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
"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...
"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...
"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...
"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...
"The Cuckoo's Rest" is a 2 bed holiday Apartment 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...
"Chelsea House" is a 4 bed holiday Cottage sleeping up to 8 guests in Leicestershire. Melton Mowbray is a stunning town found in Leicestershire, famous for it's tasty pies and butchers. Perfect for beer lovers, Melton Mowbray boasts an array of brewery's and historic pubs, including the Ann of Cleves, known for being an old home...
"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,...
"Elm Tree 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...
"The Folkesworth" is a 4 bed holiday Lodge sleeping up to 8 guests in Peterborough. King's Lynn is a historic, medieval port dating back to the 12th century, situated on the River Great Ouse. A treasure trove for history lovers, the town boasts grand merchant houses, art galleries and museums, and the Custom House, built by...
"The Folkesworth (Pet)" is a 4 bed holiday Lodge sleeping up to 8 guests in Peterborough. King's Lynn is a historic, medieval port dating back to the 12th century, situated on the River Great Ouse. A treasure trove for history lovers, the town boasts grand merchant houses, art galleries and museums, and the Custom House, built by...
"The Alwalton (Pet)" is a 4 bed holiday Lodge sleeping up to 8 guests in Peterborough. King's Lynn is a historic, medieval port dating back to the 12th century, situated on the River Great Ouse. A treasure trove for history lovers, the town boasts grand merchant houses, art galleries and museums, and the Custom House, built by...
"The Kingfisher Falls" is a 3 bed holiday Cottage sleeping up to 6 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...
"Moorhen - Exton Park, Exton" is a 3 bed holiday Cottage sleeping up to 6 guests in Rutland. Set within the historic walled garden of Exton Park in Rutland, Moorhrn is one of six peaceful safari tents surrounded by open countryside, mature trees and the quiet charm of the estate. Hidden within this beautiful private setting, it feels...
"Coot - Exton Park, Exton" is a 3 bed holiday Cottage sleeping up to 6 guests in Rutland. Each tent at our Lantern & Larks locations, accommodates six guests across three bedrooms. There is one king size room, one twin room and one bunk bedroom. Inside, there is an open plan living area with a spacious kitchen featuring a double...
"Cygnet - Exton Park, Exton" is a 3 bed holiday Cottage sleeping up to 6 guests in Rutland. Each tent at our Lantern & Larks locations, accommodates six guests across three bedrooms. There is one king size room, one twin room and one bunk bedroom. Inside, there is an open plan living area with a spacious kitchen featuring a double...
"Kite - Exton Park, Exton" is a 3 bed holiday Cottage sleeping up to 6 guests in Rutland. Each tent at our Lantern & Larks locations, accommodates six guests across three bedrooms. There is one king size room, one twin room and one bunk bedroom. Inside, there is an open plan living area with a spacious kitchen featuring a double...
"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...
"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...
"Teal - Exton Park, Exton" is a 3 bed holiday Cottage sleeping up to 6 guests in Rutland. Each tent at our Lantern & Larks locations, accommodates six guests across three bedrooms. There is one king size room, one twin room and one bunk bedroom. Inside, there is an open plan living area with a spacious kitchen featuring a double...
"Hill View" is a 5 bed holiday Cottage sleeping up to 20 guests in Lincolnshire. Hill View is everything you, your family and your friends want in a group self-catering property, including accommodation for up to 19 people in five bedrooms. The gorgeous house is on the Rutland Border, only six miles from...
"Manor View" is a 3 bed holiday Cottage sleeping up to 7 guests in Rutland. The village of Edith Weston stands on the south shore of Rutland Water. The unusual name recalls the history of the village, which was given by Edward the Confessor to his queen, Edith. The village has a shop, pub and Post Office. Further...
"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...
"Church View" is a 1 bed holiday Lodge sleeping up to 2 guests in Rutland. Greetham is a rural village nestled in the beautiful county of Rutland, close to Rutland Water Nature Reserve. It boasts two pubs, a village shop and the Greetham Valley Golf Club. Nearby, Oakham has a good range of shops, restaurants and bars...
"Swan & Robin" is a 1 bed holiday Hotel sleeping up to 1 guests in Leicestershire.
Popular towns in and around Leicestershire:
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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.
