Tucked away between the Norfolk Coast and rolling Leicestershire countryside, Rutland is almost England’s best-kept holiday secret. Oakham is a gorgeous medieval town packed with beautiful sights, thriving businesses and centuries of history. The picturesque county is the smallest in England but what it lacks in stature it more than compensates for in appeal making its motto, Multum in Parvo (Much in Little) perfectly fitting. Our holiday cottages to rent in Oakham are ideal for couples, families and friends who want to spend time together enjoying the plentiful and varied delights of this postcard-perfect town and the surrounding countryside of Rutland. Read more
This dog-friendly holiday cottage is ideal for families, couples, or friends seeking a peaceful getaway. With comfortable accommodations for up to five guests, including a delightful garden and three elegant bedrooms, it's perfect for relaxation. Enjoy nearby attractions like Rutland Water, Stretton Lakes for fishing, and the vibrant Oakham market. Unwind at the welcoming Sun Inn and explore local treasures like Burghley House. Victory Cottage offers 5-star Gold standard luxury for an unforgettable holiday in the heart of beautiful Rutland. Tourist board rating: 5 Star Gold
Clover at Stretton Lakes offers Five Star Gold self-catering. Just for two this lovely log cabin is perfectly set overlooking fishing lakes surrounded by woodland with its own private hot tub and indoor sauna providing the ultimate in relaxation for couples wanting a romantic retreat! Tourist board rating: 5 Star Gold
Waterlily offers 5 Star Gold self-catering for two, perfectly set overlooking Stretton Lakes, surrounded by woodland with its own private hot tub and indoor sauna. The ultimate in relaxation for couples wanting some peace and tranquility and a romantic break! Tourist board rating: 5 Star Gold
A Five Star Gold log cabin for two sitting in a tranquil position in the small county of Rutland. Overlooking the fishing lakes and surrounded by woodland, Poppy offers a high standard of holiday accommodation with its own private hot tub as well as an indoor sauna providing the ultimate in relaxation for couples wanting a romantic retreat! Tourist board rating: 5 Star Gold
Stretton Lakes provides a tranquil haven to escape the pressures of every day life with a choice of six luxury log cabins for a self-catering holiday. Sitting in the county of Rutland, the cabins overlook the fishing lakes and are encapsulated by woods and each has its own private hot tub providing the ultimate in relaxation! Tourist board rating: 4 Star Gold
A 4 Star Gold log cabin which is perfectly set overlooking the fishing lakes surrounded by woodland. This welcoming self-catering holiday rental has its own private hot tub offering the ultimate in relaxation! Sitting in England's smallest county, what Rutland lacks in size, it makes up for in beauty with one of Europe's largest man-made reservoirs, perfect for outdoor enthusiasts and water lovers. Tourist board rating: 4 Star Gold
Bluebell is a luxurious log cabin nestling in a peaceful haven amongst woodland with its own hot tub in the county of Rutland. Beautifully presented to Four Star Gold standard, the self-catering lodge is surrounded by farmland abundant with wildlife with lovely views over the fishing lakes. All the right ingredients for a relaxing holiday. Tourist board rating: 4 Star Gold
"The Oak Room - Windmill Country Retreats" is a 1 bed holiday Apartment sleeping up to 2 guests in Leicestershire. Buckminster is a quaint, countryside village resting between Grantham and Leicester. The village is known for its picturesque, autumnal trees surrounding Buckminster Park, and offers a selection of attractions and eateries including the...
"Rectory Cottage, Tinwell, near Stamford" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland. This exquisitely designed luxury cottage in Tinwell near Stamford is a dreamy abode for lovebirds looking for a romantic break in 'The best place to live in the Midlands' (as voted by the Sunday Times 2021). Rectory Cottage started life humbly...
"1 Bed Cottage in Oakham" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 Bedroom - king-size - 1 Shower room - Electric oven and induction hob, microwave, fridge with ice compartment, coffee machine and...
"Bee Hive" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Edith Weston is a pretty little village with lovely stone cottages, a pretty little church with a stained glass window inside, as well as a village shop. Post Office and pub. The nearby Rutland Water offers something for all and includes a...
"Badger's Burrow" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Edith Weston is a pretty little village with lovely stone cottages, a pretty little church with a stained glass window inside, as well as a village shop. Post Office and pub. The nearby Rutland Water offers something for all and includes a...
"Squirrel's Nest" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Edith Weston is a pretty little village with lovely stone cottages, a pretty little church with a stained glass window inside, as well as a village shop. Post Office and pub. The nearby Rutland Water offers something for all and includes a...
"Otter's View" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Edith Weston is a pretty little village with lovely stone cottages, a pretty little church with a stained glass window inside, as well as a village shop. Post Office and pub. The nearby Rutland Water offers something for all and includes a...
"1 Bed Cottage in Stamford" is a 1 bed holiday Cottage sleeping up to 2 guests in Lincolnshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 bedroom - king-size - 1 bathroom – bath, separate shower and WC - Electric oven and hob, dishwasher, fridge and washing machine - Travel...
"Burley" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Exton is a village set in the East Midlands county of Rutland. The Fox and Hounds public house overlooks the tree-planted green, offering cosy winter evenings around the fireplace and lazy summer days out in the beer garden. Oakham is the...
"Halliday’s Cottages - The Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland. The pretty village of Cottingham lies in the East Riding of Yorkshire, to the north of Kingston upon Hull and only a few miles from the pretty market town of Beverley. Cottingham has a small high street with a selection of shops, pubs,...
"Glossoms Lodge" is a 1 bed holiday Cottage sleeping up to 2 guests in Leicestershire. Surrounded by the beautiful Leicestershire countryside is this spacious one bedroom property, perfectly positioned for a wealth of areas and attractions.. 2 steps to entrance. All on the Ground Floor: Living...
"The Stables" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland. The views from this property are simply stunning, come and see for yourself!. 2 steps to entrance. Ground Floor: Open plan living space. Living area: Freeview Smart TV Dining...
"Orchard Loft" is a 1 bed holiday Apartment sleeping up to 2 guests in Rutland. A fabulous and spacious loft apartment overlooking the orchard, fields and countryside beyond. A great place to get away for countryside walks, cycling and seeing the delights Rutland has to offer.. Ground Floor:...
"Fennel Folly - UK32608" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland. Beautiful far reaching views over the countryside from the balcony of this fabulous well equipped apartment.. 14 steps to entrance. All on the First Floor: Open plan living space. Living...
"Little Launde Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Leicester. Historically founded in Saxon times, Tilton on the Hill was at the crossroads of old paths between Leicester, Oakham, Market Harborough and Melton Mowbray, offering great access to markets and towns. Nowadays the village is a pretty English...
"Tickencote" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Exton is set in the East Midlands county of Rutland. The Fox and Hounds public house overlooks the tree-planted green in the centre of the village. Oakham is the nearest town, boasting many pubs, bars and eateries, as well as shops. There is...
"Stables Annex" is a 2 bed holiday Cottage sleeping up to 4 guests in Leicestershire. The town of Melton Mowbray is set in Leicestershire. Well known for its popular pies, this well-loved town is set just 19 miles from Leicester and 20 miles from Nottingham. With a host of cafes, butchers’, shops and pubs in this delightful...
"Rabbit Hole" is a 2 bed holiday Lodge sleeping up to 6 guests in Rutland. This wonderful stone-built Georgian market town is thought to be one of the finest stone towns in England. Famous for its use as Meryton in the 2005 Pride & Prejudice film, the town offers an excellent variety of independent shops,...
"Redcot Gardens" is a 2 bed holiday Cottage sleeping up to 3 guests in Lincolnshire. A beautiful and stylish, modern house perfect for a family holiday, and located in the historic market town of Stamford.. Ground Floor: Living room: Freeview TV Kitchen/dining room:...
"Clipsham" is a 3 bed holiday Lodge sleeping up to 6 guests in Rutland. This village is set in the East Midlands county of Rutland. The Fox and Hounds public house overlooks the tree-planted green, offering cosy winter evenings around the fireplace. Oakham is the nearest town, boasting a combination of stone and...
"4 Bed Cottage in Oakham" is a 4 bed holiday Cottage sleeping up to 6 guests in Rutland. Additional information and rules. Please enquire if you wish to bring more than 1 dog - Sleeps 6+1 ( Maximum of 7 guests) - 4 bedrooms – 1 king-size, 1 double, 1 twin bedroom and 1 single - 2 bathrooms – 1 bathroom with bath and...
"Regent’s Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Leicestershire. The town of Melton Mowbray is set in Leicestershire. Well known for its popular pies, this well-loved town is set just 19 miles from Leicester and 20 miles from Nottingham. With a host of cafes, butchers’, shops and pubs in this delightful...
"Glaston" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Exton is a village set in the East Midlands county of Rutland, with The Fox and Hounds public house overlooking the tree-planted green. Oakham is the nearest town, boasting a combination of stone and thatched buildings, along with a range of...
"The Walnut Room - Windmill Country Retreats" is a 1 bed holiday Apartment sleeping up to 4 guests in Leicestershire. Buckminster is a quaint, countryside village resting between Grantham and Leicester. The village is known for its picturesque, autumnal trees surrounding Buckminster Park, and offers a selection of attractions and eateries including the...
Popular towns in and around Leicestershire:
Appleby MagnaBruntingthorpeFleckneyGreat GlenLeicesterMarket BosworthMarket HarboroughMelton MowbrayNottinghamOakhamRugbyRutlandShearsbySearch within Eastern Central England
A Town Bursting with History and Charm - No one who visits Oakham can deny the beauty of the landscape. The town is saturated in charm, and a fantastic way to explore it is on foot. Start your tour with a visit to the Rutland County Museum on Catmos Street. Entry is free, and the exhibits cover the region’s history from the Jurassic period to medieval times and beyond. Stroll around town to see the recently-restored Oakham Castle as well as the buildings of Oakham School. Markets are held every Wednesday and Saturday in the pedestrianised Market Square, and there is a Farmers’ Market on the third Saturday of the month on Gaol Street. Even if you miss the market day, there is a fantastic choice of places serving seasonal local produce, including Otters Smokehouse & Deli where you can dine in or take away local cheese, charcuterie and ale to enjoy on a picnic or back at the holiday cottage.
A Delight to Explore - The area around Oakham is a pleasure to explore, especially on foot or by bicycle. Fantastic footpaths lead to views so serene and beautiful that you may find yourself pondering the feasibility of a move to the Rutland countryside. Rutland is so small that its circumference measures only 65 miles with the Rutland Round footpath covering the distance. Other long-distance trails in Rutland include the 64-mile Melton Round and the 80-mile long Uppingham Round, both of which pass within easy reach of Oakham and give stunning views. Closer to home, the Oakham Heritage Trail is a favourite with locals and visitors.
If you prefer to sightsee from the comfort of your car then consider driving along the scenic Rutland Water Trail, Bishop’s Eye Trail, Forgotten Rutland Trail and the curiously-named Lost and Gone Trail.
Rutland Water, a Holiday Destination in its Own Right - Just outside of Oakham, Rutland Water is an outdoor lover’s paradise. As the biggest constructed lake in England, and one of the largest in Europe, it offers a wealth of opportunities to sail, fish, walk, cycle and birdwatch, among other fun activities. The lake sits in 3,000 acres of countryside and is a top choice for a family day out.
Multum in Parvo - Despite its size, there is plenty to keep everyone happily occupied on a self-catering cottage holiday in Oakham, no matter what the season. Day trips can include Upphingham, Burghley House, Rockingham Castle, Belvoir Castle, the ancient city of Cambridge, Lincoln Cathedral, Leicester and Grantham.
You will love your time spent in Oakham. The charming town has the captivating sensation of stepping back in time, yet there is nothing backward about it. Being in the Midlands makes it easy to reach from most parts of England, including the South East. Rutland has a full calendar of events that caters to all tastes and includes highlights such as the Rutland Food and Drink Festival and the Burghley Horse Trials. Just as it has for countless other holidaymakers, Oakham could soon become one of your favourite getaway destinations.
