Holiday rentals in Oakham

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Top-rated holiday rentals in Oakham

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Top guest favourite

Townhouse in Manton

4.99 out of 5 average rating, 146 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

Apartment in Tilton on the Hill

4.88 out of 5 average rating, 139 reviews

The Hayloft: Popular Hideaway - Sleeps 3.

After our storming success for 6 years with our cosy Hayloft Apartment, we have totally refitted the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking [Now with EV Charging] a private patio for sunny breakfasts, lunches or sundowners. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details. The Welcome pack's a big hit.

Guest favourite

Cottage in Rutland

4.96 out of 5 average rating, 140 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, 140 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.

Top guest favourite

Home in Manton

4.96 out of 5 average rating, 307 reviews

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.

Guest favourite

Cottage in Wing

4.85 out of 5 average rating, 285 reviews

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.

Top guest favourite

Home in Uppingham

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.

Guest favourite

Cottage in Wing

4.89 out of 5 average rating, 265 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 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 Rutland

4.95 out of 5 average rating, 311 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

4.79 out of 5 average rating, 214 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 .

Top guest favourite

Barn in Whissendine

4.99 out of 5 average rating, 138 reviews

Beautiful Conversion in Rutland Countryside

Come and stay in our lovingly converted barn in the middle of the Rutland countryside. Perfect for a quiet get-away with lots of walking and cycling from the doorstep. Set in a 3 acre plot of our family home, you will have access to a private garden at the rear of the property plus our orchard should you wish to bring 1 small - medium sized dog with you. Unfortunately, the property is not suited to large dogs.

Guest favourite

Cottage in Uppingham

4.91 out of 5 average rating, 325 reviews

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.