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

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Rutland

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150 Holiday homes

(4) Excellent 

20

Greetham holiday cottage rental

Rutland / Greetham

2 6 Min stay varies

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

from £125 / night

£795 - £1,205 / week

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Responds fast!
avg. 3 hours 19 minutes

from £125 / night

(16) 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
“nice cottage, helpful owner” Mouse Cottage is well positioned close to Oakham and is well equipped and should be comfortable. I say 'should be' because, unfortunately, the heating and hot water packed up during our stay and it was freezing! fortunatel
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from £95 / night

£250 - £500 / week

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Responds fast!
avg. 51 minutes

from £95 / night

(28) Excellent 

Certificate of Excellence

28

Holiday cottage in Hambleton

Rutland / Hambleton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
“Wonderful!” A beautiful cottage in a stunning location Well equipped, clean and comfortable. Loved the little extras like bread from the local bakery. We will back!
…see more

Certificate of Excellence

from £110 / night

£550 - £1,250 / week

Book View

Responds fast!
avg. 38 minutes

from £110 / 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

(3) 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 £111 / night

£625 - £1,521 / week

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from £111 / night

(13) Very Good 

14

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
“Great place to stay while discovering Rutland/Oakham area.” This self-catering accommodation was well-appointed and spacious. The views from all rooms were pleasant and we loved watching the birds at their feeder while having breakfast. We were able
…see more

from £100 / night

£400 - £560 / week

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from £100 / night

(8) Excellent 

13

Apartment rental in Oakham

Rutland / Oakham

2 4 Min stay varies

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

from £85 / night

£535 - £575 / week

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from £85 / 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
“Perfect cosy cottage stay” The photographs of this property are fantastic and don't even do it justice- this is one of those rare occasions where it is better in real life! The cottage is gorgeous, really beautifully and thoughtfully decorated in a
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from £85 / night

£595 - £850 / week

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Responds fast!
avg. 1 hour 24 minutes

from £85 / 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

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from £140 / night

(11) Excellent 

14

Holiday cottage in Market Overton

Rutland / Market Overton

3 5 Min stay varies

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

from £115 / night

£715 - £765 / week

Enquire View

from £115 / night

(11) Very Good 

Certificate of Excellence

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
“Just what we were looking for” We needed somewhere to stay while I attended my best friends wedding and where we were in easy access to Rutland Water, which we explored for the rest of the weekend. This place was perfect, with two dogs (one of which l
…see more

Certificate of Excellence

from £140 / night

£495 - £900 / week

Book View

Responds fast!
avg. 38 minutes

from £140 / 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. 2 hours 3 minutes

from £78 / night

(1) Excellent 

27

Holiday barn in Greetham

Rutland / Greetham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £220 / night

£1,250 - £2,020 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £220 / night

(3) Excellent 

7

Holiday apartment in Greetham

Rutland / Greetham

1 4 Min stay varies

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

from £95 / night

£595 - £1,060 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £95 / 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
“Traditional thatched cottage” Lovely little cottage with great extra little touches. Probably not ideal for less mobile people. Good communications with regards to booking and arrival etc. Lovely having all extra white goods aswell.
…see more

from £125 / night

£415 - £475 / week

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Responds fast!
avg. 38 minutes

from £125 / night

(20) Excellent 

30

Uppingham holiday home rental

Rutland / Uppingham

5 14 2 nights min

  • 5 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
“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 brilli
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from £900 / night

£5,400 / week

Enquire View

from £900 / night

(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

from £117 / night

£620 - £1,050 / week

Enquire View

from £117 / night

(13) Excellent 

Certificate of Excellence

12

Holiday guest house in Hambleton

Rutland / Hambleton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
“Perfect place in a perfect setting” Absolutely loved everything about this annex. Amazing location with everything on your doorstep but at the same time peace and quiet. Will definitely go back.
…see more

Certificate of Excellence

from £75 / night

£350 / week

Book View

Responds fast!
avg. 38 minutes

from £75 / 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 £105 / night

£495 - £785 / week

Book View

Responds fast!
avg. 3 hours 18 minutes

from £105 / 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
“Beautiful little cottage” My friend and I stayed for 2 nights at Pibbles Nook and loved it. Alison and Ken (lovely people) put so much effort into making everything perfect for our stay. The cottage was spotlessly clean and there was a lovely welcom
…see more

Certificate of Excellence

from £95 / night

£665 - £1,050 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £95 / 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

(30) 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
“Brilliant location, facinating convertion deserving higher spec on details” Excellent location with well presented outside areas. Station conversion is fascinating but we were disappointed with some details. There were 3 light bulbs out, and we couldn
…see more

Certificate of Excellence

from £100 / night

£475 - £700 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from £100 / night

(11) 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
“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,
…see more

Certificate of Excellence

from £155 / night

£1,085 / week

Book View

Responds fast!
avg. 38 minutes

from £155 / night

(3) Very Good 

19

Holiday home in Oakham

Rutland / Oakham

3 9 2 nights min

  • 3 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £400 / night

£2,500 / week

Book View

from £400 / night

(2) Excellent 

12

Barn rental in Whitwell

Rutland / Whitwell

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly

from £65 / night

£455 / week

Book View

Responds fast!
avg. 3 hours 47 minutes

from £65 / night

12

Log cabin rental in Oakham

Rutland / Oakham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation

from £117 / night

£620 - £1,050 / week

Enquire View

from £117 / night

(2) Excellent 

18

Holiday apartment in Manton

Oakham / Manton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
“Peace and quiet and a fantastic view” A beautiful apartment that has everything you could want, including a terrific welcome pack of scrumptious goodies. Quite secluded, it is very peaceful and has the most wonderful view over Rutland Water. The own
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from £75 / night

£450 - £625 / week

Book View

from £75 / night

(28) Excellent 

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
“Beautiful holiday home!” We found this accommodation only a few days before our trip and the owner couldn't have been more accommodating! Everything was arranged in a couple of emails and absolutely no fuss! It's amazing how this property has been
…see more

from £68 / night

£485 - £755 / week

Book View

Responds fast!
avg. 2 hours 22 minutes

from £68 / 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
“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

from £120 / night

£610 - £745 / week

Book View

Responds fast!
avg. 3 hours 18 minutes

from £120 / night

(7) 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

(4) Excellent 

15

Holiday apartment in Uppingham

Rutland / Uppingham

2 4 1 night min

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

from £90 / night

£490 - £560 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £90 / night

(21) Very Good 

Certificate of Excellence

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
“Lovely house, wonderful area.” With five bedrooms and three bathrooms, this property was ideal for us to stay with our daughter and her family, and our two dogs, giving us all plenty of space to spread out. We had some lovely walks close by and Rutla
…see more

Certificate of Excellence

from £165 / night

£695 - £1,160 / week

Book View

Responds fast!
avg. 38 minutes

from £165 / night

(1) Excellent 

11

Holiday apartment in Manton

Oakham / Manton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • 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

(24) 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

£475 - £625 / week

Enquire View

from £90 / night

(26) Excellent 

Certificate of Excellence

37

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
“A very peaceful and relaxing location.” The Chapel was an ideal place to stay for a few days. Ideal location for Rutland Water and other amenities in the area.
…see more

Certificate of Excellence

from £57 / night

£660 / week

Book View

Responds fast!
avg. 23 minutes

from £57 / 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
“Perfect weekend away for four grown ups and a toddler!” We stayed at the cottage for a university reunion; four thirty something ladies and one toddler! The cottage was just as described and had every amenity that we could have asked for. The accommod
…see more

from £85 / night

£595 / week

Enquire View

from £85 / night

(13) 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
“Xmas stay” Wonderful time, cottage beautifully clean, homely and everything we needed. Beds really good quality, beautifully decorated, coordinated bedrooms. Open fire was the icing on the cake. Jennifer the owner is a lovely lady, nothing to much tro
…see more

Certificate of Excellence

from £110 / night

£700 - £820 / week

Book View

Responds fast!
avg. 1 hour 58 minutes

from £110 / night

(12) 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

from £95 / night

£595 - £900 / week

Book View

Responds fast!
avg. 2 hours 6 minutes

from £95 / night

(17) Excellent 

24

Holiday cottage in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Private garden
“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 l
…see more

from £99 / night

£520 - £1,000 / week

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from £99 / 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

Osprey View
Stunning views, lovely property and friendly welcome from owner plus Gabby the dog!

Lovely location with a chance to catch a glimpse of an Osprey. Gorgeous decking area to sit and watch the sun go down with a glass of wine and if you are lucky, then Gabby the dog might come and sit with you too! Generous welcome pack supplied including locally made bread, milk, tea, coffee, fruit, jam and orange juice. Made to feel very welcome by the owner who has furnished the property to an excellent standard and I would not hesitate to stay again.see more
Near Rutland Water. A Pet Friendly 18th Century Cottage with a historical Past.
Every possible need catered for!

Our stay at Primrose Hall, Empingham has been wonderful...Catherine made us feel welcome and at home...the walks are so accessible...the cottage had everything we could wish for...and dog friendly too! We'll definitely be back! … see more
Moo Cow Cottage- self catering
Excellent

A lovely cottage in a great location thoroughly recommend we were three generations of a family plus the dogs and it suited us all. Jennifer the owner was very friendly and helpful and she had baked us a delicious chocolate cake. We'll visit again. , … see more
The Gallery Apartment, Oakham, Rutland
Wonderful stay

Appartment arranged and furnished with great care and taste, went that extra little dstanice to make it really comfortable.Very near to Rutland Water, fabulous bird watching despite weather … see more
Manor View Cottage
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.see more
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 furniture and all mod cons was perfect. We had everything we needed for a really comfortable stay - from kitchen equipment to a large tv and great sound system. The house had the perfect level of luxury - warm spacious bedrooms, comfortable beds, lots of towels and also some gift tolietries. We felt very pampered and well looked after, but above all we just felt really at home. I wholeheartedly recommend the Corner House - one of the best holiday houses we've stayed in. Also very friendly and helpful email correspondence with the owner and housekeeper.see more