Cottage holiday rentals in Oakham

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Top-rated cottage rentals in Oakham

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Top guest favourite
The country cottage is set on a spacious estate, surrounded by rolling green fields. The brick structure features a welcoming entrance with a covered porch and two dormer windows. A well-maintained, paved courtyard emphasizes the home's secluded and tranquil setting.
Cottage
4.96 out of 5 average rating, 388 reviews

NEW Luxury Romantic Cottage - Idyllic Rural Bliss

Brand New! Beautiful Romantic Country Cottage with private deck offering amazing rolling countryside views set on 14 acre estate. • Blissful tranquillity • Easy Access to A14, M1 & M6. • 10 mins to Market Harborough • Super King wide bed - Can split to 2 singles • Sofa bed - 1 adult or 2 kids Enjoy: • Fully Equipped Kitchen • 100MB Fibre Internet • Gas BBQ • Original Art • Luxury Linens • FREE Netflix, Disney+ & Xbox • Amazon Echo + Free Music • Air Conditioning + Underfloor Heating

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, 208 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
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, 151 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!

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, 165 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, 182 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
Cottage
4.99 out of 5 average rating, 350 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, 203 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.

Top guest favourite
A spacious kitchen features exposed wooden beams and stone flooring. A dining table with striped tableware is set for four, while modern appliances are arranged across the counters. Natural light floods in through multiple windows, illuminating the well-equipped cooking area.
Cottage
4.99 out of 5 average rating, 246 reviews

Beautiful Grade II Listed Barn Conversion

A beautiful Grade II listed stone barn with traditional & period features, but with all modern amenities. Comprised of 2 bedrooms & 2 bathrooms: one double-bed ensuite & a twin room. A traditional & well-equipped kitchen (inc washing machine & dishwasher). Flatscreen TV/DVD & Wifi. Access to own patio area with BBQ. Central heating and double glazing throughout. Parking outside the property with access to an electric charging point. Well behaved dogs (2 maximum) are welcome.

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. Electric charging point available.

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, 414 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.

Top guest favourite
A charming exterior view of the house is framed by large arched windows. Vibrant flower beds, featuring a mix of colors, border a gravel pathway. Outdoor seating is arranged nearby, inviting relaxation in a serene natural setting.
Cottage
5 out of 5 average rating, 151 reviews

Barn conversion set in 30 acres of nature reserve.

Relax in this peaceful, spacious house, set in it's own nature reserve - 30 acres of woodland and meadows. A chance to see nature, up close and personal - Barn owls, heron, deer, hare and lots more. Located in rural Leicestershire countryside, The Barn provides a tranquil base from which to explore the beautiful countryside, as well as those wanting to enjoy the boutiques and dine out in the old town of Market Harborough.

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, 189 reviews

Daphne's cottage

Comfortable entire self-catering home sleeping up to 4 guests. Enjoy a fully equipped kitchen, cosy underfloor heating, fast WI FI and onsite parking for 2 cars. Conveniently located just 2 minutes from A1 southbound. Perfect for contractors, dog walkers and weekend breaks. Nightly stays welcome. For Same-day bookings, Please kindly be made before 2 p.m. to allow time to prepare the property. Thank you for your understanding.

Popular amenities for cottage rentals in Oakham

Quick stats about cottage rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at £141 per night before taxes and fees

  • Verified guest reviews

    Over 290 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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