Cottages in Uppingham and houses – Holiday Lettings - Holiday Rentals Uppingham

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Uppingham

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8 Holiday homes

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(1) Excellent 

15

Holiday apartment in Uppingham

Rutland / Uppingham

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
This delightful two bedroomed apartment is situated in the centre of Uppingham with everything within walking distance. One double room, one twin room, lounge, bathroom and fully fitted kitchen. Parking space for one car and WIFI. Fully equipped. Richil House was built  …see more

from £100 / night

£490 / week

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from £100 / night

(5) Very Good 

13

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
Moss Cottage is an ideal base to explore the activities in and around Uppingham which itself is an historic Market Town boasting fine Restaurants, Pubs and Bistros all within walking distance of Moss Cottage. The Town of Stamford is not to be missed and only 20 minutes  …see more

from £115 / night

£485 - £665 / week

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from £115 / night

(10) Excellent 

30

Leicestershire and Rutland holiday home rental

Rutland / Uppingham

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Pet friendly
  • Private garden
“Fab weekend away” I had a lovely stay at pinfold house for my friends hen do- the bedrooms were lovely and the big open kitchen/ diner made it easy to entertain.  …see more

from £800 / night

£5600 - £7000 / week

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from £800 / night

(7) Very Good 

23

Holiday apartment in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask owner if suitable for children
A spacious and elegant apartment on the middle floor of a Grade II listed Georgian house. The apartment is minutes away from the Market Place; it is in a peaceful location and so handy for all that Uppingham has to offer: great restaurants, lots of independent retailers  …see more

from £100 / night

£595 - £900 / week

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from £100 / night

(3) Very Good 

16

Holiday home in Uppingham

Rutland / Uppingham

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
“Homely and luxurious rolled into one” Corner House was the perfect place for our long weekend stay at Uppingham. We arrived on a cold January day and immediately felt so welcomed in, as the house was warm and inviting - like going into a friend's hous  …see more

from £115 / night

£545 - £675 / week

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from £115 / night

(16) Excellent 

24

Holiday cottage in Leicestershire and Rutland

Rutland / Uppingham

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask owner if suitable for children
  • Private garden
“Perfect place for a quiet, luxurious holiday” My husband and I have just returned from a week at Little Thatch and it was just perfect. Martin welcomed us with a tour of the house including tips on where to watch out for the low celings - there are m  …see more

from £71 / night

£495 - £825 / week

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from £71 / night

12

Holiday cottage in Leicestershire and Rutland

Rutland / Uppingham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Suitable for children age 5+
  • Private garden
This detached cottage in Uppingham sleeps seven people in three bedrooms.  …see more

from £54 / night

£372 - £793 / week

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from £54 / night

9

Holiday cottage in Uppingham

Rutland / Uppingham

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
Stunning cottage in rural Preston village in between oakham and Uppingham. Two double bedrooms with pretty patio area and kitchen diner ideal for entertaining. 5 minute drive from Rutland water, and 20 minutes drive from stamford. The charming cottage happily sleeps fou  …see more

from £75 / night

£465 / week

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from £75 / night

Top Destination reviews

The Corner House, Uppingham, Rutland.
Homely and luxurious rolled into one

Corner House was the perfect place for our long weekend stay at Uppingham. We arrived on a cold January day and immediately felt so welcomed in, as the house was warm and inviting - like going into a friend's house! The mix between the antique furnit … see more
Luxury Rutland House. 6 Bedrooms/Pool/Cinema room
What more could you want from a hen?

With 7 bridesmaids, 1 heavily pregnant and a couple who are not big on the drinking scene, I really struggled to think of a hen event that would satisfy everyone. We stayed at the Pinfold for the weekend and I could not have had a better hen weekend. … see more
Little Thatch - Thatched Rutland 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 … see more

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