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
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
"Elm Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Greetham is a rural village resting in the county of Rutland not far from the historic town of Oakham and the fantastic Rutland Water. The village enjoys an active community and is home to a village shop, two pubs and Greetham Valley Golf Club....
"Pine Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Tucked away in the rolling countryside, just a short distance from the historic town of Oakham and resting near Rutland Water, is the quaint village of Greetham. Wandering through the village you will find two welcoming pubs, each serving...
"The Old Bakehouse" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland. Barrowden is a conservation village situated on the River Welland in Rutland. The village has a convenience store with coffee shop and also a pub within a short walk. You are close to the Rutland Water reservoir, ideal for those keen on...
"Holly Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. Resting near to Rutland Water and the charming historical town of Oakham, is the quaint village of Greetham, which has everything one could need during their stay including, two delightful pubs, a community centre, a village shop and the...
"Sycamore Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. This rural village is situated in the county of Rutland, some six miles from the town of Oakham. Greetham is close to Rutland Water, hosting many outdoors activities and the village also has two pubs, a village shop and the Greetham Valley Golf...
"Maple Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in Rutland. This rural village is nestled in the beautiful county of Rutland, some six miles from the historic town of Oakham and very close to Rutland Water, an internationally recognised, man-made nature reserve hosting many outdoors activities and...
"Oak Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in Rutland. Greetham village is situated within the county of Rutland, close to the historic town of Oakham and Rutland Water, a man-made nature reserve hosting many outdoors activities and watersports. The village offers two pubs, a village shop and...
"Yew Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in Rutland. The rural village of Greetham is positioned some six miles from the town of Oakham, close to Rutland Water, where you will find many outdoors activities and watersports for all. The village itself has two pubs, a village shop and the Greetham...
"Harley's House" is a 3 bed holiday Lodge sleeping up to 6 guests in Rutland. In the East Midlands region of Rutland, Exton offers a quintessentially English setting, with old stone houses gathered around the village green. The Fox & Hounds public house, a former 17th-century coaching inn brimming with charm,...
"Seaton" is a 3 bed holiday Lodge sleeping up to 6 guests in Rutland. Exton is a village set in the East Midlands county of Rutland. It has The Fox and Hounds public house overlooking the tree-planted green, with the nearest town being Oakham. This town boasts a combination of stone and thatched buildings, a...
"The Croft" is a 1 bed holiday Apartment sleeping up to 2 guests in Rutland.
"Brook Whipper-In Hotel" is a 1 bed holiday Hotel sleeping up to 2 guests in Rutland.
"Barnsdale Lodge" is a 1 bed holiday Hotel sleeping up to 2 guests in Rutland.
"Broccoli Bottom" is a 1 bed holiday BandB sleeping up to 2 guests in Rutland.
"Ash Lodge" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland.
"Church View" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland.
"Bumble Bee" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland.
"Yew Lodge" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland.
"Oakham Hotel" is a 1 bed holiday Hotel sleeping up to 2 guests in Rutland.
"Sycamore Lodge" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland.
"Willow Lodge" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland.
"1 Bed in Rutland Waters 60672" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland.
"Cosy getaway near Rutland Water" is a 1 bed holiday Apartment sleeping up to 2 guests in Rutland.
"Rutland Water Courtyard Rooms" is a 3 bed holiday Hotel sleeping up to 6 guests in Rutland.
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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.
