Holiday houses in Oakham

Hunky Dory Cottage, Central Oakham, Rutland

Our recently renovated 'home from home' is situated in the heart of Oakham with the boutique shops of Mill Street and many cafés, bars and restaurants of Oakham on its doorstep. The castle & park are an easy walk away as are all the towns amenities & attractions. The cottage is surrounded by roses and has been decorated by the owner, Jane, in her own unique style. All 3 beds are king size making it ideal for small families or up to 3 couples with good size dining room, lounge and a new kitchen.

The Hoot Rutland

Escape to The Hoot, a peaceful holiday cottage on the edge of Rutland Water. Swap your alarm clock for nature's wake-up-call - the hooting of owls in the bird sanctuary. Explore everything beautiful Rutland has to offer - from birdwatching to fishing, cycling, walking and sailing. Our one-bedroom holiday cottage, set in a large, private garden, minutes from Oakham. Sleeping 2 in either a double or two singles. In Summer, we do weekly holiday lets - more details and availability Thehootrutland.

Hastings Cottage

Hastings Cottage - a beautifully presented and newly refurbished annexe in an old Pub. Self contained, with shower room, Kingsize bed, own front door, WiFi, TV and kitchen with fridge, microwave and hob. 2 min walk to the centre of Oakham, pubs, restaurants and cafes. We have two electric assist bikes you can hire whilst you are with us, please book in advance. £35 a day each with a refundable deposit. Max two people - well behaved dogs are welcome - just let me know in advance. £10 a dog.

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.

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.

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.

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.

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.

Cozy Nook Boutique Cottage

Due to the huge success of Honeysuckle House my other holiday home in Oakham I have added Cozy Nook, an easy 10 minute walk from Oakham train station and Oakham High street with its many cafes and restaurants. Enjoy everything Oakham has to offer, spend your days discovering the surrounding area as there are many things to see and do nearby. Cozy Nook is a perfect hideaway for relaxing and exploring our beautiful county of Rutland.

Rutland, Outdoor Copper Bath & Cosy Log Burner

Nestled in the picturesque village of Edith Weston, this cottage boasts a courtyard with a outdoor copper bath, two cosy bedrooms, a comfortable living and dining area, and a fully equipped kitchen. Just a short stroll from the beautiful Rutland Water, it’s the ideal getaway for nature enthusiasts and anyone looking for some peace and quiet ,all while being close to various local attractions and towns. Insta: @theoldforge_rutland

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.

Mayfield - 1 bedroom annexe flat

Kick back and relax in this calm, stylish space. Private annexe flat with its own access. Open plan kitchen and living area. Separate dining area. 1 bedroom with zip link beds, can either be twin or superking. Bathroom with shower. Hallway. Access to washing machine, tumble dryer and clothes airer on request. Lockable storage for push bikes on request. Outside patio area.