Cottage holiday rentals in Oakham

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Top-rated cottage rentals in Oakham

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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
4.98 out of 5 average rating, 136 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
A pathway is lined with lavender plants leading up to the Barn, which is framed by greenery and trees. The stone structure features large, inviting windows that open onto the garden, enhancing the serene countryside setting.
Cottage
5 out of 5 average rating, 205 reviews

Converted Barn overlooking fields.

Built in 1634, the Barn is on the edge of a village 5m from Market Harborough in Leicestershire. Converted in 2017, it's on our property but separate from it. Light and airy, it's one room/open plan downstairs, with areas for cooking, dining and relaxing. French doors lead out onto a pretty courtyard garden, with stone steps up to a raised area, where you can watch the sunset over the fields. Upstairs there's a well-equipped bedroom and bathroom with far reaching views over the countryside.

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
4.95 out of 5 average rating, 146 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
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
4.88 out of 5 average rating, 205 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. Next door is the Jackson Stops Inn, which unfortunately has closed recently.

Top guest favourite
A charming cottage exterior showcases a brick and stone facade, framed by colorful flowering plants. Sunlight bathes the entrance, which features a wooden canopy. Windows offer glimpses into the interior, surrounded by a well-maintained garden with vibrant blooms.
Cottage
4.99 out of 5 average rating, 157 reviews

Beautiful cottage in village location

Located in a small village with beautiful countryside views, this spacious, 150 year old character cottage is self-contained with a garden to the front and a courtyard to the rear. It has two bedrooms, a newly refurbished bathroom, beamed living room and spacious kitchen diner. The cottage is 7 miles north of Melton Mowbray on the Notts / Leics border. Originally converted from a barn in the 1850s, it has been recently refurbished to a high standard but still retains many original features.

Top guest favourite
The image showcases the exterior of Castle Garden Cottage, featuring red brick and whitewashed walls. A gravel path leads up to the entrance, framed by window boxes filled with flowers. The garden area displays lush greenery and is bordered by trees, providing a serene environment.
Cottage
4.96 out of 5 average rating, 162 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, is located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

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
4.99 out of 5 average rating, 180 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.

Top guest favourite
The bathroom features a large copper bath set against exposed brick walls and timber beams. Natural light enters through a skylight and the space is complemented by antique-style decor, with fluffy white bathrobes hanging and decorative framed prints on the walls.
Cottage
4.99 out of 5 average rating, 344 reviews

Granary Digby, Luxury rural cottage nr Lincoln

Luxury self-catering accommodation on the border of the Lincolnshire limestone heath and the Witham valley. Centrally located at the heart of rural Lincolnshire, and only a 12 mile drive from The city of Lincoln. The Granary is a beautifully converted Lincolnshire barn, bursting with character and the perfect location from which to explore this historic county. Situated on the very edge of the rural village of Digby, the Granary forms one side of the original yard and stables.

Guest favourite
A private patio area features a circular stone surface, accompanied by two metal chairs. The brick exterior of the contemporary conversion is visible, with large patio doors leading into the living space. Lush greenery surrounds the garden, enhancing the tranquil setting.
Cottage
4.95 out of 5 average rating, 202 reviews

Willow Cottage

The accommodation was once a barn dating back to 1900. It is a contemporary conversion within the rear garden of the main house. The property incorporates everything needed for a great stay. It is completely private and self-contained. The ground floor consists of an open plan living room/kitchen and is accessed by two large patio doors. A staircase leads to a light and airy bedroom with a king size bed, drawers and a wardrobe. There is an en-suite bathroom with walk-in shower.

Guest favourite
A charming thatched cottage exterior is framed by a gravel drive and manicured greenery. Large windows allow natural light to fill the interior, while a subtle mix of stone and thatched roofing contributes to the cottage's historic character.
Cottage
4.86 out of 5 average rating, 328 reviews

Idyllic Thatched Country Cottage - a hidden gem!

Situated in the picturesque village of Wing, this adorable thatched cottage is nestled in the grounds of beautiful Cedar House. The property was fully renovated in March 2021 and is the ideal getaway location to explore everything that stunning Rutland has to offer. The cottage is only 5 minute drive to Rutland Water, Uppingham and Oakham, so you have everything you wish to experience during your stay on your doorstep. Historic Stamford is also only 20 mins away.

Top guest favourite
A spacious courtyard is framed by rustic buildings with red brick and whitewashed walls. Vibrant red foliage climbs the exterior, providing a striking contrast to the greenery. A small seating area with white chairs and a table invites relaxation in this tranquil rural setting.
Cottage
4.93 out of 5 average rating, 399 reviews

Lovely cottage in outstanding rural location.

Self contained accommodation, private entrance in beautiful rural setting. Sitting room with log burner and kitchen with oven, fridge, microwave and Nespresso machine. Two bedrooms with shared bath / shower room. We allow up to 2 dogs. We also offer a fully enclosed half acre paddock for exercising them. No street lights so it is a perfect location for stargazing. Village pub 5 mins walk away. Local for Stamford, Belvoir Castle, and Burghley House.

Guest favourite
A charming cottage is featured, showcasing a stone facade with white framed windows. Adjacent to a larger building, the cottage stands out with its rustic appeal, surrounded by a low stone wall. A peaceful atmosphere is emphasized by the clear sky and trees in the background.
Cottage
4.88 out of 5 average rating, 192 reviews

Holts Cottage in the Heart of Charnwood Forest

A Grade 2 listed one bedroom self catering cottage in the Heart of Charnwood Forest, set in the idyllic village of Woodhouse Eaves. A fantastic location for anybody visiting the Charnwood Forest area, the Cottage is in minutes walk from pubs, restaurants, cafes and shops. We are close by to the Great central railway and John's House - a Michelin Star restaurant. We offer a discount weekly and monthly.

Popular amenities for cottage rentals in Oakham

Quick stats about cottage rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at £119 per night before taxes and fees

  • Verified guest reviews

    Over 270 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakham rentals

  • 4.9 Average rating

    Oakham stays are highly rated by guests – averaging 4.9 out of 5!

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