Cottages in Rutland and Self catering accommodation - Holiday Lettings - Holiday Rentals Rutland

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Rutland

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172 Holiday homes

8

Holiday shepherds hut in Uppingham

Rutland / Uppingham

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly

from £45 / night

£230 / week

Book View

from £45 / night

(13) Excellent 

12

Holiday guest house in Hambleton

Rutland / Hambleton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
“A lovely stay” Beautiful little place, a home from home. The view from the balcony was stunning. A lovely surprise was the date loaf that awaited us. Perfect for a relaxing break away

from £75 / night

£350 / week

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Responds fast!
avg. 2 hours 30 minutes

from £75 / night

(30) Excellent 

28

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
“a perfect house” 6 of us stayed here for 5 days - perfect location, great house, comfy beds and space to spread out in.

from £120 / night

£550 - £1,250 / week

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Responds fast!
avg. 2 hours 30 minutes

from £120 / night

(22) 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
“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. Huge garden for games and bbq, spacious clean bedrooms for everyone to get a decent kip. The cinema room, hot tub, sauna and pool mean that there is something for everyone and people can relax and chill whilst those more into drinking and acting silly can use the massive kitchen/dining space to crack on and have a good time. All this and price paid per person was cheaper than what the stags paid to go out just down the local pubs. Katie also helps you organise extra activities if you want. We chose to have a visiting spa therapist on the Sunday and everyone chilled and had a day of pampering - just what a stressed bride to be needs. This venue literally caters for any type of bride/hens and the immaculate house with every modern day facility required will not disappoint.

from £900 / night

£5,400 / week

Enquire View

from £900 / night

(32) Excellent 

Certificate of Excellence

21

Cottage accommodation in Empingham

Rutland / Empingham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Privliged to say we have stayed at Primrose Hall AMAZING.” Catherine & Simon made us so welcome especially Cracker our rescue dog. This village hall conversion is stunning Catherine & Simon must feel very proud, so comfortable cosy and short of nothing. A very welcome bottle of wine also the special touches fresh fruit and flowers and choccies pure heaven thats all I can say and many thanks for a great stay. We also found all the information about the surrounding area very useful.

Certificate of Excellence

from £68 / night

£485 - £755 / week

Book View

Responds fast!
avg. 1 hour 5 minutes

from £68 / night

(4) Excellent 

13

Holiday lodge in Exton

Rutland / Exton

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly

from £115 / night

£625 - £1,521 / week

Book View

from £115 / night

(24) Excellent 

Certificate of Excellence

7

Stretton holiday cottage rental

Rutland / Stretton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Private garden

Certificate of Excellence

from £60 / night

£380 - £800 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from £60 / night

(13) 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
“Cosy home in pretty village” Dicks Cottage is a delightful thatched cottage in a pretty village. It's extremely well equipped and very warm and cosy. We had everything we needed. Kitchen is well equipped and the beds are very comfortable. We had a very enjoyable stay and will certainly be back.

Certificate of Excellence

from £160 / night

£1,120 / week

Book View

Responds fast!
avg. 38 minutes

from £160 / night

(7) Very Good 

Certificate of Excellence

11

Holiday cottage in Empingham

Rutland / Empingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden

Certificate of Excellence

from £95 / night

£665 - £1,050 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from £95 / night

(8) Very Good 

27

Holiday lodge with golf nearby in Greetham

Rutland / Greetham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 km
  • Child friendly
  • Pet friendly

from £79 / night

£375 - £835 / week

Book View

from £79 / night

(12) Excellent 

18

Holiday cottage in Market Overton

Rutland / Market Overton

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

from £105 / night

£715 - £765 / week

Enquire View

from £105 / 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 £100 / night

£490 - £560 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £100 / night

(7) Very Good 

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 £120 / night

£635 - £745 / week

Book View

from £120 / night

(6) Excellent 

Certificate of Excellence

20

Greetham holiday cottage rental

Rutland / Greetham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £125 / night

£825 - £1,205 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from £125 / night

(23) Very Good 

23

Holiday home accommodation

Rutland / Cottesmore

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly

from £165 / night

£695 - £1,160 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £165 / night

(17) Excellent 

18

Cottage rental in Braunston-in-Rutland

Rutland / Braunston-in-Rutland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly
“Dream Cottage in Delightful Village” This is an excellent cottage.It is very comfortable and clean with two good bedrooms and a downstairs bath/shower room.There is a suntrap garden just right for a bbq.Ample information is given about the large number of places to visit in the area.Rutland water is nearby with its wide range of outdoor activities including ,walking,cycling,birdwatching.The village has two very good pubs with real ale and tasty food.The area has a variety of interesting pubs and restaurants. It is a very good place for a romantic break or an outdoor activity holiday. We were reluctant to leave and look forward to our next visit.

from £95 / night

£350 - £500 / week

Book View

Responds fast!
avg. 51 minutes

from £95 / night

(15) Very Good 

Certificate of Excellence

24

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 £100 / night

£400 - £560 / week

Book View

from £100 / night

(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
“Unusual Building - Comfortable Stay” Our family really enjoyed our 2 night stay in the converted railway station which was comfortably equipped, sleeping 7 very easily. Surrounding villages very pretty, with welcoming pubs - dinner in Coach House at South Luffenham was excellent. Rutland Water close by and beautiful, also Stamford was a very interesting town to visit.

Certificate of Excellence

from £100 / night

£475 - £700 / week

Book View

from £100 / night

(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
“Lovely idealistic quiet cottage” We stayed for a week at the cottage, there was 4 people and we found it a little small for that number of adults, but we were warned, but they did everything they could to help us out and the cottage was ideal, cosy, warm, clean and very querky and old. WIFI was very good but poor mobile signal in cottage. The garden is good for a dog as it is enclosed and private, with a table and bench set. Would not hesitate to return or to recommend it to others.

from £125 / night

£415 - £475 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £125 / night

(4) Excellent 

Certificate of Excellence

7

Holiday apartment in Greetham

Rutland / Greetham

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £95 / night

£595 - £1,060 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from £95 / night

(4) Excellent 

15

Holiday barn rental

Rutland / Uffington

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly

from £140 / night

£650 / week

Book View

from £140 / night

(12) Excellent 

23

Holiday cottage in Belton-in-Rutland

Rutland / Belton-in-Rutland

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 160 km
  • Child friendly
  • Pet friendly

from £85 / night

£595 / week

Enquire View

from £85 / night

(15) Excellent 

Certificate of Excellence

23

Holiday home in Stretton

Rutland / Stretton

3 6 3 nights min

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

Certificate of Excellence

from £100 / night

£500 - £820 / week

Book View

Responds fast!
avg. 1 hour 29 minutes

from £100 / night

(2) Excellent 

8

Oakham holiday apartment rental

Rutland / Oakham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly

from £60 / night

£290 / week

Book View

from £60 / night

(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 £78 / night

£560 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from £78 / night

(42) Very Good 

24

Stamford holiday cottage rental

Rutland / Stamford

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Cosy, warm and well equipped” Overall very comfortable stay and owners went to great lengths to accommodate our needs. Parking was easy. Only minor issues were that better operating instructions for TV, oven and microwave would have made it a bit easier but nothing to stop us going back again.

from £85 / night

£595 - £850 / week

Book View

Responds fast!
avg. 1 hour 15 minutes

from £85 / night

(2) Excellent 

18

Holiday apartment in Manton

Oakham / Manton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

from £75 / night

£450 - £625 / week

Book View

from £75 / night

(3) Very Good 

12

Barn rental in Whitwell

Rutland / Whitwell

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly

from £65 / night

£455 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £65 / 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 £115 / night

£560 - £785 / week

Book View

from £115 / night

(13) Excellent 

31

Holiday apartment in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask owner if suitable for children
  • Car not necessary

from £95 / night

£595 - £900 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from £95 / night

(10) Excellent 

Certificate of Excellence

13

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 £85 / night

£535 - £575 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from £85 / night

(11) 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
“perfect retreat!!” What a fantastic property. The accommodation was excellent with plenty of room to spread out. The local pub provided a great evening meal on Saturday (we also had lunch there as well). Local to Rutlands towns and the water. Could not fault this at all. Mel was on hand if we had any problems - which we did not to be honest.

from £140 / night

£495 - £900 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £140 / night

(25) Excellent 

24

Edith Weston holiday cottage rental

Rutland / Edith Weston

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 km
  • Suitable for children age 5+
  • Pet friendly

from £90 / night

£500 - £625 / week

Enquire View

from £90 / night

(17) Excellent 

29

Holiday cottage in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Private garden

from £99 / night

£520 - £1,000 / week

Book View

from £99 / night

(29) Excellent 

Certificate of Excellence

36

Holiday converted chapel in Wing

Oakham / Wing

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
“The Chapel Wing” We had a very good stay The Chapel was a very interesting and well equipped base to stay and explore the area. The owners were helpful when we had a problem and were able to give any advise we needed. With several folders on the amenities in the area which were very useful.

Certificate of Excellence

from £59 / night

£660 / week

Book View

Responds fast!
avg. 17 minutes

from £59 / night

(1) Excellent 

12

Holiday log cabin in Oakham

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £81 / night

£445 - £900 / week

Enquire View

from £81 / night

(20) Excellent 

28

Oakham holiday cottage rental

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 115 km
  • Ask owner if suitable for children
  • Private garden

from £99 / night

£520 - £930 / week

Book View

from £99 / night

42

Holiday yurt rental

Rutland / Greetham

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

from £126 / night

£882 / week

Book View

from £126 / night

(2) Excellent 

11

Holiday apartment in Manton

Oakham / Manton

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

from £100 / night

£380 - £530 / week

Book View

from £100 / night

12

Holiday log cabin letting

Rutland / Oakham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from £117 / night

£595 - £1,010 / week

Enquire View

from £117 / night

Why Rutland?

The smallest county in England, this East Midlands delight is predominantly rural, and therefore incredibly scenic. With the enormous Rutland Water lake in the centre of the county, and plenty of activities on offer, isn’t it time you booked your next holiday rental in Rutland?

About Rutland

But there's lots of excitement to be had, both on and off the lake, and some incredible routes for walking, cycling, or just generally exploring.

What to Do

Uncover local history at the Rutland County Museum, and get a feel for what it would be like to live in such a rural area. Oakham Castle is a charming place to look around, with an unusual horseshoe collection that's well worth checking out.

Get out on the lake. Whether you prefer sailing or fishing, it's a beautiful place to spend some time. Or head for Aqua Park Rutland, an adrenaline-packed inflatable obstacle experience on the water that the adventurous will love.

Top Rutland Travel Tips

To enjoy some of the best of the rural English countryside, be sure to book your next holiday rental in Rutland today.

Top Destination reviews

Self Catering Holiday Cottage
Beautiful well equipped cottage.

Group of 7 Uni friends stayed for the weekend. We've been doing yearly get together for 10 years and this is the most comfortable and best equipped cottage we've stayed at. Knives that actually cut, measuring scales, enough pots and pans etc plenty of children's eating stuff too (left the kids at home so didn't try it). We didn't run out of toilet roll either! Owners were lovely, available to show us round and came straight over when we had an issue with the fire alarm. Location is lovely, we went for a nice walk round Rutland water. Thoroughly enjoyed our stay!see more
Garden Apartment, Manton Lodge
Amazing dog friendly farm style apartment!

Home away from home. Stylish, à la cottage apartment with stunning views and amazing location for long walks just moments from Ruthland Water. Very pleasnat and helpful owner. This farm with animals around would be great fun for kids too. We enjoyed our stay and exploring the area. Very peaceful place to recharge your batteries. Extremely comfortable bed and cute bird feeder outside our window are our favourites! Thank you Carolinesee 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
Postbox Cottage
We don't want to leave

The final night of our stay at post box cottage. This 2 bedroom, 2 bathroom cottage has suited us 4 lady cyclists simply perfectly with secure storage for our bikes and easy access to Rutland water and the surrounding countryside. The cottage itself is spotlessly clean, cosy and warm with plenty of instant hot water. A very well equipped kitchen also has a few basic ingredients should you wish to cook. If you don't, there are many good watering holes close by. Thank you, we will be back.see more
Daphne's Cottage
Bank Holiday

Lovely clean cottage within easy reach of beautiful countryside. Very helpful landlady and very reasonably priced. … see more
Barrowden and Wakerley Station
Holiday home

Really lovely big house with a superb staircase, 2 patios that we used to follow the sun and a reasonable garden … see more