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Holiday houses in Rutland

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Top-rated holiday rentals in Rutland

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Top Guest favourite
A rustic wooden sign is mounted on a metal bracket, displaying the name 'St. James's Cottage.' The sign is attached to a stone wall with visible texture, and utility lines are present in the background.
Condo in Gretton
4.98 out of 5 average rating, 409 reviews

St James's Cottage – Gretton

An independent, first floor, apartment in a 200yr old cottage. 1 bedroom available as superking bed or twin beds. Separate living room with kitchenette, combination microwave/oven/grill, single zone hob, toaster, kettle and full size fridge. Bathroom with shower. Free WiFi. Private, off road parking outside cottage. Secure garage space available upon request, for locking up bicycles, fishing tackle, golf clubs etc. Set in a lovely, quiet, village with two pubs & coffee shop in walking distance.

Guest favourite
A stone cottage features a sloping roof and large glass doors opening to the garden. A wooden pergola, supported by beams, adorns the outdoor seating area. Lush greenery and lavender line the property, enhancing the peaceful countryside setting.
Tiny home in Ketton
4.81 out of 5 average rating, 107 reviews

Beautiful and Quaint Converted Stable in Rutland

This Grade-2 Listed, self-contained, dog-friendly cottage is the perfect hideaway for a couple looking to enjoy the beautiful Rutland countryside. Ketton is only a few minutes drive from the beautiful town of Stamford, or Rutland Water with its stunning views and local Ospreys. Oakham is also a short drive away. There's a Camra award-winning pub a few minutes walk away and plenty of circular walks in the surrounding countryside, from the accommodation or further afield, to work up a thirst.

Guest favourite
The image captures a serene village scene, featuring charming stone cottages nestled among lush greenery. The majestic church tower rises in the background, adding architectural interest. A pathway winds gently through the area, inviting exploration of the picturesque surroundings.
Cottage in Ketton
4.94 out of 5 average rating, 145 reviews

Churchyard Ketton stone cottage next to the pub

Eighteenth century Ketton stone cottage nestled in the churchyard near the CAMRA award-winning and fabulous Railway Inn. Wood burner, three double/twin rooms, White Company bedding, nearby village vineyard & great food scene, Burghley House ten minutes away, Rutland Water three miles away; England's finest stone town,Stamford, ten minutes. Whether you are a group of three couples, a family or a couple wanting a romantic getaway, this is a great blend of a countryside retreat and great fun!

Guest favourite
Religious building in Wing
4.88 out of 5 average rating, 298 reviews

The Chapel

Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" , on TV & won a local design award New for 2025-advanced ai heating system Owners next door COMPLETELY OPEN PLAN Internal walls around Bathroom only.

Top Guest favourite
The exterior of a stone barn conversion features a distinct pitched roof and a charming facade. The building is marked by weathered stonework and traditional details, including a chimney and a welcoming entrance, set against a clear blue sky.
Cottage in Empingham
4.99 out of 5 average rating, 179 reviews

Primrose Hall Holiday Cottage Rutland

Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, pub, medical centre, and an antique shop just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

Guest favourite
A grassy outdoor space is bordered by neat hedges, contrasting with the lush green hills in the background. The bright sky features scattered clouds, enhancing the tranquility of the rural setting.
Tiny home in Empingham
4.83 out of 5 average rating, 298 reviews

Lower Farm View - Perfect For 2

Lower Farm View is beautifully converted with outstanding views, it's situated in the Rutland Village of Empingham and is only a short walk from Rutland Water's North Shore. Only 6 miles from the beautiful Georgian town of Stamford and 6/7 miles from the picturesque towns of Uppingham and Oakham. The village itself has a hairdresser, doctor's surgery, and shop. The local area has lots of pubs, cafes and shops. A perfect place to be able to enjoy and explore the county of Rutland.

Top Guest favourite
The stone-built cottage is set in a rural environment, featuring a welcoming green front door framed by lush foliage. A gravel driveway leads to the entrance, with decorative stone planters and a small fenced area to the side populated with greenery.
Cottage in Rutland
4.95 out of 5 average rating, 185 reviews

Daphne's cottage

Our comfortable self-contained cosy dwelling of traditional build located in a rural village just North of Stamford. A stone throw away from the A1 leading you to points of attraction such as Stamford, a beautiful historic town center. Rutland water, "the largest man made lake in the UK" that is perfect for outdoor activities. Belton Estate, part of the National trust. Keen cyclists are able to store their bicycles safely away in our key lock garage (subject to pre-arrangment)

Guest favourite
The kitchen features a double Belfast sink and handcrafted cabinetry, highlighted by warm, natural light filtering through the window. Exposed ceiling beams complement the neutral tones of the stylish design, while a potted plant adds a touch of greenery to the inviting space.
Condo in Uppingham
4.91 out of 5 average rating, 115 reviews

Central Character/Contemporary Apartment

Set within walking distance to Uppingham’s bustling town centre is this stunning central ground floor apartment full of character and original features creating an ultimate holiday experience. Guests will enjoy two spacious double bedrooms, built in wardrobe, hand crafted breakfast kitchen, exceptional shower room, subtle design touches and beautiful courtyard garden. Free parking is available 2-3min walk away from the property. There is also 2hrs free parking to the front.

Top Guest favourite
A charming garden is illuminated by soft lights, showcasing a path leading to a thatched-roof building. The well-maintained green space features neatly arranged plants and shrubs, with a birdbath as a focal point. The atmosphere suggests a tranquil evening setting.
Home in Manton
4.96 out of 5 average rating, 384 reviews

Oak Tree Annexe

Oak Tree Annexe is set in a secluded and secure walled garden. You can park for free directly outside the house and will be staying in one of Rutland’s most desirable villages. Set on the fabulous cycle route around the water and with access to great walks directly from the house or a short drive away it’s a perfect location for exploring Rutland. Our village pub is a 3 minute stroll, serves food 7 days a week and offers our guests a 10% discount on their meals.

Top Guest favourite
A charming living space features exposed brick walls, accented by elegant mirrors. A spacious bed with soft pillows is flanked by bedside tables, and a cozy sofa is complemented by a bright yellow cushion. Light spills in from a window with muted curtains.
Barn in Uppingham
4.93 out of 5 average rating, 101 reviews

Topiary Barn - Stylish Accommodation in Rutland

Stylish holiday accommodation located in a beautiful topiary garden behind Uppingham Antiques Centre. Garden studio designed for 2 guests. In cosy living space with wood burning stove, WIFI, newly fitted kitchen and ensuite with modern interior and statement antiques located in the stunning market town of Uppingham in England's smallest county of Rutland. Within 4 miles of Rutland Water

Top Guest favourite
An open-plan living area features a spacious bed and a sofa, accompanied by a cozy rug. Natural light filters through the large windows, which are dressed with cheerful yellow curtains. An inviting fireplace adds warmth to the space, complemented by simple decorative elements.
Apartment in Ketton, Stamford, Lincs
4.94 out of 5 average rating, 330 reviews

Private Apartment in the Heart of Ketton, Stamford

Relax and unwind in the spacious, private apartment with garden in the beautiful village of Ketton. Close to Stamford, Rutland Water and Burghley House. One double bed plus one sofa bed (sleeps 2) in open plan apartment with fully fitted kitchen and private bathroom. 3 miles to the A1 / 4 miles Stamford / 20 mins Peterborough with direct trains to London Kings Cross (50 mins).

Guest favourite
The entrance to the property is framed by lush greenery and colorful flowers, creating a vibrant and inviting exterior. A set of steps leads to two light green doors, flanked by decorative plants and pots. The original stone facade of the building adds character.
Cottage in Uppingham
4.91 out of 5 average rating, 339 reviews

Number 4, Pleasant Terrace, Uppingham, Rutland

No.4 is close to the centre of Uppingham. You’ll love No.4 because of the views over open countryside at the back whilst being within a 5 minute walk of the towns restaurants and pubs. No.4 is good for couples and business travellers. Parking is unrestricted on the road outside. Pleasant Terrace is a Cul-De-Sac so no passing traffic and it is very quiet and peaceful at night.

Popular amenities for Rutland holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Rutland