Holiday houses in Uppingham

4.99 out of 5 average rating, 147 reviews

Townhouse in Manton

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. There is a garden with a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included.

4.81 out of 5 average rating, 197 reviews

Home in Rutland

Cherry Tree Cottage

Cherry Tree Cottage is a delightful and spacious yet cosy stone barn conversion situated in the peaceful and picturesque Rutland village of Seaton only 2 miles from the historic market town of Uppingham. The property has bi-folding doors opening out onto a completely private enclosed garden. There are beautiful walks exploring the Welland Valley from the property including to the impressive Harringworth viaduct only a mile away. It is the ideal location to explore what Rutland has to offer

5 out of 5 average rating, 188 reviews

Cottage in Stoke Albany

Converted Barn overlooking fields.

Built in 1634, the Barn is on the edge of a village 5m from Market Harborough in Leicestershire. Converted in 2017, it's on our property but separate from it. Light and airy, it's one room/open plan downstairs, with areas for cooking, dining and relaxing. French doors lead out onto a pretty courtyard garden, with stone steps up to a raised area, where you can watch the sunset over the fields. Upstairs there's a well-equipped bedroom and bathroom with far reaching views over the countryside.

4.97 out of 5 average rating, 102 reviews

Condo in Uppingham

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

Superhost

Apartment in Rutland

4.87 out of 5 average rating, 266 reviews

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.

4.92 out of 5 average rating, 160 reviews

Condo in Uppingham

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.

4.94 out of 5 average rating, 106 reviews

Apartment in Medbourne

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.

4.96 out of 5 average rating, 308 reviews

Home in Manton

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.

4.85 out of 5 average rating, 287 reviews

Cottage in Wing

Idyllic Thatched Country Cottage - a hidden gem!

Situated in the picturesque village of Wing, this adorable thatched cottage is nestled in the grounds of beautiful Cedar House. The property was fully renovated in March 2021 and is the ideal getaway location to explore everything that stunning Rutland has to offer. The cottage is only 5 minute drive to Rutland Water, Uppingham and Oakham, so you have everything you wish to experience during your stay on your doorstep. Historic Stamford is also only 20 mins away.

4.95 out of 5 average rating, 134 reviews

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.

4.88 out of 5 average rating, 266 reviews

Cottage in Wing

Quiet Rural Chapel Conversion (Architectural Gem)

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" & won a local design award Helpful owners next door Completely OPEN PLAN INTERNAL WALLS ONLY AROUND BATHROOM

4.91 out of 5 average rating, 326 reviews

Cottage in Uppingham

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.

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4.98 out of 5 average rating, 364 reviews

Condo in Gretton

St James’s Cottage - Gretton

GeoffRating, 5 stars2 weeks ago

We really enjoyed our stay here. It is a beautiful part of the country. Apartment was clean and spacious. Nice homely touches. Everything you could need in the kitchen and the separate lounge/kitchen room was a bonus.

Cottage in Caldecott

5 out of 5 average rating, 9 reviews

Pond Cottage at the Old Vicarage

SallyRating, 5 stars2 weeks ago

Beautiful cottage in a lovely area, perfect for a peaceful getaway. Everything you need in the kitchen including jams , marmalade and sauces for the all important fried breakfast ! Will be booking again!

5 out of 5 average rating, 4 reviews

Uppingham bolthole

VeraRating, 5 stars2 months ago

Alexandra was very friendly and helpful! She gave us local recommendations and was easy to communicate with. Check in was very simple and the house is very cosy. Great place to stay in!

Cottage in Caldecott

4.77 out of 5 average rating, 114 reviews

Thatch 1 bed cottage. Period features.

KimberleyRating, 5 stars4 weeks ago

Beautiful cottage in an idyllic village. Jane is a fantastic host, even providing a range of board games! The perfect weekend spent relaxing.

5 out of 5 average rating, 74 reviews

Home in Grantham

The Garden House at Hungerton

MaryRating, 5 stars3 weeks ago

As soon as we saw the Garden House we relaxed straight away, it is a perfect place to unwind and enjoy the beautiful scenery and birds. Isabel’s handbook had lots of information and great instructions to walk around the estate and meet the sheep. The welcome pack was superb! Thankyou! We slept so well with the bird song waking us. We did venture out but it was great to get back to the comfort of the Garden house. I met Isabel who is a wonderful lady. We do hope to be back again Mary and David

5 out of 5 average rating, 3 reviews

Cybil's Retreat- 2 bed house with enclosed garden

BrynRating, 5 stars21 months ago

We were delighted with our stay at Emily’s place. The house was perfect with a lovely garden that was enjoyed by our dog as well as us! Perfect to have a a friendly pub next door and easy to walk through the pretty town of Uppingham. It was also easy to get to various starting points for walks around Rutland Water. We highly recommend this cottage.