Holiday houses in Uppingham

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.

Value · Location · Wi-Fi

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

Family · Location · Access

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.

Location · Family · Hiking

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.

Location · Value · Checkout

The Old Bookshop

A unique one bedroom property. The Old Bookshop lies in the heart of historic Uppingham a short drive from beautiful Rutland Water offering walking, cycling, birdwatching and sailing. Recently refurbished by the interior decorator owner and still laden with books, it nestles in the heart of the town, with a distinctive style of it's own The book lined living area leads directly into a simple but well equipped kitchenette, onwards to a gorgeous bedroom with en-suite shower room.

Location · Family · Beach

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.

Family · Location · Accuracy

No. 34b

No. 34b is located in the centre of the historic market town of Uppingham which hosts a wide range of independent shops, restaurants and cafes and is within a few minutes walk from Uppingham School. A self-contained first floor apartment with open plan living, separate bedroom and ensuite. Having recently been decorated and refurbished to a high standard, this first floor apartment is a perfect choice for couples. (Maximum of 4 people (sofa bed in living area).

Location · Family · Cleanliness

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

Value · Family · Laundry

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.

Location · Family · Condition

Independent, private studio - rural with garden

Beech Barn is a cosy, rustic studio apartment in a lovely rural setting with superb views and yet walking distance to a great pub with restaurant and a village store. The room has a private patio, Wifi, Smart tv, seating area, en suite shower as well as a small kitchenette with kettle, toaster, fridge, microwave. The space is entirely independent and there is parking onsite.

Location · Family · Heating

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.

Family · Location · Layout

Stunning Thatched Barn- Newly renovated, High Spec

Nestled in the grounds of Cedar House, Cedar barn has been tastefully renovated to an extremely high specification. This stone thatched barn is the perfect location to take it easy at this tranquil and unique getaway. Perfect for exploring Rutland Water, Stamford, Uppingham + Oakham.

Location · Value · Quiet