Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- Maple Lodge
- Sycamore Lodge
- Rowan Lodge
- Fairchild’s Barn at Fairchilds
- Waxwing Cottage
- Cherry Tree Lodge
- Poppie’s Shepherd Hut
- Bonnie’s Shepherd Hut
- The Woodshed in Congerstone
- Under Willows
- Hare’s Furrow
- The Cottage At Hall Farm House
- Rose Cottage Empingham
- Big Drift Barn at Fairchilds
- Oak Lodge
- Pine Lodge
- The Copper Pot - Snowford Hill
- Church View
- Buddy
- Pheasant Lodge at Coplow Cabins
- Holly Lodge
- Ash Lodge
- Beech Lodge
- Cedar Lodge
- Reynard’s Retreat at Coplow Cabins
- The Pinfold
- Barn Owl
- Yew Lodge
- Lillie’s Shepherd Hut
- Willow Lodge
Oakham Holiday Cottages
Our collection of Oakham holiday cottages offers you the perfect base to explore Rutland's charming county town. You'll discover historic Oakham Castle with its remarkable Great Hall and unique horseshoe collection! The bustling market square hosts traditional markets twice weekly where local traders sell fresh produce and crafts.
Your stay places you moments from Rutland Water, where families can enjoy cycling the 23-mile perimeter track or trying water sports. Groups and couples will love browsing independent shops along High Street and Mill Street. Many properties feature a hot tub for ultimate relaxation after exploring local pubs and restaurants serving fine Rutland fare.
Visitor Rating
4.3
- Thatched cottage with character
- Private hot tub
- Near Rutland Water
- Four spacious bedrooms
- Enclosed garden for pets
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Visitor Rating
4.8
- Private hot tub
- Peaceful woodland location
- Wildlife watching opportunities
- Modern comfortable interiors
- Close to walking trails
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Visitor Rating
4.6
- Private hot tub
- Peaceful countryside location
- Wildlife spotting opportunities
- Comfortable, well-equipped accommodation
- Pet friendly facilities
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Visitor Rating
4.7
- Hot tub for relaxation
- Peaceful countryside setting
- Comfortable self-catering accommodation
- Private outdoor space
- Modern amenities
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Visitor Rating
4.8
- Lakeside location with stunning views
- Private hot tub on spacious deck
- Close to historic attractions
- Modern, comfortable interior
- Water activities on your doorstep
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Visitor Rating
4.2
- Private hot tub
- Stunning church views
- Peaceful countryside location
- Modern, comfortable interiors
- Perfect romantic getaway
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Visitor Rating
4.7
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Visitor Rating
4.8
- Private hot tub
- Peaceful woodland setting
- King-sized comfortable bed
- Well-equipped modern kitchen
- Walking trails from doorstep
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Visitor Rating
4.9
- Private hot tub
- Pub two doors away
- Immaculately clean property
- Dog-friendly with enclosed patio
- Close to Rutland Water
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Visitor Rating
4.7
- Private hot tub on woodland deck
- Peaceful secluded location
- Modern well-equipped kitchen
- King-size bed with quality linens
- Close to walking trails
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Visitor Rating
4.8
- Private hot tub
- Woodland setting
- Wildlife watching
- Luxury furnishings
- Close to York
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Visitor Rating
4.7
- Private woodland setting
- Luxury hot tub
- Modern, well-equipped interior
- Wildlife watching opportunities
- Close to walking trails
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Visitor Rating
4.8
- Private hot tub
- Peaceful countryside location
- Comfortable well-equipped interior
- Wildlife watching opportunities
- Cosy retreat all year round
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Visitor Rating
4.7
- Private hot tub with woodland views
- Secluded location with wildlife spotting
- Walking trails from the doorstep
- Cosy wood burner for winter evenings
- Dog-friendly accommodation
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Visitor Rating
4.8
- Private hot tub with countryside views
- Peaceful woodland setting
- Wildlife watching opportunities
- Cosy log burner for winter evenings
- Close to historic Lincoln
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Visitor Rating
4.4
- Private hot tub for four
- Stunning countryside views
- Pet friendly accommodation
- Private parking included
- Open plan living space
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Visitor Rating
4.5
- Private hot tub for four
- Countryside views and walks
- Pet friendly at no cost
- Open plan modern living
- Easy access market towns
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Visitor Rating
5
- Private hot tub
- Dog exercise paddock
- Games room for all ages
- Flexible bedroom layouts
- Homemade welcome treats
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Visitor Rating
5
- Private hot tub with views
- Sleeps 11 across four bedrooms
- Ground floor accessibility features
- Enclosed garden and woodland access
- Pet friendly with parking
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Visitor Rating
4
- Private hot tub with countryside views
- Gaming consoles in twin bedrooms
- Working farm with woodland grounds
- Four bedrooms sleeping eleven guests
- Modern barn conversion near Uppingham
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Visitor Rating
4.7
- Private hot tub for four
- Adults-only romantic shepherd's hut
- Beautiful landscaped countryside gardens
- Walking distance to local pub
- Modern amenities with Smart TV
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Visitor Rating
4.4
- Private hot tub for seven
- Four ensuite bedrooms available
- Open plan living space
- Parking for six cars
- Rural Leicestershire countryside location
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Visitor Rating
4.8
- Private wood-fired hot tub
- On-site pub dining
- Working farm location
- Pet-friendly accommodation
- Leicester city access
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Visitor Rating
4.3
- Wood-fired hot tub for two
- Working farm with lake walks
- On-site pub serving local food
- Pet-friendly with beds provided
- Private shepherd's hut accommodation
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Visitor Rating
4.8
- Private hot tub for six
- Three kingsize bedrooms available
- Working farm countryside location
- Level access ground floor
- Enclosed courtyard with furniture
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Visitor Rating
4.9
- Wood-fired hot tub
- Stunning lakeside location
- Dog-friendly enclosed garden
- Digital detox retreat
- Luxury king-size bed
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Visitor Rating
4.9
- Secluded countryside location
- Wood-burning hot tub
- Stunning lake views
- Dog-friendly accommodation
- Helpful attentive hosts
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Visitor Rating
4.8
- Private wood-fired hot tub
- Beautiful waterside views
- Dog-friendly with welcome box
- Peaceful countryside location
- Luxury bedding and furnishings
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- Private wood-fired hot tub
- Starlit ceiling above bed
- Adults-only romantic retreat
- Cosy woodburner included
- Vale of Belvoir countryside
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- Lakeside shepherd hut with hot tub
- Adults-only romantic retreat setting
- Uninterrupted lake views from doorstep
- Private wood-fired hot tub
- Star-lit ceiling and wood burner
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Popular towns and villages in and around Oakham