Family-friendly holiday rentals in Oakham

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. The fenced garden has a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included

Lovely Cottage In Pretty Village Nr Rutland Water

Gable Cottage is in the picturesque village of Braunston-in-Rutland. A unique two bedroom cottage annexe, with bath and shower. Dining room with kitchenette (air fryer, microwave, toaster, kettle), and cute gallery sitting area overlooking it. Breakfast welcome pack included, we make our own bread! Access via private lane, parking for 2 cars. We also have an electric car charger Children over 10 welcome, no pets. Discount of £30 a night if only want one bedroom - message us before booking.

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.

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.

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.

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.

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.

Clock Cottage Self contained Rutland Rural Retreat

Clock Cottage is a self contained open plan suite located on the ground floor with garden views located within a characterful rural village within a 5 minute drive from Rutland water. The suite is open plan and includes a king sized bed, comfy living area and kitchen, Nespresso coffee machine, freestanding open plan bathtub and separate bathroom and outside dining area. The living area can be used as a family/friends bedroom with the use of a fold out sofa bed. Ideal for a couple.

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.

Cosy luxury glamping pod Rosina.

Located in the heart of rural Leicestershire, our luxury glamping pods are the perfect location for a country getaway. With a permenant double bed and the option of a second pull out double bed we cater for either a couple or group of four. Self catering facilities, a fully fitted shower room, a TV and WiFi combined with an extensive network of foot paths, bridle ways and national cycle routes makes our pods the perfect hub for your country escape.

New Lodge Cabin

A cabin on wheels, made from locally sourced oak and larch. Set within a meadow, surrounded by woodland in Sherwood Forest. Shower with underfloor heating in a shepherd hut. Compost toilets. Outdoor pot washing facilities and dining area. A perfect off grid stay. Our smallholding has sheep, goats and chickens which graze often in the meadow depending on the season. Sherwood Forest and Sherwood Pines are all within walking/cycle distance.

Fennel House. Charming house in Oakham town centre

The townhouse is located on a quiet residential one way street. Oakham has stunning historical architecture, i.e a castle, quaint independent shops, pubs and restaurants are moments from the door. A short walk from the railway station. It is ideal for couples or families. A short drive is Rutland Water and is the largest man made lake in Europe 26 miles circumference and hosts many outdoor pursuits such as walking, cycling and bird watching.