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.

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

Luxury apartment with outstanding views

We created a self catering studio apartment from our hay loft during the lockdown of 2020. In the heart of the Welland Valley in Leicestershire there are are wonderful views up the hill to Nevill Holt (home of the Nevill Holt Opera Festival) and from the sofa you will be able to watch the sun setting behind the hill. Many miles of footpaths on the doorstep. There is a heated pool open May-Sept and a tennis court. Please ask us regarding access. Check out our guidebook for things to do

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.

The Snug

A self-contained annex of 350 year old grade II listed country cottage in the beautiful Rutland village of North Luffenham, close to Rutland Water and historic towns of Stamford, Oakham and Uppingham. Accommodation is perfect for two or a small family with one child, consists of entrance hall with utilities leading up to double bedroom, and shower room on the first floor, and down to kitchen, lounge , working fireplace on the ground floor. An extra single bed available on request.

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.

Charming cottage in picturesque country village

Entire private flat within charming cottage situated in picturesque country village. 10 mins from Market Harborough train station. (Only 1 hr from St Pancras Station.) Half an hr from Stamford & Rutland Water and only 10 mins from small market town of Uppingham. We offer two interconnecting double bedrooms with shower room and kitchenette with dining table in family home. First Bedroom on 1st floor and 2nd bedroom on second floor, within apartment. Tea, coffee and milk provided.

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.

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.

Independent, private studio - rural with garden

Beech Barn is a very comfortable and peaceful space 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 and induction hob.