Holiday rentals in Oakham

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Top-rated holiday rentals in Oakham

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Guest favourite

Cottage in Wing

4.88 out of 5 average rating, 220 reviews

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 2 min walk from King's Arms, Award winning Pub. 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

24–31 Jul

€ 129 per night

Guest favourite

Apartment in Gretton

4.97 out of 5 average rating, 289 reviews

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.

22–29 May

€ 83 per night

Superhost

Home in Rutland

4.8 out of 5 average rating, 141 reviews

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

10–17 Mar

€ 102 per night

Guest favourite

Farm stay in Rutland

4.93 out of 5 average rating, 123 reviews

The Old Stables Retreat, Northfield Farm

Quiet, romantic retreat on small family-run working farm w. rare & native breed cattle & sheep. Fascinating place to learn about food & the countryside. Great place to stay & explore one of England's most lovely countryside areas. Farm shop, open for 20 + yrs, sells a wide range of home grown & home butchered meats & local flour, beers, ready meals & pies. Nr. Rutland Water, & Melton Mowbray, of pie fame, Stamford & Leicester. Great pubs abound, as do walks & entertainment of every kind.

13–20 Aug

€ 135 per night

Superhost

Tiny home in Empingham

4.83 out of 5 average rating, 187 reviews

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, shop and pub. The local area has lots of pubs, cafes and shops. A perfect place to be able to enjoy and explore the county of Rutland.

21–28 Jun

€ 116 per night

Guest favourite

Cottage in Rutland

4.96 out of 5 average rating, 118 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

29 Sep – 6 Oct

€ 312 per night

Guest favourite

Apartment in Uppingham

4.92 out of 5 average rating, 118 reviews

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.

12–19 Jun

€ 98 per night

Guest favourite

Flat in Rutland

4.89 out of 5 average rating, 205 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 couples.

10–17 Dec

€ 157 per night

Guest favourite

Home in Uppingham

4.93 out of 5 average rating, 105 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.

23–30 Sep

€ 143 per night

Guest favourite

Townhouse in Rutland

4.95 out of 5 average rating, 248 reviews

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.

30 Oct – 6 Nov

€ 153 per night

Superhost

Guest suite in Rutland

4.8 out of 5 average rating, 115 reviews

Self-contained Studio annexe in Oakham.

Lovely studio, has its own entrance at the front of house and access to back garden through the patio doors in the room. Recently added a shower in the studio so it is completely self contained now. Small kitchen area with sink and a full size fridge, and a washing machine if needed. There is one double bed in the studio, but also a self inflating single air bed with bedding if required. Smoking is not allowed throughout the property .

10–17 Oct

€ 75 per night

Guest favourite

Home in Manton

4.96 out of 5 average rating, 167 reviews

Oak Tree Annexe

This unique place has a style all of its own, set in a secluded and secure garden. The house is in one of Rutland’s most desirable villages and on the cycle route around the water offering easy access to all the activities that the area offers. The historic towns of Oakham and Uppingham are just a very short drive from the property. The village pub, which serves food, is a 2 minute walk and is very popular with visitors to the area.

22 Feb – 1 Mar

€ 120 per night