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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, 134 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, 202 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.

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, 149 reviews

Spacious, character 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, 154 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, 171 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 exterior of Hardwick Lodge Barn is showcased in soft evening light, highlighting the brick façade and expansive bi-folding doors. A spacious south-facing patio extends from the house, framed by a large lawn and gardens, with a premium gas BBQ and seating area visible.
Cottage
4.98 out of 5 average rating, 266 reviews

Hardwick Lodge Barn - Guest House in Rural Setting

Hardwick Lodge Barn is a beautifully converted barn blending contemporary style with rustic charm. Nestled in a rural location, it offers a tranquil retreat surrounded by picturesque countryside. Polished concrete floors and bi-folding doors provide natural light and openness, while original oak beams add character. Relax by the log burner or explore Northamptonshire's beauty. Designed for comfort and style, the Hardwick Lodge Barn is ideal for a rural escape with modern amenities.

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
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)

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, 334 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.

Top 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, 316 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
The exterior of the converted barn showcases arched wooden doors and windows, framed by warm red brick. A paved area extends in front, reflecting the countryside views and open sky, enhancing the serene atmosphere of the location.
Cottage
4.95 out of 5 average rating, 110 reviews

The Victorian Barn

The Victorian Barn is a beautifully converted barn which provides a high standard of self-catering holiday accommodation for up to 4 guests. It is in a tranquil location amongst acres of arable farmland and wild flower margins. It can be easily accessed from the village of Theddingworth. Only 5minutes drive from the picturesque town of Market Harborough with a varied selection of restaurants, individual boutiques, award winning farm shop and covered market.

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, 381 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
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
4.91 out of 5 average rating, 336 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 cottage rentals in Oakham

Quick stats about cottage rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at € 147 per night before taxes and fees

  • Verified guest reviews

    Over 250 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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