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Uppingham

Uppingham, Oakham, UK

Uppingham

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Uppingham

Step into Uppingham, where cobbled streets are lined with charming boutiques and historic charm awaits at every turn! Indulge in scrumptious treats at local cafés, soak in the stunning architecture, and explore picturesque countryside trails. Don’t miss the vibrant market square—perfect for people-watching! Uppingham is a delightful treasure just begging to be explored!

Recommendations

Landmark

Uppingham School

Culture5/5

Church of St Peter and St Paul, Uppingham

Shop5/5

Mark Gilbert Antiques

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Landmark

Uppingham First

Shop3.8/5

StitchUpp

Landmark

Tod's Piece Playground

Landmark4.5/5

Oakham Castle

Welcome to Oakham Castle, a charming historic site in the heart of Oakham. Explore the well-preserved Great Hall with its stunning Norman architecture. Don't miss the intricate horseshoes on display, a symbol of the town's history. Afterward, stroll through the picturesque Castle Grounds and soak in the beauty of this lovely market town.

Culture4.5/5

Rutland County Museum

Explore Rutland County Museum for a delightful trip through Oakham's history. From old maps and relics to interactive exhibits, this charming museum on Catmos Street is a must-visit for history buffs and curious travelers alike. Don't miss out on their various events and workshops for a fun-filled educational experience!

Culture4.7/5

All Saints Church : Oakham

Landmark4.4/5

The Butter Cross

Outdoor4.5/5

Cutts Close Park

Culture4.7/5

Normanton Church

Landmark4.6/5

Lyndon Visitor Centre & Nature Reserve

Landmark4.8/5

Fort Henry

Outdoor4.5/5

Rutland Watersports

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Landmark

Empingham Reservoir.

Cafe$$$4.4/5

Don Paddy's

Eat$$$4.6/5

Hambleton Bakery

Shop5/5

The Uppingham Cellar

Eat$$$4.9/5

Hitchen's Barn

Stays

Stay5/5

Cuckoo Barn

Stay4.65/5

Broccoli Bottom

Nestled in the charming village of Manton, Broccoli Bottom is a cozy retreat surrounded by rolling green hills. The vibrant Wing Rd leads you to this hidden gem, where you'll find quaint cottages, friendly locals, and delicious farm-to-table dining options. Don't forget to snap a photo of the beautiful oak trees lining the streets!

Stay4.45/5

The Corner House | Self Catering Accommodation Holiday Let

Stay4.45/5

The White Lion Inn

Looking for a cozy spot to rest your weary travelers' feet? Swing by The White Lion Inn in Whissendine, Oakham! This charming village pub on Main St is the perfect place to unwind with a pint and some hearty pub grub. With its welcoming atmosphere and friendly locals, you'll feel right at home in no time!

Stay4.45/5

The Falcon Hotel

Stay4.3/5

Wisteria Hotel

Tucked away on Catmos Street in Oakham, Wisteria Hotel is a cozy retreat for weary travelers. With its charming facade and comfortable rooms, this quaint spot is the perfect place to unwind after a day of exploring the beautiful countryside. Don't forget to grab a bite at their on-site restaurant for a taste of local flavors!

Stay$$$4.2/5

The Admiral Hornblower

Ahoy mateys! The Admiral Hornblower in Oakham is a charming pub on High St with a nautical theme. Enjoy hearty pub grub, local ales, and cozy ambiance. Don't miss their live music nights and quiz evenings. Set sail for a great time at this hidden gem in the heart of Oakham!

Stay4.15/5

Rutland Retreats

Stay$$$4.15/5

The Coach House Inn

Stay4.15/5

The Barnsdale Hotel, Rutland

Stay4.15/5

The Crown

Stay4.05/5

The George Inn Oakham

Located in the heart of Oakham, The George Inn is the perfect spot for weary travelers to kick back and relax. With a charming atmosphere, friendly staff, and delicious pub grub, this historic inn is a must-visit. Enjoy a pint of local ale in the cozy bar or sit outside and soak up the quaint market town vibes. Cheers to that!

Stay3.9/5

The Walled Garden Holiday Cottage

Stay3.9/5

Rutland Hall Hotel & Spa

Stay5/5

Rutland Rural Retreats

Stay4.8/5

Hambleton Hall

Welcome to Hambleton Hall, located on Ketton Road in the charming town of Oakham, UK. This elegant countryside retreat offers a perfect blend of luxury, relaxation, and mouthwatering dining experiences. With its picturesque views of Rutland Water, delightful gardens, and elegant rooms, this is the perfect spot to unwind and indulge in some well-deserved pampering. A true haven for the discerning traveler!

Things To Do
Provided byViator

5/5

Oakham Private Historical Pub Walking Tour With Free Drinks!

Our Private Oakham Pub Tour isn’t just a pub tour but also visits some of the oldest and most characterful parts of the market town of Oakham and we will see castles, churches, market squares, and all sorts of other history along the way.  A drink for each person in each pub is included in the tour price though of course, soft and sometimes hot drinks are available if preferred. We normally meet outside Oakham Railway Station which is easy for day-trippers from London (also Nottingham, Peterborough, and Leicester) but this tour is also perfect for anyone staying in one of the lovely hotels in Rutland, all just a short taxi ride away.  If you’re staying in Oakham itself, I can meet you at your hotel.

$103.14
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5/5
1 h

Revival Rum Distillery Tour: Tasting and branded glass Included

Step into the world of craft rum with a fully immersive distillery tour at Revival Rum. Led by master distiller James Singlehurst, discover the unique processes behind the creation of award-winning rums. Engage in a tantalizing tasting experience directly from the barrels and enjoy a selection of Revival's finest rums. Each tour participant walks away with a complimentary revival Rum Glass, making this a must-try for rum enthusiasts. - Guided tour by master distiller James Singlehurst - Taste directly from the barrels and sample various rums - Ideal for rum lovers and those curious about distilling processes

$79.76
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5/5

Oakham Private Walking Tour

The history of Oakham goes back over a thousand years with people living here much earlier too. Oakham is a beautiful vibrant market town which somehow manages to be wonderfully quiet compared to the noisy chaos of London. It makes for a great day out or even long weekend away. Our special private walking tour is the best way to either see it all or get your bearings for a longer stay. Our Private Walking Tour is just for you and will explore all the nooks and crannies of this beautiful market town, the county town of Rutland. See the unique castle set amongst its old walls and beautiful park with old bandstand. Admire the fabulous old church and check out the old Stocks in the Buttermarket amongst much more besides. Oakham and Rutland are known for being great for foodies and there is lots to see and buy. It's a private tour so runs when you want it and at whatever pace you like. Please note Oakham is a small market town, museum & castle interior closed Sundays & Tuesdays.

$34.38
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5/5
7 h

Private Tour: Pilgrimage to Walsingham Tour

This private tour and pilgrimage takes you to the holy village of Walsingham to visit both the Roman Catholic and Anglican shrines and other related sites. You’ll explore the abbey ruins and the village, and have time to shop for religious items. Take a pilgrimage to the holy village of Walsingham, located in the county of Norfolk, a world away from the hustle and bustle of London. Travel by private car through the Thetford Forest on the way to Walsingham on this full-day guided tour and pilgrimage. The tour lasts around 6-7 hours including travel time.

$428.60
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5/5

Stamford and Burghley House Private Tour

Stamford is a real hidden jewel of England. It has unique mix of history and fabulous Georgian architecture along with some terrific old shopping streets. Maybe that is why Sir Walter Scott declared Stamford to be “the finest stone town in England”. With over 600 listed buildings of gorgeous limestone including five of the most spectacular medieval churches anyway it is perhaps not a surprise that it is often voted amongst the best places to live and also home to best high street in Britain.  Next to Burghley House, known around the world for its Horsetrials and depicted in all sorts of big TV and cinema shows. Burghley is one of the largest & grandest surviving houses of the 16thC & amongst the very finest examples of the great Elizabethan houses.  We will explore all over the house in the service areas & upstairs for all the magnificent rooms and corridors all richly decorated with fabulous works of art. Finally we can explore the gardens and landscaped estate.

$165.02
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5/5

Roaming Rutland Private Tour

Rutland is England’s smallest and some might say its prettiest county. One thing is for certain, Rutland lives up to its motto, Multum in Parvo or ‘much in little’. In this private tour you will just want this beautiful little place has to offer. Explore the market towns and rolling countryside and its famous Rutland Water. Visit castles, churches and walk down beautiful streets and lanes. Perhaps treat yourself to something nice. Rutland is well known for being foodie paradise (Pork Pie and Stilton for me if you're asking). One thing you won’t help but notice is the beautiful rolling countryside in Rutland which combined with its perfect picturesque villages has been labelled the new Cotswolds we will find out why. This is a private tour just for you by car with a certain level of walking at each spot. I know where I'd like to take you but it's all easy going and we can go with the flow, wherever that takes us. There truly is Much In Little.

$123.77
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5/5
6 h

Oakham and Stamford Private Walking Tour

This private walking tour explores two of the most beautiful little market towns in Britain that are only a few miles apart but which are entirely different in how they look and feel. We will spend around 3 hours in lovely Oakham before hopping 10 minutes on the train (or by car if you prefer) to Stamford. Oakham is the county town of Rutland. Our smallest county with gorgeous countryside all around and with a well-deserved reputation for its quality food and drink and artisan shops. Oakham also has a unique Great Hall in the castle, old buttercross & market & much more. Stamford is perhaps the finest Georgian-era town in Britain. You might not have been there before but you’ll likely recognise it from its many appearances onscreen. Stamford’s narrow alleyways and hidden courtyards are home to all manner of specialty shops, fine jewelers & designer boutiques. It also has a Friday Market and a buzzing High Street. Not forgetting the great history and architecture. It's heaven!

$123.77
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5/5

Sydney Gems Private Tour & Pick up & Drop off

Experience the breathtaking, panoramic beauty of Sydney on a private tour with your personal guide. Escape the crowds in your own luxury SUV as you visit iconic landmarks and hidden gems. Your journey will take you through Sydney’s renowned suburbs, tailored to your unique interests, ensuring every moment is meaningful. At Kookaburra Sydney Tours, we believe it’s the memorable experiences and connections that enrich our lives, not just the passage of time. Included: - Private Guide - Private Transportation - Private & clean vehicle

$251.70
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4.9/5
1 h 30 mins

Stamford Town Guided Tours

Join us on a 90 minute guided tour of this Lincolnshire gem. We will deliver an entertaining and informative narration of the architecture, characters and legends of one of the finest stone towns in England. Stamford has preserved a multitude of Georgian buildings built on a medieval base with Tudor and Victorian interludes. The town has a vibrant history, much of which is still visible in the 600 listed buildings and monuments. We are “The Mayor’s Guides”. Starting at the Town Hall, our tour of this ancient town will bring alive the story of Stamford with tales of Georgian elegance, dubious politics, tragic romance and much more! Afterwards, perhaps you can enjoy the many pubs, restaurants or independent shops that make Stamford such a great place to visit.

$14.44
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Melton Mowbray Private Walking Tour

Step back in time and uncover the fascinating past of one of England’s most historic market towns with our Melton Mowbray Historical Walking Tour. Famous for pork pies and Stilton cheese, Melton’s rich heritage goes far beyond its culinary fame. Join us as we stroll through centuries of history – from medieval market squares and ancient churches to grand Georgian architecture and the town’s vital role in the hunting and equestrian traditions of England’s elite. Hear tales of royalty, rebels, monks, and merchants as we bring to life the characters and events that shaped this charming Leicestershire gem. Explore the ancient Church of St Mary, one of the finest parish churches in the country Learn the true origins of the world-famous Melton Mowbray Pork Pie Walk in the footsteps of Victorian aristocrats and Georgian gentlemen Hear local legends & historical curiosities that bring the town’s past vividly to life Perfect for history buffs, families, and curious travellers of all ages.

$82.51
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Stamford and Oakham Private Tour

This private walking tour explores two of the most beautiful little market towns in Britain that are only a few miles apart but which are entirely different in how they look and feel. We will spend around 3 hours in lovely Stamford before hopping 10 minutes on the train (or by car if you prefer) to Stamford. Stamford is perhaps the finest Georgian-era town in Britain. You might not have been there before but you’ll likely recognise it from its many appearances onscreen. Stamford’s narrow alleyways and hidden courtyards are home to all manner of specialty shops, fine jewelers & designer boutiques. It also has a Friday Market and a buzzing High Street. Not forgetting the great history and architecture. It's heaven! Oakham is the county town of Rutland. Our smallest county with gorgeous countryside all around and with a well-deserved reputation for its quality food and drink and artisan shops. Oakham also has a unique Great Hall in the castle, old buttercross & market & much more.

$123.77
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Peterborough and Stamford Private Guided Tour

This tour is great for anyone making a day trip from London. We would meet you outside Peterborough Station (45 minutes from London) or indeed from anywhere else you might be travelling.  A few minutes away is the wonderful old Guildhall. Built originally in 1671 it has served as both a market and a townhall. A farmers market is still held here regularly along with many over events in the square. A short stroll away is the really rather wonderful Peterborough Cathedral which we shall explore inside. We can then get the train a short distance to either the beautiful Georgian Town of Stamford or the county town of Rutland, Oakham or both of them for a full day out. Pick which option is best for you.

$144.40
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8 h

Oakham's Horrible History Private Tour - 'Orrible gore & ghosts!

For such a beautiful picturesque market town, Oakham is an unexpectedly dark and grim history that most people are oblivious to today despite. On this tour we will learn about some of the actual dark history of Oakham, the people who lived and died here... one man who lived, died and lived again! Oakham has Britains oldest court, the only operational gallows in the country and a fantastic set of Stocks in market square. We will visit various spots of executions and see the evidence that remains today. Murders, ghosts, corporal punishments and much more. It's a private tour so runs at a time that works for you but to see the Oakham Castle Court and nearby functional gallows we have to be underway by 3pm.

$82.51
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Private Half Day Stamford Pub Tour With Free Drinks

The beautiful town of Stamford is on the old coaching route between London, York, Newcastle and Edinburgh and as such is the natural home for some wonderfully characterful pubs and inns that would have been a hive of activity in days gone by. Today Stamford is said to be the finest stone city in Britain, there are less horse and carts and more ambling visitors and shoppers exploring all the nooks and crannies. The pub tour is a great alternative way to see this marvelous old town whilst learning its history as we visit some of its most historic old pubs with a drink included in each one (drinks not compulsory).

$159.52
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