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

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180 Holiday homes

(38) 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
“Comfortable and Cosy Cottage in a lovely location” My wife and I stayed here for 4 nights on a cycling/walking visit to Rutland. The cottage was very clean and comfortable and superbly equipped with everything you could need plus nice touches such as wine, fruit, coffee tea and milk to get you started. The owner was very accommodating and helpful and was happy to squeeze us in at short notice. The cottage is located in a lovely village close by Rutland Water and was ideal for us as it was just a short hop on our bikes to view and enjoy this picturesque area. With the towns of Stamford and Oakham closeby it is in an ideal location to explore this delightful part of the country.

Certificate of Excellence

from £80 / night

£495 - £805 / week

Book View

Responds fast!
avg. 55 minutes

from £80 / night

(14) 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

from £75 / night

£350 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from £75 / night

(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 £110 / night

£625 - £795 / week

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Responds fast!
avg. 3 hours 24 minutes

from £110 / 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

£644 - £1,895 / week

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from £115 / night

(7) 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

£695 - £1,060 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from £125 / night

(4) Excellent 

15

Holiday barn rental

Rutland / Uffington

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly

from £150 / night

£750 / week

Book View

from £150 / night

(1) Excellent 

18

Holiday home rental

Rutland / Oakham

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly

from £100 / night

£700 / week

Book View

Responds fast!
avg. 1 hour 0 minutes

from £100 / 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

(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 £900 / night

£5,400 / week

Enquire View

from £900 / night

(13) 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

Book View

from £105 / night

(9) 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

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from £79 / night

(5) 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 £100 / night

£595 - £860 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from £100 / night

(1) Excellent 

21

Holiday home in Oakham

Rutland / Oakham

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary

from £120 / night

£840 - £980 / week

Book View

Responds fast!
avg. 40 minutes

from £120 / night

(32) 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

Certificate of Excellence

from £59 / night

£660 / week

Book View

Responds fast!
avg. 40 minutes

from £59 / night

(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 £140 / night

£495 - £900 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £140 / night

(1) Very Good 

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 

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

(23) Excellent 

22

Holiday cottage letting

Rutland / Oakham

2 4 min stay varies

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

from £99 / night

£520 - £930 / week

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from £99 / night

(17) 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
“Lovely accommodation to a get together for new year” This property is immaculate. We arrived to fresh bread,eggs and milk and not forgetting The home baked mince pies. The beds were comfortable the showers were powerful. Very spacious in all the rooms. The garden is a fabulous size unfortunately we didn't make much use of it due to it being December and there was snow there on our arrival. There is a shop over the road and a chip shop within walking distance. We went to the Sun inn for Sunday lunch.... beautiful home cooked quality food. The best roast I have had in a while and very reasonably priced. The village itself is lovely and quiet with beautiful properties to have a nosy around. Would defintley return here. Thank you Katie.

Certificate of Excellence

from £160 / night

£1,120 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from £160 / night

(9) Excellent 

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 - £1,120 / week

Book View

Responds fast!
avg. 2 hours 27 minutes

from £95 / night

(25) 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 £180 / night

£710 - £1,510 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £180 / 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

(12) 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 - £545 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from £85 / night

(28) 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 - £675 / week

Enquire View

from £90 / 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 37 minutes

from £65 / 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 9 minutes

from £78 / night

(13) Excellent 

28

Holiday apartment in Uppingham

Rutland / Uppingham

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Ask owner if suitable for children
  • Car not necessary

from £95 / night

£595 - £700 / week

Book View

Responds fast!
avg. 59 minutes

from £95 / 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

(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
“Brilliant get-away” Absolutely amazing time away from hectic city life. The property was formerly a railway station so it is quite special when you think of the history behind the layout of the house, e.g. the original station stairs and entrance doors. Well proportioned, with spacious living room featuring three 2/3 person sofas (two of which are double sofa beds), and modern TV & DVD player. The kitchen contains everything you could possibly need for your time away, including a microwave, and a breakfast table for 6. All three bedrooms (two are upstairs and the other is downstairs) are large doubles, all comfortably hosting double beds as well as fitted wardrobes, still with plenty of floor space to spare (we were able to easily place two travel cots in the master suite, and still have quite a lot of room to move around). There are two bathrooms: downstairs there is a wet room with power shower, and upstairs there is a bath tub and shower cubicle - both were practical and clean, with very high water pressure. The boiler was also very good, we had no problems with the water getting cold, especially in the mornings when everyone had a shower (and there were 8 of us). The owners live next door, and were incredibly friendly and accommodating. Overall I would definitely recommend this cottage to others who may be interested, and having been on many other cottage breaks - I can definitely say that this was by far one of the better ones we've been to, both in terms of facilities, picturesque location (with views of fields and sheep from every angle), and value for money.

Certificate of Excellence

from £100 / night

£475 - £700 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from £100 / night

(16) Excellent 

Certificate of Excellence

27

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 £107 / night

£550 - £998 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from £107 / 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 £70 / night

£450 / week

Book View

from £70 / night

(35) 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 £120 / night

£550 - £1,250 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from £120 / 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

from £125 / night

£415 - £495 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £125 / night

(16) 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 £95 / night

£450 - £560 / week

Book View

from £95 / 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

£565 - £730 / week

Book View

Responds fast!
avg. 3 hours 24 minutes

from £105 / 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

(44) Very Good 

24

Stamford holiday cottage rental

Rutland / Stamford

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden
“Relaxing” Having stayed at Two Chapel Lane with a friend in May, I would certainly make a return trip. The cottage itself is a very restful place with lovely, quality decor and very good facilities - I particularly liked the varied range of DVD's on offer and the real fire. It's proximity to Stamford and Burghley House was also very handy. Communication with the owner of the cottage was always friendly and helpful - I would thoroughly recommend staying at Two Chapel Lane and hope to do so again.

from £85 / night

£595 - £850 / week

Book View

Responds fast!
avg. 58 minutes

from £85 / 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 £99 / night

£520 - £1,000 / week

Book View

from £99 / night

(4) Excellent 

25

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 £85 / night

£380 - £530 / week

Book View

from £85 / 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

The Old Post Office
Excellent facilities, delightful and charming old cottage with all the mod cons to make you comfortable.

Sharon (Owner) has taken thought and care with the decor of her beautiful cottage to maintain its character and charm but also ensured it is clean and provides all the fascitiies to help you make the most of your stay. Lovely and well equipped kitchen. Having a dishwasher and washing machine is very helpful when you're away from home. Two of the bedrooms have a kingsize/double bed and the third a single bed and ideal for a child with books and it's cheerful decor. There are plenty of extras in the kitchen, not always provided in self catering, such as dishwasher tablets, washing up liquid, salt pepper, tea coffee, herbs, spices etc. I always take my own anyway when staying away as you cannot expect that all places will have so much available but it's worth sending Sharon an email to ask about anything you're not sure of to about bringing as she always replies promptly. Upstairs bathroom has a deep bath which was very comfortable it also has an overhead shower but we did not use that. Hambleton itself is lovely and quiet and very easy distance of Rutland Water which is great to cycle, walk or run round. The bed was much softer than we are used to but very comfortable and we slept well. Heating and hot water controls, easy to understand and use. Would recommend this to friends and family and happy to stay here again if we were visiting this area.see more
Postbox Cottage
Perfect cottage in pretty village

We loved our stay at Post Box cottage.Deceptively spacious and so well equipped even a good range of dvds and books and stairgates for our dog. The little private courtyard (and gorgeous weather!)meant we could eat outside most of the time. Perfect position to walk down to Rutland Water or 20 minutes by car to other places around the reservoir - all very pretty. A bit like the Cotswold and a less hilly Lake District. Easy roadside parking. We were sad to leave.see more
Waterend Barn
Just perfect!!

The house is wonderful, it was spotlessly clean, everything was provided. We really enjoyed every minute in this house. The village is pittoresque, the area is quiet, the landscape beautiful. Beds were very comfortable, two bathrooms available. Linen and towels provided very exceptionally clean and fresh. A perfect stay, we fully recommend this place.see more
GLASTON, stylish interior, open-plan living, en-suite master room, Ref 981550
Pleasantly surprised

We booked this last minute (couple of days before we planned to travel) and, with only a small selection of properties available in the area, figured we may have to accept a few concessions. Not so with this lodge. Set in a lovely quiet area just North of the main road traversing the Northern shore line of Rutland Water, the reservoir is a 15 walk from the site - great for a quick dog walk, or a few minutes by car. The lodge was extremely well equipped - a home from home - and very comfortable and clean. The photos on the website unfortunately make these lodges look s bit tired (in my opinion) and do not do them justice. Made with ecology in mind, they are very warm and well insulated. Being a lovely summer, the log burner was not required but with this lit, in winter, this would create a lovely cozy atmosphere in the lodge after dark. Rutland Water and neighbouring villages have a lot to offer walkers, cyclists and nature lovers - Ospreys were in the area as we visited. The lodge takes dogs which is a bonus. Thankfully, the hotel also allows dogs in its bar/restaurant and this theme is common throughout the area with many pubs and restaurants also welcoming people with their 4 legged friends. We will most definitely be back to this lovely place.see more
The Gallery Apartment, Oakham, Rutland
In Town

The Gallery was clean and well maintained. The location is ideal for exploring Oakham requiring only a short walk to visit the town centre, shops and the castle etc.The WiFi worked very well and the TV offered a wide variety of programmes. … see more
Near Rutland Water. A Pet Friendly 18th Century Cottage with a historical Past.
Everything you could need from a perfect dog friendly cottage

Primrose Hall cottage, is a cosy comfortable home from home historic holiday accommodation. Ideal for a short or long holiday break, with everything could possibly need, to totally rest and relax. The owners have gone of their way to make sure it’s well equipped.They have thought of everything. That include Comfortable beds, good heating if needed,plenty of towels,books,games a welcoming delicious bowl of fruit, bottles of milk and wine. Our dog was spoilt too by the dog biscuits left for her. With bowls and towels for her if needed.The pretty village has a little well stocked shop and dog friendly pub all within walking distance. And others not too far away. There are plenty of lovely walks in the beautiful surrounding area. We especially fell in love with the Rutland Lakes. So much to do if you enjoy watersports, bike rides or just amazing scenery and walks around the waters. We would definitely like to stay again and have already talked our friends into making a future booking.see more