50 Best Vacation Rentals in Rutland - Holiday Lettings - Cabins

Close

View larger map

Also consider

Oakham
24 properties
Uppingham
9 properties

Rutland

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

172 Vacation rentals

(13) Excellent 

12

Vacation guest house in Hambleton

Rutland / Hambleton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
This is the guest house to the main house. There are views of Rutland Water from both bedrooms. There is no kitchen or separate livingroom. . There is a small fridge, microwave, toaster and tea and coffee making facilities. The property is upstairs and has a wrap around …see more

from $99 / night

$462 / week

Book View

Responds fast!
avg. 2 hours 30 minutes

from $99 / night

(30) Excellent 

28

Vacation cottage in Hambleton

Rutland / Hambleton

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
The Old Telegraph and Post Office cottage is in the village of Hambleton on a peninsula in the middle of Rutland Water, one of Europe's largest reservoirs. Hambleton is probably one of the nicest village locations in England. There are 3 reception rooms and a kitchen a …see more

from $159 / night

$726 - $1,650 / week

Book View

Responds fast!
avg. 2 hours 30 minutes

from $159 / 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 mi
  • Child friendly
Mouse Cottage (no we don't know why it is called Mouse Cottage, it always has been according to locals) is a stone and brick built cottage which sits opposite the village green in the beautiful village of Braunston-in-Rutland. The cottage has oil fired central heating, …see more

from $126 / night

$462 - $660 / week

Book View

Responds fast!
avg. 51 minutes

from $126 / night

8

Vacation shepherds hut in Uppingham

Rutland / Uppingham

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
The tiny home offers a new way to stay. This trendy, compact and modern space makes the perfect stay for anyone visiting our beautiful county of Rutland. Uppingham is a picturesque market town situated in the heart of Rutland and only a short drive to the fabulous rese …see more

from $60 / night

$304 / week

Book View

from $60 / night

(12) Excellent 

18

Vacation cottage in Market Overton

Rutland / Market Overton

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden
The Green is a self-catering Rutland holiday cottage with a pretty private rear garden in the rural conservation village of Market Overton just a stone’s throw away from Rutland Water. Rutland is excellent for walking and cycling and The Green holiday cottage provides …see more

from $139 / night

$944 - $1,010 / week

Inquire View

from $139 / night

(13) Excellent 

Certificate of Excellence

17

Vacation cottage in Cottesmore

Rutland / Cottesmore

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Dick's Cottage is situated in the heart of Rutland in the village of Cottesmore which is near the market towns of Stamford, Oakham, Uppingham & only 5 miles from Rutland Water. A beautiful thatched grade two listed building, awards a 4 * Gold rating by Visit England, s …see more

Certificate of Excellence

from $212 / night

$1,479 / week

Book View

Responds fast!
avg. 38 minutes

from $212 / night

(22) Excellent 

31

Uppingham Vacation home rental

Rutland / Uppingham

5 14 2 nights min

  • 5 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
This house has been newly renovated and available for short break lets, weekend stays, group get together soon due to its fabulous entertaining space. The stunning open plan kitchen had dining are for 14 and breakfast bar. Fully equipped kitchen with all modern amen …see more

from $1,188 / night

$7,129 / week

Inquire View

from $1,188 / night

(8) Very Good 

27

Vacation lodge with golf nearby in Greetham

Rutland / Greetham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Child friendly
  • Pet friendly
Our luxury eco-friendly 4* Lodge is one of several set amidst 276 acres of rolling Rutland countryside, just a few minutes drive from Rutland Water. The Lodges are a perfect base for golfing, sailing, windsurfing, birdwatching, cycling, walking – or why not just sit bac …see more

from $105 / night

$495 - $1,103 / week

Book View

from $105 / 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
The larger of our two barns has a luxurious and cosy feel with underfloor heating throughout and a log burner for wintry nights. A double room (king sized bed) with a stunning view over our garden and small flowing pond. You also have a private lawned area to sit outsid …see more

from $86 / night

$601 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from $86 / night

(11) Very Good 

8

North Luffenham Vacation home rental

Rutland / North Luffenham

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 5 mi
  • Child friendly
  • Pet friendly
Newly redecorated and reburbished, this beautiful period cottage set in the pretty village of North Luffenham can sleep up to 7 persons. North Luffenham is an attractive village and is a great central spot for viewing all that Rutland has to offer. Manor View Cot …see more

from $185 / night

$654 - $1,188 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $185 / night

(6) Excellent 

Certificate of Excellence

20

Greetham Vacation cottage rental

Rutland / Greetham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Halliday's Folly, named as such by locals a hundred and fifty years ago, is a unique and historic building built in 1850 by Thomas Charity Halliday, a stonemason and corn merchant. Thomas Halliday restored and repaired churches all over the country and was in the habit …see more

Certificate of Excellence

from $165 / night

$1,089 - $1,591 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from $165 / night

(4) Excellent 

Certificate of Excellence

7

Vacation apartment in Greetham

Rutland / Greetham

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Studio Apartment: This is a very comfortable and spacious studio apartment with fully fitted kitchen, bedroom area, living room with sofa bed and shower room. Guests will not feel cramped at all and will enjoy the original features that have been retained whilst also …see more

Certificate of Excellence

from $126 / night

$786 - $1,400 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from $126 / night

(33) Excellent 

Certificate of Excellence

18

Vacation cottage in Wakerley

Rutland / Wakerley

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
An admirable location situated between two rural villages Barrowden and Wakerley which overlook the River Welland, short walk to the nearest pub known for their home ales and good quality food. Provides affordable indulgence for holidaymakers seeking to relax and expl …see more

Certificate of Excellence

from $132 / night

$627 - $924 / week

Book View

from $132 / night

(29) Excellent 

Certificate of Excellence

36

Vacation converted chapel in Wing

Oakham / Wing

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
ABOUT THE CHAPEL: The Chapel, Wing is an early 19th Century stone built Grade II listed Methodist Chapel sympathetically converted at the turn of the 21st Century to create a unique Modernist open plan house. Winner of The George Phillips Award and featured in "Living E …see more

Certificate of Excellence

from $78 / night

$872 / week

Book View

Responds fast!
avg. 17 minutes

from $78 / night

(15) Very Good 

Certificate of Excellence

24

Vacation 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
Manton Lodge Farm is a stunningly-positioned 18th-century stone farmhouse set in more than 100-acres of rolling grassland in rural Rutland. It boasts far-reaching views across the sweeping River Chater valley, and is a short distance from Rutland Water. We offer two m …see more

Certificate of Excellence

from $132 / night

$528 - $740 / week

Book View

from $132 / night

(14) Very Good 

8

Vacation cottage rental

Rutland / Wakerley

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The property has one double bedroom but with a double sofa bed in the lounge, can accommodate 2/4 people and makes a fantastic romantic hideaway, a relaxing countryside break or work bolt hole. Fully equipped kitchen including: Cooker and Hob, Dishwasher, Fridge/free …see more

from $165 / night

$548 - $627 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $165 / night

(4) Excellent 

15

Vacation barn rental

Rutland / Uffington

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
Situated in the idyllic village of Uffington just outside the historic town of Stamford 'The Barn' is an immaculately presented, self catering spacious two bedroom en-suite conversion. With a tennis court and large gardens, this family run accommodation is perfect fo …see more

from $186 / night

$862 / week

Book View

from $186 / 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
A two bedroom self catering apartment situated in the centre of the historic market town of Oakham. The building was converted to an apartment in 2015 and provides accommodation on the first floor with two bedrooms accommodating four guests, a sitting room with dining …see more

Certificate of Excellence

from $113 / night

$707 - $759 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from $113 / night

(2) Excellent 

8

Oakham Vacation apartment rental

Rutland / Oakham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
The Stables Flat is attached to our secluded farmhouse. We are surrounded by rolling fields grazed by cattle, sheep and horses. We keep pigs, ducks and hens. The house is down a quiet country lane without passing cars, apart from farm traffic. The light, airy flat has …see more

from $80 / night

$383 / week

Book View

from $80 / night

(7) Very Good 

Certificate of Excellence

11

Vacation cottage in Empingham

Rutland / Empingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Pibbles Nook is exquisitely furnished, bespoke two bedroom, luxury, self-catering accommodation in the county of Rutland, nestling in the delightful village of Empingham near the shores of Rutland Water. An ideal place to stay if you want to.....relax for a few days... …see more

Certificate of Excellence

from $126 / night

$878 - $1,386 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from $126 / 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
Primrose Hall is a homely cottage in the centre of the lovely village of Empingham, with parking immediately outside. A pub serving hot, home-cooked food is one minutes walk away and open all day. There is also a shop open 7 days a week, a doctors surgery and a hairdr …see more

Certificate of Excellence

from $90 / night

$641 - $997 / week

Book View

Responds fast!
avg. 1 hour 5 minutes

from $90 / night

(42) Very Good 

24

Stamford Vacation cottage rental

Rutland / Stamford

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Set in one of Rutland's many pretty villages, two chapel lane is an eighteenth century, stone-built Grade II listed cottage. Sleeping up to 6 (4 adults with 2 babies / toddlers), features include a wood burner, walled courtyard garden and complimentary wifi. Ideal for a …see more

from $113 / night

$786 - $1,122 / week

Book View

Responds fast!
avg. 1 hour 15 minutes

from $113 / night

(5) Excellent 

15

Vacation 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 $132 / night

$647 - $740 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $132 / night

(7) Very Good 

18

Vacation home in Uppingham

Rutland / Uppingham

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Corner House's central location makes all the facilities that the Market town of Uppingham has to offer readily available, without the need to drive. The Corner House is an ideal base to explore the activities in and around Uppingham which itself is an historic Mar …see more

from $159 / night

$839 - $984 / week

Book View

from $159 / night

(15) Excellent 

Certificate of Excellence

23

Vacation home in Stretton

Rutland / Stretton

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Moo Cow cottage on Stocken Hall farm is situated in the beautiful County of Rutland. Stylish, charming and homely would be the best way to describe this beautiful Farm Cottage which is tastefully decorated in a farm like theme and situated on an active working family fa …see more

Certificate of Excellence

from $132 / night

$660 - $1,083 / week

Book View

Responds fast!
avg. 1 hour 29 minutes

from $132 / night

(23) Very Good 

23

Vacation home accommodation

Rutland / Cottesmore

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
This is a spectacular detached 5 bedroom cottage with all amenities including a log burner for those chilly wintry nights. Luxury kitchen/diner, large lounge. Sleeps up to 9 people. 2 doubles both with en-suites, 2 twin rooms, 1 single room and a family bathroom. A …see more

from $218 / night

$918 - $1,532 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from $218 / night

(2) Excellent 

18

Vacation apartment in Manton

Oakham / Manton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
This two storey oak built cottage with bedroom and bathroom upstairs and a lounge with small kitchen downstairs has stunning views of Rutland water through full height french windows and is within a quiet village with a local pub serving good food. The property is on t …see more

from $99 / night

$594 - $825 / week

Book View

from $99 / night

(2) Excellent 

11

Vacation 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
Manton Lodge Farm is a beautifully positioned 18th-century stone farmhouse set in more than 100-acres of rolling grassland in rural Rutland. It boasts far-reaching views across the sweeping River Chater valley, and is a short distance from Rutland Water. The south fac …see more

from $132 / night

$502 - $700 / week

Book View

from $132 / night

(20) Excellent 

28

Oakham Vacation cottage rental

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 115 mi
  • Ask about children
  • Private garden
** Sister property to local Rutland thatched cottages: Sticky End, Cottesmore, Near Oakham, Rutland - Property No. 9749 + Little Thatch, Seaton, Near Uppingham, Rutland - Property No. 1130618 NB: All our cottages operate a strictly "Non-smoking" & "No pet …see more

from $131 / night

$687 - $1,228 / week

Book View

from $131 / 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
The Walled Garden holiday Cottage is a pretty, self-contained cottage that sits in a quiet, private garden in Barnsdale, in the heart of Rutland. Located just a minute's walk from the banks of Rutland Water, it's perfect for a weekend getaway or longer holiday, ideal fo …see more

from $103 / night

$740 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from $103 / night

(4) Excellent 

13

Vacation lodge in Exton

Rutland / Exton

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Sleeps 6: 3 x double or twin rooms Cuckoo Barn Lodge sits in an idyllic valley near Rutland Water. It is a perfect place to enjoy a wealth of activities, wine and dine, and pamper yourself. It sleeps six comfortably in 4 Star Gold luxury with extra beds available. A s …see more

from $152 / night

$825 - $2,008 / week

Book View

from $152 / night

(24) Excellent 

Certificate of Excellence

7

Stretton Vacation cottage rental

Rutland / Stretton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Private garden
Our comfortable stone built "newly furnished" self catering cottage which Is situated 1/2 mile from the A1 with off road parking. There are 2 Bedrooms with 1 Double Bed and 1 Zip/Link Twin bed, a fully fitted shower room, fully fitted kitchen and comfortable living area …see more

Certificate of Excellence

from $80 / night

$502 - $1,056 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $80 / 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
Moss Cottage Rutland sleeps up to 5 people comfortably, (there is also a sofa bed, if required) The newly renovated accommodation comprises two good-sized bedrooms, and one small single room, sleeping up to 5 people in total. There is also a sofa bed in th …see more

from $152 / night

$740 - $1,037 / week

Book View

from $152 / night

(13) Excellent 

31

Vacation apartment in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Car not necessary
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 $126 / night

$786 - $1,188 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from $126 / night

(17) Excellent 

29

Vacation cottage in Uppingham

Rutland / Uppingham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Private garden
'Chocolate Box' Luxury Thatched Cottage & Garden, 3 Bedrooms, Beautiful Local Walking & Cycling ** Sister property to local Rutland thatched cottages: Sticky End, Cottesmore, Near Oakham, Rutland - Property No. 9749 + Autumn Cottage, Preston, Near …see more

from $131 / night

$687 - $1,320 / week

Book View

from $131 / night

(12) Excellent 

23

Vacation cottage in Belton-in-Rutland

Rutland / Belton-in-Rutland

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 160 mi
  • Child friendly
  • Pet friendly
Waterend Barn is a delightful, wisteria and ivy covered cottage built with the golden sandstone so typical of Rutland. It is set in a small, well tended garden and provides guests with every comfort. There are fine views from the bedrooms and an excellent choice of wa …see more

from $113 / night

$786 / week

Inquire View

from $113 / night

(25) Excellent 

24

Edith Weston Vacation cottage rental

Rutland / Edith Weston

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 mi
  • Suitable for children age 5+
  • Pet friendly
Built in the 1850s out of local limestone with a typical Rutland Colleyweston slate roof, Postbox Cottage has an array of original features. The doorway to the bakery has been preserved, as have the beams of the loft, now forming the bedrooms and bathrooms, and in the …see more

from $119 / night

$660 - $825 / week

Inquire View

from $119 / night

(1) Excellent 

12

Vacation log cabin in Oakham

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 4 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard. Each …see more

from $108 / night

$590 - $1,193 / week

Inquire View

from $108 / night

(21) Excellent 

22

Vacation cottage rental

Rutland / Oakham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
** Sister property to local Rutland thatched cottages: Little Thatch, Seaton, Near Uppingham, Rutland - Property No. 1130618 + Autumn Cottage, Preston, Near Oakham/Uppingham, Rutland - Property No. 6555591 NB: All our cottages operate a strictly "N …see more

from $131 / night

$687 - $1,228 / week

Book View

from $131 / 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
This is a very well equipped detached a-frame lodge in the grounds of Barnsdale Hall Hotel on the bank of and with fantastic views of Rutland Water. It has 1 x double bedroom, 2 x twin bedrooms, kitchen diner and lounge. PLEASE NOTE; THIS IS MY TIMESHARE W …see more

Pricing unknown

Book View

Pricing unknown