Holiday Rentals in Oakham

83 available vacation rental offers

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Oakham holiday rentals
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Best Holiday rentals and Airbnb offers in Oakham

Best family friendly Oakham holiday rentals

Among the 83 accommodations in Oakham, here are the 4 best family friendly rentals

Bennett's Cottage - Oakham
9.9 74 reviews

Bennett's Cottage

house, Oakham
Bennett's Cottage is situated in Oakham, a charming market town in the heart of the English countryside, just 20 miles from Leicester and its train station. The property has received excellent ratings for cleanliness, location, and user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom cottage offers 105 square metres of space, comfortably accommodating up to four guests. You'll find a well-equipped kitchen, a peaceful garden, free Wi-Fi, and parking, making it ideal for families and cycling enthusiasts exploring the beautiful surrounding countryside.
2 Bedroom Accommodation In Oakham - Oakham
8.0 4 reviews

2 Bedroom Accommodation In Oakham

cottage, Oakham
This Oakham riverside cottage is situated less than 1km from Oakham Castle and within 5km of Rutland Water Country Park and Rutland Falconry Centre.
Sleeping up to six guests, this two-bedroom property boasts a fully equipped kitchen, private patio, and convenient access to Oakham railway station, all within a family-friendly setting that welcomes pets.
Kings Retreat - Oakham
9.5 50 reviews

Kings Retreat

cottage, Rutland
This charming cottage is located in Oakham, a historic market town in Rutland, just 3 kilometres from Rutland Water. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage offers a spacious living area for up to 6 guests and features a well-equipped kitchen with a dishwasher. Guests can enjoy a private garden, bike hire, and easy access to the town centre, Rutland Water, and the surrounding countryside.
We Stay - Park Cottage - Oakham
9.8 8 reviews

We Stay - Park Cottage

apartment
Park Cottage, a secluded rural retreat in Glaston, Rutland, enjoys breathtaking countryside views and is situated up a private driveway offering tranquility.
This two-bedroom self-catering property sleeps four, boasting a cosy lounge with log burner, well-equipped kitchen, stylish dining area, luxurious bathroom with Bamford toiletries, and a private garden; off-road parking for two vehicles is also available.

Best Oakham holiday rentals with parking

The Reading Room - Oakham
10 47 reviews

The Reading Room

gîte
This secluded vineyard cabin is located a short distance from Uppingham.
This one-bedroom holiday cottage accommodates two guests and offers a book-lined interior, an outdoor bubble bath, and the opportunity to sample handcrafted wine.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Oakham
10 2 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
The Hideout, a first-floor apartment in Oakham, Rutland, offers convenient access to Oakham Castle and the Rutland County Museum, a short walk from the town centre and within easy reach of Rutland Water.
This 105 square metre self-catering property features two bedrooms sleeping four, a well-equipped kitchen with integrated appliances including a dishwasher, and a modern shower room; Wednesday and Saturday markets provide access to local produce.
The Granary Barn At America Lodge, Pet Friendly In Oakham - Oakham
No reviews

The Granary Barn At America Lodge, Pet Friendly In Oakham

cottage, Oakham
This cottage is located in Oakham, Rutland, 5.1 kilometres from the nearest shop and 3.2 kilometres from the nearest pub, with Rutland Water Nature Reserve a short drive away.
This 90 square meter lodge accommodates up to four guests, featuring one bedroom with an en-suite, a kitchen with a dishwasher and air fryer, a sitting room with a sofa bed and Smart TV, and garden access with off-road parking and WiFi.
Cottage ∙ 2 Bedrooms ∙ 6 Guests - Oakham
9.0 2 reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Manton
This charming cottage is situated in the Rutland countryside, just a short walk from the village pub and the Rutland Water circular path, offering a peaceful retreat close to nature and amenities. It has received excellent ratings from previous guests, making it a popular choice for travellers seeking a comfortable and relaxing stay.
The cottage features two bedrooms, sleeping up to six guests, and offers a spacious open plan living area, perfect for families or groups. You'll find a fully equipped kitchen, a private enclosed garden, and a bike store, making it easy to explore the surrounding area and enjoy the many activities on offer, including water sports, cycling, and walking.

Frequently asked questions about holiday rentals in Oakham

  • What are some interesting places to visit in or near Oakham?

    Oakham Castle is a must-see, with its impressive gatehouse and collection of historic carriages. For something different, visit the Rutland County Museum, housed in a beautiful 17th-century building. Just outside Oakham, you can explore the picturesque Rutland Water, offering watersports, walking trails, and stunning views.
  • What are the best Airbnb and vacation rentals in Oakham?

    Rooms @ Number Six, Fennel House - Charming House In Oakham Town Centre and Cozy Nook A Cosy 2-bed House In Oakham Rutland are the most popular Airbnb and vacation rentals in Oakham among travelers.

  • Which walking or cycling routes are the best in Oakham?

    The Oakham to Burley route along the River Gwash is a lovely cycle path, while the Rutland Water Nature Reserve offers a variety of walking trails, including the 10km circular route around the reservoir. For a more challenging climb, try the route up to the top of Normanton Hill, with its panoramic views across the countryside.
  • What are the most popular Airbnbs in Oakham?

  • What sports or outdoor activites can visitors enjoy in and around Oakham?

    Rutland Water is a popular spot for watersports, with sailing, windsurfing, and kayaking available. There are also plenty of opportunities for walking, cycling, and birdwatching in the surrounding countryside. For something a bit different, try a round of golf at the Oakham Golf Club.
  • What are the best vacation rentals with a pool in Oakham?

  • What other towns or cities can be easily accessed from Oakham?

    Oakham is well-connected, with easy access to nearby towns like Stamford, Melton Mowbray, and Uppingham. You can also reach the city of Leicester by car or train in under an hour. For a day trip, consider visiting the historic city of Peterborough or the charming market town of Grantham.
  • What are the best rentals for families and kids in Oakham?

    The best rentals for families and kids in Oakham are Rutland View, The Gallery Two Bedroom Apartment and Lazy Nest Is A Lazy Comfortable Nest To Laze.

  • What amenities are commonly available in vacation rentals in Oakham?

    Vacation rentals in Oakham often offer a range of amenities, including Wi-Fi, parking, and a fully equipped kitchen. Many also have gardens, patios, or balconies, perfect for enjoying the outdoors. Some rentals even have hot tubs or swimming pools, depending on the property.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakham?

  • What time of year is best to rent a vacation rental Oakham?

    Oakham is beautiful year-round, but the best time to visit really depends on your interests. Spring and autumn are ideal for exploring the countryside, while summer offers the chance to enjoy watersports and outdoor activities. If you prefer a quieter experience, consider visiting during the winter months when the town is less crowded.

Popular destinations

Best Oakham holiday rentals with a balcony

The Gallery Two Bedroom Apartment - Oakham
9.8 113 reviews

The Gallery Two Bedroom Apartment

apartment, Oakham
The Gallery Two Bedroom Apartment is located in a peaceful area, just 24 miles from Leicester Train Station and 25 miles from the University of Leicester. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment offers a comfortable 50 square metre space, accommodating up to 4 guests in two bedrooms and one bathroom. Enjoy a fully equipped kitchen, free Wi-Fi, a private patio and balcony, and free parking on-site.
Buckingham House, Pet Friendly, With Hot Tub In Whissendine - Oakham
No reviews

Buckingham House, Pet Friendly, With Hot Tub In Whissendine

cottage, Oakham
Buckingham House, a pet-friendly holiday home in Whissendine, Rutland, is situated approximately 1 kilometre from a shop and less than 1 kilometre from a pub, offering easy access to Oakham and its attractions like Oakham Castle and Rutland County Museum.
This 105 square metre dwelling boasts two en-suite bedrooms (super-king and king-size), two sitting rooms (one with a wood-burning stove), a well-equipped kitchen with a wine chiller, a jacuzzi, a private patio with barbecue and pizza oven, and parking for three cars, comfortably accommodating up to six guests.
Dog Friendly Safari Tent, Moorhen At Exton Park, Rutland - Oakham
No reviews

Dog Friendly Safari Tent, Moorhen At Exton Park, Rutland

cabin, Exton
This luxury safari tent, part of Exton Park's walled garden in Rutland, offers a tranquil escape less than 3km from Rutland Water and 20 minutes from Peterborough.
Sleeping up to six guests in three bedrooms, this off-grid retreat boasts a fully plumbed shower room, wood-burning stove, and proximity to Oakham Castle and Rutland Open Air Theatre.
Rutland View - Oakham
9.4 140 reviews

Rutland View

house, Oakham
Rutland View is a spacious holiday home located in Oakham, just 24 miles from Leicester Train Station and 34 miles from East Midlands Airport, offering a peaceful escape in a quiet location. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
Rutland View has 4 bedrooms and 2 bathrooms, providing comfortable accommodation for up to 8 guests across 200 square metres. Guests can enjoy a fully equipped kitchen, a private garden with a terrace, and access to a tennis court, as well as free parking and Wi-Fi.

Best pet friendly Oakham holiday rentals

Among the 83 accommodations in Oakham, here are the 4 best pet friendly rentals

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Oakham
9.1 15 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Exton
This pet-friendly house in Cottesmore, Rutland, is situated 17km from Burghley House and 24km from Rockingham Castle, offering easy access to local attractions.
The 105 square metre property sleeps four, boasting two bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, and a garden with free Wi-Fi and parking.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Oakham
8.9 7 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Langham
This Langham holiday lodge, 27 Brocklehurst at Ranksborough Hall Holiday Park, is situated 3.9km from Oakham and a short walk from The Noel Arms pub, offering easy access to Rutland Water Nature Reserve.
The two-bedroom property sleeps four, features an open-plan living space with a gas fireplace, SMEG appliances, and a Smart TV, plus off-road parking for three cars, an enclosed decking area, and a garden.
2 Bedroom Accommodation In Market Overton - Oakham
10 1 review

2 Bedroom Accommodation In Market Overton

cottage, Market Overton
Teddy's Cottage, a Grade II listed building in Market Overton, Rutland, is conveniently located within a short drive (approx. 5km) of Rutland Water and 5km from Hambleton Bakery.
This two-bedroom holiday home sleeps four, boasting a well-equipped kitchen with a dishwasher, enclosed garden, free Wi-Fi, bike storage, and proximity to scenic footpaths and the Lodge Trust.
Beautiful Grade Ii Listed, Fully Renovated Cottage - Oakham
10 15 reviews

Beautiful Grade Ii Listed, Fully Renovated Cottage

apartment
Finches Cottage, a three-bedroom house, is situated on the outskirts of Egleton, Rutland, approximately a few kilometres from Rutland Water, offering easy access to watersports and outdoor activities.
This fully renovated property sleeps six, boasting a John Lewis kitchen, enclosed garden with BBQ (high season), log burner (winter months), and pet-friendly features including wicker beds and blankets; nearby dog-friendly pubs add to its appeal.
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