Compare Vacation Rentals & Airbnb in Oakham

83 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Oakham vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

83 Rentals and Airbnb in Oakham

Best family friendly Oakham vacation rentals

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

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Oakham
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Langham
This family-friendly cottage in Langham is located within easy reach of Rutland Water, just a few kilometers away, and the county town of Oakham, approximately 3 kilometers distant.
Offering accommodation for up to four guests across two bedrooms, this property includes Wi-Fi, a dishwasher, parking, and electric car charging, with convenient bike storage and proximity to outdoor pursuits.
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.
High Street Apartment - Oakham
9.8 158 reviews

High Street Apartment

apartment, Uppingham
This charming apartment is located in Uppingham, a picturesque market town in the English countryside, just 50 kilometres from Nottingham, 27 kilometres from Leicester, and 40 kilometres from Northampton. It has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering property is spread over 8 square metres and comfortably accommodates up to 5 guests in its 3 bedrooms and 1 bathroom. It features a fully equipped kitchen, a private garden, a tennis court, and free Wi-Fi, making it perfect for families or groups of friends looking for a relaxing and enjoyable stay.
Hunky Dory Cottage, Central Oakham, Rutland - Oakham
10 63 reviews

Hunky Dory Cottage, Central Oakham, Rutland

apartment
This charming cottage is located in the centre of Oakham, just a short walk from Mill Street, Oakham Castle, and the town's amenities. The cottage boasts excellent ratings for cleanliness, location and user experience, ensuring a comfortable stay.
The cottage has three bedrooms, sleeping up to six guests, and a spacious dining room, lounge and a new kitchen. The cottage offers a private courtyard, a bathroom with a shower/bath, and a downstairs toilet, as well as a fully equipped kitchen and free Wi-Fi.

Best Oakham vacation rentals with parking

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.
Luxury Rural Retreat Near Rutland Water - Oakham
9.6 182 reviews

Luxury Rural Retreat Near Rutland Water

farm
This farm stay is situated in Greetham, Rutland, within easy reach of Exton Park, Rutland Water, and the market towns of Oakham and Stamford. The accommodation is highly rated, with excellent reviews for its cleanliness, location, and overall experience.
The apartment is located above the stables, offering a unique and charming experience. It can accommodate up to 5 guests and features a private patio, a modern kitchen with a fridge and microwave, and access to the farm's working yard. Guests can enjoy the nearby pubs, explore the local attractions, and immerse themselves in the rural charm of the area.
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.
Kite - Exton Park - Oakham
8.5 2 reviews

Kite - Exton Park

house, Exton
The Kite - Exton Park is a luxury tent located in Exton Park, Exton, 3.4 kilometres from the Rutland Railway Museum and 17.7 kilometres from Burghley House.
This three-bedroom accommodation sleeps up to eleven guests and features a fully equipped kitchen, a fireplace, a barbecue area, and private parking, with opportunities for golfing, fishing, and cycling nearby.

Frequently Asked Questions about vacation 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 history dating back to the 12th century. For a dose of nature, Rutland Water is a short drive away, offering watersports and scenic walks. If you're interested in history, the nearby town of Stamford is a charming place with a wealth of historic buildings.
  • 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 Rutland Water Nature Reserve has a variety of walking trails, with the 10km circular route around the reservoir being particularly popular. For cyclists, the scenic route along the A606 towards Stamford is a good option, offering rolling hills and picturesque villages.
  • What are the most popular Airbnbs in Oakham?

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

    Rutland Water is a haven for watersports, with sailing, windsurfing, and kayaking all popular activities. There's also a golf course and a number of fishing spots. For those who prefer land-based activities, there are plenty of walking and cycling trails in the area.
  • What are the best vacation rentals with a pool in Oakham?

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

    Stamford is a charming market town just a short drive away, known for its historic architecture and independent shops. The city of Leicester is also easily accessible, offering a wider range of attractions, including museums, theatres, and shopping.
  • What are the best rentals for families and kids in Oakham?

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

    Vacation rentals in Oakham typically offer basic amenities like Wi-Fi, a washing machine, and a kitchen. Some may also have a garden or patio, and some even offer a hot tub or swimming pool.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakham?

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

    The best time to visit Oakham is during the spring or autumn, when the weather is mild and the crowds are smaller. Summer can be busy and hot, while winter can be cold and wet.
  • What are the local dishes in Oakham region?

    The region is known for its hearty pub food, with dishes like steak and ale pie and fish and chips being popular choices. There are also a number of restaurants serving international cuisine, but you'll find that many of the local pubs offer a good selection of traditional English dishes.

Popular destinations

Best Oakham vacation rentals with a balcony

Osprey Cottage, Manton In Rutland - Oakham
9.9 291 reviews

Osprey Cottage, Manton In Rutland

house, Manton
Osprey Cottage is located in Manton, Rutland, just 35 kilometres from De Montfort University and 42 kilometres from Kelmarsh Hall, making it ideal for exploring the surrounding countryside. The cottage has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The cottage has two bedrooms and one bathroom, covering a floor area of 51 square metres. It features a well-equipped kitchen with a dishwasher, oven, and microwave, a peaceful garden with a patio, and a baby safety gate, making it suitable for families and pet owners.
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.
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.
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.

Best pet friendly Oakham vacation 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.
Osprey - Exton Park - Oakham
9.0 1 review

Osprey - Exton Park

house, Exton
Osprey - Exton Park, a three-bedroom house in Exton, Leicestershire, is situated 19km from Burghley House and 26km from Rockingham Castle.
This self-catering property sleeps up to 11 guests, boasts a private garden, free on-site parking, and a fireplace, with towels and bed linen provided; cycling opportunities are available nearby.
Cosy Contryside Annex - Oakham
10 17 reviews

Cosy Contryside Annex

apartment
This Pilton annex apartment is situated near Rutland Water, offering easy access to scenic countryside walks and cycle routes.
The self-contained flat sleeps two adults and two children, boasting a king-size bed, double sofa bed, small kitchen, and private parking, plus a travel cot and highchair are available on request.
Shepherd's Hut With Wood-fired Hot Tub And Epic Views Over Rutland Water - Oakham
No reviews

Shepherd's Hut With Wood-fired Hot Tub And Epic Views Over Rutland Water

cabin, Rutland
This shepherd's hut, located in Oakham, Rutland, offers waterfront access to Rutland Water, close proximity to Oakham Castle and Rutland Water Nature Reserve.
The 15-square-metre self-contained unit sleeps one, featuring a private wood-fired hot tub with Rutland Water views, an en-suite bathroom, outdoor cooking facilities, and includes Wanderlust Camping Club membership.
©2026 cozycozy.com