden

from £115 / night

£802 / week

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Responds fast!
avg. 1 hour 0 minutes

from £115 / night

26

Holiday home in Uppingham

Rutland / Uppingham

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £52 / night

£904 / week

Enquire View

from £52 / night

Great rentals within 20 miles that match your search

Distance approx 14.75 miles from Uppingham

(30) Excellent 

20

Holiday cottage in Market Harborough

Leicestershire / Market Harborough

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 160 km
  • Child friendly
  • Private garden

from £66 / night

£337 - £481 / week

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Responds fast!
avg. 1 hour 41 minutes

from £66 / night

Distance approx 5.54 miles from Uppingham Show on Map

(33) Excellent 

Certificate of Excellence

18

Holiday cottage in Wakerley

Rutland / Wakerley

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

Certificate of Excellence

from £115 / night

£544 - £802 / week

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from £115 / night

Distance approx 15.96 miles from Uppingham

(7) Very Good 

41

Peterborough holiday home rental

Cambridgeshire / Peterborough

10 20 min stay varies

  • 10 bedrooms
  • sleeps 20
  • min stay varies
  • Nearest beach 65 km
  • Child friendly
  • Pet friendly

from £773 / night

£2,290 - £5,611 / week

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Responds fast!
avg. 3 hours 19 minutes

from £773 / night

Distance approx 6.15 miles from Uppingham Show on Map

(3) Excellent 

20

B&b rental in Barnsdale

Oakham / Barnsdale

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation

from £90 / night

£642 / week

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Responds fast!
avg. 2 hours 9 minutes

from £90 / night

Distance approx 5.57 miles from Uppingham Show on Map

(13) Excellent 

Certificate of Excellence

15

Apartment rental in Oakham

Rutland / Oakham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Private garden

Certificate of Excellence

from £102 / night

£624 - £773 / week

Book View

Responds fast!
avg. 2 hours 59 minutes

from £102 / night

Distance approx 5.14 miles from Uppingham Show on Map

(29) Excellent 

24

Edith Weston holiday cottage rental

Rutland / Edith Weston

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 1 km
  • Suitable for children age 5+
  • Pet friendly

from £100 / night

£475 - £675 / week

Enquire View

from £100 / night

Distance approx 4.87 miles from Uppingham Show on Map

(12) Very Good 

8

North Luffenham holiday home rental

Rutland / North Luffenham

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 5 km
  • Child friendly
  • Pet friendly

from £161 / night

£567 - £659 / week

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Responds fast!
avg. 3 hours 2 minutes

from £161 / night

Distance approx 2.92 miles from Uppingham Show on Map

6

Holiday apartment in Manton, Rutland

Leicestershire / Manton, Rutland

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £138 / night

£516 - £745 / week

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Responds fast!
avg. 2 hours 11 minutes

from £138 / night

Distance approx 3.02 miles from Uppingham Show on Map

5

Holiday cottage in Manton, Rutland

Leicestershire / Manton, Rutland

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £144 / night

£796 / week

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Responds fast!
avg. 2 hours 11 minutes

from £144 / night

Distance approx 5.35 miles from Uppingham Show on Map

(42) Very Good 

29

Holiday cottage in Hambleton

Rutland / Hambleton

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly

from £172 / night

£997 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £172 / night

Distance approx 10.4 miles from Uppingham

(14) Excellent 

18

Holiday cottage in Market Overton

Rutland / Market Overton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden

from £105 / night

£715 - £950 / week

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from £105 / night

Distance approx 3 miles from Uppingham Show on Map

(1) Excellent 

4

Holiday cottage in Manton, Rutland

Leicestershire / Manton, Rutland

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £98 / night

£401 - £630 / week

Book View

Responds fast!
avg. 2 hours 11 minutes

from £98 / night

Distance approx 8.96 miles from Uppingham

(18) Excellent 

Certificate of Excellence

17

Holiday cottage in Cottesmore

Rutland / Cottesmore

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £184 / night

£1,283 / week

Book View

Responds fast!
avg. 2 hours 28 minutes

from £184 / night

Distance approx 2.88 miles from Uppingham Show on Map

(17) Very Good 

Certificate of Excellence

22

Holiday farmhouse in Manton

Oakham / Manton

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

Certificate of Excellence

from £103 / night

£516 - £642 / week

Book View

from £103 / night

Distance approx 5.4 miles from Uppingham Show on Map

(14) Very Good 

8

Holiday cottage letting

Rutland / Wakerley

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £144 / night

£487 - £567 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £144 / night

Distance approx 18.62 miles from Uppingham

5

Melton Mowbray holiday b&b rental

Leicestershire / Melton Mowbray

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly

from £46 / night

£321 / week

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from £46 / night

Distance approx 17.97 miles from Uppingham

22

Holiday apartment in Leicester

Leicestershire / Leicester

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly

from £94 / night

£565 - £1,166 / week

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from £94 / night

Distance approx 17.59 miles from Uppingham

15

Holiday apartment in Leicester

Leicestershire / Leicester

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly

from £126 / night

£882 - £1,844 / week

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from £126 / night

Distance approx 3.04 miles from Uppingham Show on Map

6

Holiday apartment in Manton, Rutland

Leicestershire / Manton, Rutland

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £138 / night

£516 - £745 / week

Book View

Responds fast!
avg. 2 hours 11 minutes

from £138 / night

Distance approx 11.11 miles from Uppingham

12

Holiday home in Stamford

Lincolnshire / Stamford

19 38 min stay varies

  • 19 bedrooms
  • sleeps 38
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £916 / night

£6,412 / week

Book View

Responds fast!
avg. 1 hour 8 minutes

from £916 / night

Distance approx 12.04 miles from Uppingham

(1) Excellent 

12

Holiday log cabin in Oakham

Rutland / Oakham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Private garden

from £134 / night

£710 - £1,203 / week

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from £134 / night

Distance approx 16.2 miles from Uppingham

(2) Very Good 

6

Lodge rental in Market Harborough

Leicestershire / Market Harborough

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly

from £83 / night

£518 / week

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from £83 / night

Distance approx 17.9 miles from Uppingham

8

Apartment letting in Leicester

Leicestershire / Leicester

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min

from £92 / night

£577 / week

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from £92 / night

Distance approx 15.65 miles from Uppingham

45

Holiday guest house rental

Northamptonshire / Kettering

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Private garden

from £91 / night

£401 / week

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Responds fast!
avg. 3 hours 3 minutes

from £91 / night

Distance approx 17.76 miles from Uppingham

7

Leicester holiday apartment rental

Leicestershire / Leicester

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly

from £184 / night

£745 / week

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from £184 / night

Distance approx 17.14 miles from Uppingham

6

Birstall holiday home rental

Leicester / Birstall

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly
  • Private garden

from £229 / night

£1,603 / week

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Responds fast!
avg. 28 minutes

from £229 / night

Distance approx 18.02 miles from Uppingham

22

Apartment rental in Leicester

Leicestershire / Leicester

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly

from £79 / night

£553 / week

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from £79 / night

Distance approx 19.06 miles from Uppingham

23

Leicester holiday apartment rental

Leicestershire / Leicester

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child friendly

from £63 / night

£441 / week

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from £63 / night

Distance approx 6.53 miles from Uppingham Show on Map

5

Holiday cottage with golf nearby in Barnsdale

Oakham / Barnsdale

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min

from £55 / night

£385 / week

Enquire View

from £55 / night

Distance approx 17.58 miles from Uppingham

15

Holiday apartment rental

Leicestershire / Leicester

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly

from £81 / night

£561 / week

Book View

from £81 / night

Distance approx 17.9 miles from Uppingham

8

Apartment letting in Leicester

Leicestershire / Leicester

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly

from £79 / night

£553 / week

Book View

from £79 / night

Distance approx 17.57 miles from Uppingham

31

Holiday cottage in Burton Coggles

Lincolnshire / Burton Coggles

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min

from £101 / night

£707 / week

Enquire View

from £101 / night

Top Destination reviews

Luxury Rutland House. 5 Bedrooms/Pool/Cinema room
Wonderful for a family get together!

So impressed by this house! It was perfect for my 50th birthday family celebration. So much space! Great to have the pool, sauna and hot tub..even the gym facilities and darts were used. The cinema room was brilliant too. So many bathrooms, great cooking facilities, large garden...I really can't fault the house. Katie was really helpful; explaining how to use all the facilities. I would really recommend this place and have great memories now of a fab weekend...thanks!see more
The Corner House, Uppingham, Rutland.
Perfect place to stay

A lovely house right in the centre of Uppingham. The rooms are perfectly furnished to make the stay homely, elegant and comfortable. Great for 3 couples or for a family reunion with small children included. We will be back. … see more
Delightful Ground Floor Apartment
Comfortable apartment in centre of Uppingham

The apartment is in the centre of Uppingham, just minutes walk from shops, pubs and restaurants. We enjoy our stays so much that we never look at other accommodation in the area. Uppingham won a gold medal for flower displays and the Spring flowers were beautiful. Oakham is a pleasant town and a little further is Stamford is beautiful. Rutland is a small but lovely county, 'Much in little'.see more
Little Thatch, Seaton, Uppingham - Thatched Rutland Luxury Holiday Cottage
Delightful Chocolate Box Cottage

What a delightful cottage so quaint and pretty. Thank you to Martin and Julia for creating such gem of a place to stay in. The Kitchen is stocked with every utensil you can think of, there were tea, milk, coffee and luxury biscuits waiting for us on arrival. The cottage is home from home. It is a good base for visiting Rutland Water, Stamford, Oakham, Burleigh House, and Uppingham. Well done Martin and Julia on the presentation of the cottage as a whole.see more

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