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Holiday houses in Cottesmore

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Top-rated holiday rentals in Cottesmore

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a charming 17th-century cottage is featured, showcasing a thatched roof and white-washed walls. Surrounded by greenery, the cottage has large windows with gray frames, and a gravel pathway leads to the entrance, enhancing its quaint appeal.
Cottage in Cottesmore
4.98 out of 5 average rating, 137 reviews

Quiet Lane Retreat: The Bee Cottage Rutland

Welcome to our charming cottage located on a tranquil lane in Rutland. Just a quick 5-min drive from Rutland Water, this 17th-century cottage is a picture-perfect gem that has undergone a refurbishment. The thatched roof adds to its undeniable charm. Step inside and be greeted by original features like low ceilings, doorways and exposed beams, creating an authentic atmosphere. The cottage comfortably accommodates up to 5 people, offering surprisingly spacious living. Enjoy free Netflix and WiFi.

Top Guest favourite
An open living area features high wooden beams and skylights, creating a spacious atmosphere. Two comfortable Chesterfield sofas in shades of blue are arranged around a wooden coffee table adorned with a floral centerpiece. A homely dining area is visible in the background.
Barn in Thistleton
4.96 out of 5 average rating, 108 reviews

Luxury Victorian Hayloft barn, newly converted.

You'll love this unique and romantic escape. Set behind fully private, electric gates in a quiet village. The Hayloft Barn is a newly converted first floor, Victorian barn where every care has been taken to retain the character whilst providing comfort and luxury for a relaxing stay. You will find a kingsize bed, roll top bath, huge walk in shower, chesterfield sofa's, smart tv and a fully equipped kitchen. Suitable for well behaved dogs, fully enclosed private garden with BBQ and fire pit.

Top Guest favourite
Tiny home in Warwickshire
5 out of 5 average rating, 135 reviews

The 4.50 from Paddington

Escape to a lovingly restored 1930s railway carriage set in the peaceful Warwickshire countryside. The 4.50 from Paddington is a one-of-a-kind stay with rustic charm and everything you need to unwind — from books and gramophone records, countryside views and a wildflower paddock. Walk to Draycote Water, or explore the wildlife-rich Lias Line just minutes from the door. Dog-friendly, with good Wi-Fi. Perfect for walkers, cyclists, sailors, and anyone who wants to experience a simpler life.

Top Guest favourite
Cabin in Dadlington
5 out of 5 average rating, 231 reviews

The Fuller's Shed All Weather Private Hot Tub

Adults only. 2 guests max. Sorry, No pets This cosy lodge offers a romantic haven for couples wanting to relax in peace. The luxury interior is styled to impress with every comfort catered for. Outside the covered veranda has a private hot tub, swing seat, outdoor hot shower and dining area where you can kick back and relax. Whether you want to stargaze, ramble, or relax, this is the ideal quiet venue with stunning sunsets and views over rolling countryside, horses, sheep and alpacas.

Top 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
4.84 out of 5 average rating, 328 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, pub 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
A Scandinavian-style cabin is shown nestled in a green yard, surrounded by trees. Steps lead up to the wooden door, which features an octagonal window. The cabin's natural wooden exterior blends harmoniously with the landscape, inviting exploration of the serene surroundings.
Place to stay in Greetham
4.97 out of 5 average rating, 130 reviews

Scandinavian Cabin in its own little wood.

Welcome to our Scandinavian cabin, set in a leafy glade where squirrels, hedgehogs, hares, wild ducks and pheasants roam safely. Explore the grounds & enjoy the peace. Private free parking on site. Continental breakfast included. There are two single beds in the cabin . There is space to pitch a 2 person tent next to the cabin at £20.00 per night. There is a fabulous pub in the village. Booking is essential. Sorry, we are unsuitable for children. Just 2 miles from the A1.

Top Guest favourite
A rustic shepherd's hut is nestled amidst greenery, framed by willow trees. A grassy area with outdoor seating is visible in front, alongside a wood-burning stove contributing to a cozy atmosphere. Smoke gently rises into the air, suggesting warmth and comfort.
Shepherd’s hut in North Witham
4.99 out of 5 average rating, 322 reviews

Little Oaks at Hillview

Beautiful, Luxurious, Home from Home Shepherds Hut. Nestling in its own fenced spinney with 300 year old Ash and Oaks trees around you, Little Oaks is rural, isolated and private. You can enjoy the wood fired hot tub, fire pit, BBQ or Pizza oven with only the sheep, goats, horses and chickens on our farm watching. Looking out over rolling countryside, our home built hut is cosy, beautifully appointed, and built to an exacting specification, somewhere we would love to stay!

Top Guest favourite
Cottage in Cottesmore
4.96 out of 5 average rating, 23 reviews

Plum Cottage, Cottesmore

Escape to a cosy countryside cottage in the peaceful village of Cottesmore, just a short drive from Oakham and Rutland Water. Ideal for couples, small families, or solo travellers, it blends rustic charm with modern comfort. Enjoy a bright living space, fully equipped kitchen, and restful bedrooms, plus a private outdoor area perfect for morning coffee or unwinding after exploring local walks and village pubs. A warm, homely base for a relaxing and memorable stay.

Guest favourite
A charming stone cottage with a red-tiled roof is surrounded by greenery. Large windows allow natural light to enter, while a small patio area with two metal chairs and potted plants sits in the foreground. The entrance features a dark wooden door.
Cottage in Rutland
4.88 out of 5 average rating, 206 reviews

Pantiles Cottage, Stretton, sleeps 4 self catering

Beautiful, recently renovated, detached stone cottage. Both bedrooms are en-suite, one with king sized bed the other twin zip and link beds, which can be used as a double if requested. Modern fully fitted kitchen diner and separate lounge. Free Wifi. Owners, Gill and Greg Harker live on site. Car parking for two cars. Stretton is 7 miles from Rutland Water, 8 miles from Oakham and 9 miles from Stamford and Burghley. Electric charging point available.

Top Guest favourite
The exterior of a charming converted barn is set against a clear blue sky. A gravel driveway leads to the entrance, bordered by neatly trimmed hedges. The structure features a mix of brick and wood finishes, with a covered entryway and green landscaping enhancing the rural setting.
Barn in Whissendine
4.99 out of 5 average rating, 178 reviews

Beautiful Conversion in Rutland Countryside

Come and stay in our lovingly converted barn in the middle of the Rutland countryside. Perfect for a quiet get-away with lots of walking and cycling from the doorstep. Set in a 3 acre plot of our family home, you will have access to a private garden at the rear of the property plus our orchard should you wish to bring 1 small - medium sized dog with you. Unfortunately, the property is not suited to large dogs.

Top Guest favourite
The exterior of a charming 19th century barn is showcased, featuring a stone facade adorned with climbing wisteria. Two wooden doors frame the entrance, complemented by two symmetrical windows above. A gravel area leads up to the building, enhancing the quaint rural aesthetic.
Guesthouse in Clipsham
4.93 out of 5 average rating, 138 reviews

Spacious 2 bed barn conversion in Rutland

This 19th century converted barn offers spacious and cosy accomodation and is situated next to the renowned award winning Olive Branch restaurant and is a quick 15 minute drive to central Stamford and Burghley House. Church Barn is a 6 minute drive to the sublime wedding venue of Holywell Hall. Church Barn is an old building with imperfections to be expected. Pets by prior agreement

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
4.94 out of 5 average rating, 338 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).

Popular amenities for Cottesmore holiday rentals

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