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
"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...
"Stables Cottage , Tilton On The Hill" is a 3 bed holiday Apartment sleeping up to 6 guests in Leicestershire. Positioned in a tranquil and totally private setting, Stables Cottage is a beautifully converted former stable yard located on a working farm, set in 80 acres of grassland and woodland. The open-plan living space includes a large bespoke...
"9 Rectory Lane" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland. Oakham is the delightful county town of Rutland, and is a great place to visit and spend a holiday. It is filled with pretty stone and thatched buildings and offers something for everyone, it's a great family holiday destination. The town...
"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...
"Rowan Lodge" is a 2 bed holiday Lodge sleeping up to 4 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...
"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...
"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...
"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....
"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...
"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...
"Carrot Cottage - UK32609" is a 2 bed holiday Cottage sleeping up to 6 guests in Rutland. With multiple activities and sites on the doorstep, this is a great place to stay for couples, families and groups.. 2 steps to entrance. All on the Ground Floor: Open plan living space. Living...
"Hambleton" 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. The Fox and Hounds public house overlooks the tree-planted green, and it serveds delicious food and drink. Oakham is the nearest town, boasting a range of shops, as well as pubs,...
"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...
"Doctors Lane" is a 3 bed holiday Cottage sleeping up to 5 guests in Leicestershire. A comfortable and well presented three bedroom house close to the centre of Melton Mowbray.. 2 steps to entrance. Ground Floor: Living room: Freeview Smart TV Dining...
"Parsnip Place - UK32606" is a 1 bed holiday Cottage sleeping up to 2 guests in Rutland. A cute and comfortable stay awaits you in this idyllic countryside location.. All on the Ground Floor: Open plan living space. Living area: Freeview TV Dining...
"The Stables" is a 2 bed holiday Cottage sleeping up to 4 guests in Leicestershire. A lovely modern holiday home set within a converted stable block, just a short walking distance to the town centre.. Ground Floor: Living/dining room: Freeview Smart TV Kitchen/dining room:...
"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...
"Bakers Retreat" is a 3 bed holiday Cottage sleeping up to 6 guests in Rutland. Think quintessentially English "chocolate box" cottage and you’ll find this is it! A superb thatched cottage in a beautiful and peaceful village.. Ground Floor: Living room: (1 Step), Smart TV, Open...
"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...
"Mange-Tout Maison - UK32607" is a 2 bed holiday Cottage sleeping up to 4 guests in Rutland. A perfect place to have a restful stay surrounded by beautiful countryside.. 14 steps to entrance. All on the First Floor: Open plan living space. Living area: Freeview TV Dining...
"Porter's Barn" is a 1 bed holiday Cottage sleeping up to 2 guests in Lincolnshire. Ideally located near Castle Bytham, Stamford, and Rutland Water, it’s perfect for relaxing breaks, scenic walks, cycling, and exploring local pubs and market towns.. 2 steps to entrance. All on the Ground Floor:...
"Jack's Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Lincolnshire. The perfect choice for a couple or small family, Jack’s Cottage offers cosy, comfortable accommodation in a lovely rural location.. Ground Floor: Living room: 40" Smart TV, Open Fire, Sofa Bed (Double)...
"Brooke" 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...
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.
