Family-friendly vacation rentals in Rutland

St James’s Cottage - Gretton

An independent, first floor, apartment in a 200yr old cottage. 1 bedroom available as superking bed or twin beds. Separate living room with kitchenette, combination microwave/oven/grill, single zone hob, toaster, kettle and full size fridge. Bathroom with shower. Free WiFi. Private, off road parking outside cottage. Secure garage space available upon request, for locking up bicycles, fishing tackle, golf clubs etc. Set in a lovely, quiet, village with two pubs & coffee shop in walking distance.

A Magical Hobbit House In Rutland

A unique quaint ‘Hobbit House’ nestled in the heart of Rutland/Stamford Looking for a cosy romantic getaway or a magical adventure getting closer to nature, then this is the place for you. Stepping inside, it really has the wow factor, offering something that little bit different from the rest. Close to Burghley house, a host of local pubs/restaurants and endless nearby activities. A self catering accommodation with home from home facilities and close to all amenities. It’ll make you smile!

Beautiful and Quaint Converted Stable in Rutland

This Grade-2 Listed, self-contained, dog-friendly cottage is the perfect hideaway for a couple looking to enjoy the beautiful Rutland countryside. Ketton is only a few minutes drive from the beautiful town of Stamford, or Rutland Water with its stunning views and local Ospreys. Oakham is also a short drive away. There's a Camra award-winning pub a few minutes walk away and plenty of circular walks in the surrounding countryside, from the accommodation or further afield, to work up a thirst.

Peaceful hidden hut based in the heart of Stamford

Adventure awaits you in this rustic and romantic getaway. The hut is based in a very quiet location on the edge of Stamford town centre. All of your home facility needs will be provided including, air fryer/microwave/fridge/kettle/running hot and cold water/shower/toilet/hand basin/heated radiator/double bed, sofa bed and bedding/EETV and Wi-Fi. Free parking and private entrance through a gate at the back of the house. Extra amenities include - travel cot, blankets and dog bed and bowls.

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.

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, 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.

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.

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.

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.

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.