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

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Rutland

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161 Holiday homes

(21) 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
“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 cou
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from £900 / night

£5,400 / week

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from £900 / 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

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from £79 / night

(9) 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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Responds fast!
avg. 3 hours 42 minutes

from £85 / night

(5) Excellent 

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

from £125 / night

£825 - £1,205 / week

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Responds fast!
avg. 2 hours 57 minutes

from £125 / night

(15) 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
“Peaceful & Convenient” We were in the Valley Apartment - comfortable with lovely views and ideal for a week's stay in order to catch up with nearby family. Being close to Rutland Water was another advantage as was the choice of many good pubs in the
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from £100 / night

£400 - £560 / week

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from £100 / 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

£500 - £625 / week

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from £90 / night

(12) 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
“Wow, stunningly beautiful traditional cottage” Wow, stunningly beautiful traditional cottage, perfectly restored and maintained to very high standards. Very comfortable, fully functional for our family of ten holiday for four days. Very well equipped
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Certificate of Excellence

from £155 / night

£1,085 / week

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Responds fast!
avg. 55 minutes

from £155 / night

(23) Excellent 

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

from £60 / night

£380 - £800 / week

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Responds fast!
avg. 3 hours 16 minutes

from £60 / night

(29) 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
“a perfect house” 6 of us stayed here for 5 days - perfect location, great house, comfy beds and space to spread out in.
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Certificate of Excellence

from £120 / night

£550 - £1,250 / week

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Responds fast!
avg. 2 hours 37 minutes

from £120 / night

(31) 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
“Great stay” Terrific house plenty of room clean tidy warm our second stay definitely be back Love the little bits of history
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Certificate of Excellence

from £100 / night

£475 - £700 / week

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Responds fast!
avg. 3 hours 53 minutes

from £100 / 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

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from £115 / 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

(4) 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

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Responds fast!
avg. 3 hours 37 minutes

from £100 / night

(12) Excellent 

15

Holiday cottage in Market Overton

Rutland / Market Overton

3 5 Min stay varies

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

from £105 / night

£715 - £765 / week

Enquire View

from £105 / 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
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Certificate of Excellence

from £165 / night

£695 - £1,160 / week

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Responds fast!
avg. 58 minutes

from £165 / night

(3) Excellent 

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

from £95 / night

£595 - £1,060 / week

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Responds fast!
avg. 2 hours 57 minutes

from £95 / 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
“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
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from £120 / night

£635 - £745 / week

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from £120 / 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
“Mr” We had a lovely weekend in this beautiful cottage! The attention to detail both for decoration and furniture makes this cottage stand out from the rest. We will definitely be back! Big thank you to Alison and Kenneth.
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Certificate of Excellence

from £95 / night

£665 - £1,050 / week

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Responds fast!
avg. 1 hour 50 minutes

from £95 / 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
“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 no
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Certificate of Excellence

from £140 / night

£495 - £900 / week

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Responds fast!
avg. 58 minutes

from £140 / night

(14) 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 £115 / night

£700 - £820 / week

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Responds fast!
avg. 1 hour 56 minutes

from £115 / 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
“Mr” It was a lovely cottage clean and tidy lovely inclosed garden for the dog the kitchen was lovely had every we wanted
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from £125 / night

£415 - £475 / week

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Responds fast!
avg. 58 minutes

from £125 / 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
“Our weekend break at Waterend Barn was everything we hoped it would be.” I stayed with my daughter, her 3 children ages 6,7,14 and my niece (24) for three nights. We all thoroughly enjoyed all the home comforts of the cottage. The children especiall
…see more

from £85 / night

£595 / 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 8 minutes

from £85 / 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

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Responds fast!
avg. 1 hour 50 minutes

from £78 / 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
“Clean, friendly, wonderful views, perfect place to stay.” What a wonderful place to stay. The owner was there to greet us with a friendly welcome. Beautiful fresh locally baked bread, butter, milk, biscuits etc. were all left out for our arrival, a ve
…see more

Certificate of Excellence

from £75 / night

£350 / week

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Responds fast!
avg. 2 hours 20 minutes

from £75 / night

(30) 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
“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 nothin
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from £68 / night

£485 - £755 / week

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Responds fast!
avg. 1 hour 14 minutes

from £68 / night

(2) Excellent 

18

Holiday apartment in Manton

Oakham / Manton

1 2 2 nights min

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

from £75 / night

£450 - £625 / week

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from £75 / 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

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Responds fast!
avg. 2 hours 6 minutes

from £95 / 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

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from £117 / 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

(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

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from £115 / night

(27) 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
“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 amen
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Certificate of Excellence

from £57 / night

£660 / week

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Responds fast!
avg. 14 minutes

from £57 / 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
“What a lovely cottage in a great village in a fantastic area.” Our recent stay at Mouse cottage was a joy. The cottage is equiped with everything you need for a break in the quiet countryside. Rutland water is a must to visit and is not far from the c
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from £95 / night

£350 - £500 / week

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Responds fast!
avg. 51 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

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from £60 / night

(19) Excellent 

23

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

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from £99 / night

(2) 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

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from £100 / night

(2) Excellent 

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

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Responds fast!
avg. 3 hours 47 minutes

from £65 / night

(17) Excellent 

24

Holiday cottage in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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
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from £99 / night

£520 - £1,000 / week

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from £99 / night

(21) Excellent 

14

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

4

Lodge rental in Whitwell with golf nearby

Rutland / Whitwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

Pricing unknown

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Pricing unknown

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

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
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 trouble. … 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
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
Barrowden and Wakerley Station
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't find a bread knife or oven glove. There were no tea towels or dishwasher tablets and the downstairs bedroom would have benefited from a dressing table, mirror and perhaps a second bedside table and light. The property was clean and spacious with comfortable beds and was so good in most respects we felt it was a shame to spoil it with small details. It deserved a higher spec. We would certainly consider going againsee more
Garden Room Apartment, Manton Lodge Farm
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