Family-friendly holiday rentals in Oakham

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.

Indoor spaces · Kitchen · Hospitality

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.

Kitchen · Indoor spaces · View

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.

Kitchen · Family · Comfort

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.

Family · Kitchen · Comfort

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.

Indoor spaces · Family · Cleanliness

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.

Kitchen · Indoor spaces · Biking

Central Character/Contemporary Apartment

Set within walking distance to Uppingham’s bustling town centre is this stunning central ground floor apartment full of character and original features creating an ultimate holiday experience. Guests will enjoy two spacious double bedrooms, built in wardrobe, hand crafted breakfast kitchen, exceptional shower room, subtle design touches and beautiful courtyard garden. Free parking is available 2-3min walk away from the property. There is also 2hrs free parking to the front.

Kitchen · Indoor spaces · Quiet

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.

Indoor spaces · Family · Pets

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.

Indoor spaces · Family · Walkability

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.

Kitchen · Family · Parking

Sleepover with Miniature horse Basil

Basils Barn is situated on the grounds of a 17th century manor, surrounded by a picturesque 60 acre estate. The bedroom is directly attached to Basils stable, where there is a doorway in between the two spaces. In the paddocks we also have a herd of Highland cows, Hebridean sheep, horses, pigs, chickens and Norwegian Forrest cats. Our animals are mostly rescued and all of our animals are kept strictly as pets.

Family · Indoor spaces · Breakfast

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.

Indoor spaces · Kitchen · Cleanliness