Vacation rentals in Oakham

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Top-rated vacation rentals in Oakham

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Guest favourite

Cottage in Wing

4.88 out of 5 average rating, 224 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

Guest favourite

Townhouse in Manton

4.99 out of 5 average rating, 106 reviews

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.

Guest favourite

Condo in Gretton

4.97 out of 5 average rating, 297 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.

Guest favourite

Cottage in Rutland

4.95 out of 5 average rating, 120 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, is 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.

Guest favourite

Farm stay in Rutland

4.92 out of 5 average rating, 127 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.

Guest favourite

Cottage in Empingham

5.0 out of 5 average rating, 118 reviews

Primrose Hall Holiday Cottage Rutland

Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, medical centre, hairdressing salon and pub just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

Guest favourite

Condo in Uppingham

4.92 out of 5 average rating, 122 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.

Guest favourite

Cottage in Kibworth Harcourt

4.94 out of 5 average rating, 160 reviews

Willow Cottage

The accommodation was once a barn dating back to 1900. It is a contemporary conversion within the rear garden of the main house. The property incorporates everything needed for a great stay. It is completely private and self-contained. The ground floor consists of an open plan living room/kitchen and is accessed by two large patio doors. A staircase leads to a light and airy bedroom with a king size bed, drawers and a wardrobe. There is an en-suite bathroom with walk-in shower.

Guest favourite

Home in Uppingham

4.94 out of 5 average rating, 109 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.

Guest favourite

Townhouse in Rutland

4.95 out of 5 average rating, 256 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.

Guest favourite

Guest suite in Rutland

4.81 out of 5 average rating, 131 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 .

Guest favourite

Home in Manton

4.96 out of 5 average rating, 182 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.