Holiday houses in Uppingham

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

Elegant 3 bed High Street apartment in Uppingham

A spacious and elegant 3 bed apartment on the middle floor of a Grade II listed Georgian house in the heart of historic Uppingham. This spacious home has been lovingly restored and is stylishly decorated and furnished to a high standard. 2 comfy double beds and 1 single bed with good quality mattresses. A spacious lounge. Full kitchen , table and chairs for 5, dishwasher and microwave and starter essentials provided, tea & coffee, wash up liquid, dishwasher tabs etc. FREE HIGH SPEED BT Wi-Fi

Unique Countryside hideaway

Unique rural retreat perched on a hill in open countryside with breathtaking views. The Retreat is a self-contained 3 bedroom home adjacent to our barn conversion in 13 acres. The barn was converted by ourselves over two levels - one ground floor and one underground (don't worry it is very light and airy on the lower floor!) The perfect place for a countryside getaway to totally relax and unwind. Great walking and cycling on your doorstep or just switch off, chill out and enjoy the space.

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.

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.

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.

Comfy Modern APT - Sleeps 4

Located in the centre of the Historic Market Town of Uppingham. Based in is heart of the small county of Rutland. This apartment is a stones throw away to the gorgeous town centre, with markets every Friday, great places to eat and drink and some really cute little shops. A quick 10 minute drive to another Market Town of Oakham and not far from Rutland Water where you can enjoy some beautiful scenic walks. The apartment offers an allocated parking space and communal paved garden.

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.

36 High Street West -two bedroom luxury terrace

The property is set in the heart of this popular market town opposite the historic Uppingham School. It is perfect for any visitors to the school and is a short walk from the town's amenities which include a good range of independent shops and eating establishments. It is a spacious two bedroom house with a large, beautiful kitchen/ dining space and sheltered walled courtyard garden. The house has been decorated and furnished to a high standard.

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.

Topiary Barn - Stylish Accommodation in Rutland

Stylish holiday accommodation located in a beautiful topiary garden behind Uppingham Antiques Centre. Garden studio designed for 2 guests. In cosy living space with wood burning stove, WIFI, newly fitted kitchen and ensuite with modern interior and statement antiques located in the stunning market town of Uppingham in England's smallest county of Rutland. Within 4 miles of Rutland Water