Oakham holiday rentals

We found 182 holiday rentals — enter your dates for availability
Discover a selection of 22 homes, 16 apartments and other holiday rentals in Oakham that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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Why visit Oakham

  • Historic Oakham Castle: Explore this impressive medieval landmark that showcases the rich history of the town.
  • Beautiful Rutland Water: Enjoy outdoor activities such as walking, cycling, and birdwatching around this stunning reservoir.
  • Charming Market Town Atmosphere: Wander through picturesque streets filled with unique shops and local eateries.
  • Engaging Community Events: Participate in various guided tours and local festivities that highlight Oakham's vibrant culture.
  • Eco-friendly Adventures: Experience a range of outdoor pursuits in a tranquil setting, perfect for nature lovers.

Popular types of accommodation in Oakham

Welcome to Oakham, a charming market town in England's picturesque Rutland. Known for its historic architecture and stunning natural surroundings, Oakham offers a delightful array of accommodation options. From cosy cottages to private holiday homes and modern apartments, you’ll find the ideal retreat here. Explore local attractions like Oakham Castle and the beautiful Rutland Water, or relax in friendly hotels that epitomise comfort and hospitality. Discover the perfect base for your next holiday adventure in Oakham.

  • Apartments: The most sought-after choice, offering modern comforts and stylish living spaces for a delightful stay in Oakham.
  • Private Holiday Homes: Renowned for their exclusivity, these self-catering homes provide a cosy retreat for families and couples alike.
  • Cottages: Charming and quaint, these traditional dwellings invite you to experience a quintessential British holiday.
  • Caravan Parks: Perfect for the adventurous traveller, these sites offer a unique blend of nature and comfort.
  • Cabins: Ideal for a rustic escape, these snug abodes provide a serene setting amidst the countryside.**

Top attractions in and around Oakham

Oakham, England, offers a charming mix of history and outdoor adventure, making it ideal for eco-friendly holidays. Explore the impressive Oakham Castle, a historic landmark, and enjoy the natural beauty of local reserves and preserves. With its rich cultural heritage and family-friendly attractions, Oakham invites travellers to engage in guided tours and experience the vibrant community, ensuring a memorable visit for all.

  • Rutland Water Nature Reserve: A stunning natural haven, this reserve offers picturesque walking trails, birdwatching opportunities, and serene views of the expansive water, perfect for picnics and outdoor activities.
  • Burghley House: An impressive Elizabethan stately home, renowned for its grand architecture and beautiful gardens, where visitors can explore art collections and historical exhibitions.
  • Belvoir Castle: A magnificent castle with a romantic atmosphere, featuring beautifully landscaped grounds and rich history, ideal for a leisurely day exploring its opulent interiors.

Things to do recommended for couples

Discover the charm of Oakham with a stroll along its historic streets, hand in hand, or enjoy a romantic picnic at Oakham Castle. Don’t miss a candlelit dinner at a local restaurant, where you can savour exquisite British cuisine together.

Things to do recommended for families

Families will delight in exploring Oakham Castle, with its fascinating history and impressive architecture. The Rutland Water Nature Reserve offers a chance for outdoor adventures, including cycling and birdwatching, ensuring a memorable experience for all ages.

Things to do recommended for groups

Groups visiting Oakham can discover the historic Oakham Castle, enjoy a leisurely stroll around Rutland Water, and experience local flavours at the bustling Oakham Market, perfect for sampling regional delicacies and artisan products.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Oakham

Whether you’re travelling with a group, as a family, with your pets, or planning an extended stay, ensure you filter using the appropriate priorities. Below are some Stayz booking tips to help you.

  • Traveling to Oakham with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these features and much more on Stayz.
  • Traveling to Oakham with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Oakham: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakham: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Oakham

Oakham offers a delightful blend of outdoor adventures and eco-friendly holidays. Explore its charming streets, enjoy the relaxing atmosphere, and discover local experiences such as the renowned oakham school and cosy cottage holidays in the city. With a friendly, budget-conscious vibe and easy reach to nearby attractions, Oakham provides a perfect retreat for those seeking both adventure and tranquillity in the heart of England.

  • Uppingham: Nestled in the charming countryside near Oakham, Uppingham is a picturesque village renowned for its vibrant culture and outdoor adventures. Visitors are drawn to its scenic recreational areas and lively music concerts. Stroll through the village to discover local landmarks, including a beautiful water feature and a serene nature reserve. Uppingham's historic places add a touch of heritage to your exploration, making it an ideal spot for those seeking both relaxation and cultural enrichment.
  • Greetham: Situated close to Oakham, Greetham is a delightful village that offers an eco-friendly escape for outdoor enthusiasts. The area is perfect for those who enjoy golf and various sports amidst stunning natural landscapes. Explore the local recreational areas and nearby national parks, where you can immerse yourself in the tranquillity of nature reserves and picturesque water features. Greetham's emphasis on sustainability and outdoor adventure makes it a fantastic choice for eco-minded travellers.
  • Cottesmore: Cottesmore, a quaint village just a stone's throw from Oakham, is ideal for visitors seeking breathtaking scenery and outdoor activities. The village boasts numerous recreational areas and educational attractions, perfect for families and nature lovers. Explore the nearby national state park and nature reserves, where you can enjoy stunning landscapes and diverse wildlife. Cottesmore's serene setting and emphasis on outdoor exploration make it a wonderful destination for those looking to unwind and connect with nature.

Best time to go to Oakham

If you're planning a trip to Oakham, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in April, July and September, while off-peak times, like February, October and December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January38.7°F (3.7°C)Light RainMostly CloudyAverageSlightly Low
February39.9°F (4.4°C)No Rain (Dry)Mostly CloudySlightly LowSlightly Low
March42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
April46.6°F (8.1°C)No Rain (Dry)Mostly CloudySlightly HighAverage
May52.2°F (11.2°C)Light RainMostly CloudyAverageAverage
June57.7°F (14.3°C)Light RainMostly CloudyAverageAverage
July61.9°F (16.6°C)Light RainMostly CloudySlightly HighSlightly High
August62.1°F (16.7°C)Light RainMostly CloudyAverageSlightly High
September58.1°F (14.5°C)Light RainMostly SunnySlightly HighAverage
October52.2°F (11.2°C)Light RainMostly CloudySlightly LowAverage
November45.1°F (7.3°C)Light RainMostly CloudyAverageAverage
December40.8°F (4.9°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Stayz is a breeze

Are you eager to make your next journey more economical? Consider being flexible with your travel dates, as prices often fluctuate. Additionally, you could secure substantial savings by opting for an extended stay. To locate a Stayz property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board offers a user-friendly platform to plan your journeys, resume previous activities, or organise your travel arrangements. You’ll find your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The friendly area of Oakham awaits your stay

The gardens, lake and countryside are the perfect backdrop to your holiday home in Oakham. This welcoming and relaxing city entices travellers with its bars and restaurants. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Oakham

Are you looking for attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Oakham a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Twinlakes Park (9.6 mi / 15.4 km)
  • Belton Woods Hotel, Spa & Golf Resort (19.4 mi / 31.2 km)
  • Thorpe Wood Golf Course (19.7 mi / 31.6 km)
  • Wicksteed Park (19.8 mi / 31.9 km)
  • Cosby Golf Club (21.5 mi / 34.5 km)
  • Activity World (22.5 mi / 36.2 km)

Exploring the natural features in Oakham

Travellers enjoy Oakham for its gardens, lakeside setting and countryside. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oakham is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Rutland Water Country Park (1.9 mi / 3.1 km)
  • Rutland Water Nature Reserve (2 mi / 3.2 km)
  • Victoria Park (16.7 mi / 26.9 km)
  • Abbey Park (17.2 mi / 27.6 km)
  • Ferry Meadows Country Park (18.8 mi / 30.3 km)
  • Wicksteed Park (19.8 mi / 31.9 km)

How to get to and around Oakham

The nearest airport is in Nottingham (NQT), located 22.7 mi (36.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into East Midlands Airport (EMA), which is 27.4 mi (44.1 km) away.

If you prefer train travel, you can make your way to Oakham Station.

Frequently asked questions

What is the best area to stay in Oakham when booking a holiday rental?
When considering the best area to stay in Oakham for a holiday rental, the town centre is a fantastic choice. This vibrant area boasts a charming atmosphere, with a selection of delightful shops, cafés, and restaurants that invite you to explore the local cuisine and culture. The historic Oakham Castle is a must-visit attraction, showcasing impressive architecture and fascinating exhibitions that reflect the town's rich heritage.Another excellent option is the neighbourhood surrounding Rutland Water, which is renowned for its stunning natural beauty and outdoor activities. Here, you can enjoy picturesque walks, cycling paths, and birdwatching opportunities, making it great for nature lovers. The area is also home to various holiday rentals, providing a range of options to suit different preferences.
What is the most popular type of holiday rental accomodation in Oakham?
In Oakham, cottages are the predominant type of holiday rental, with around 316 available throughout the area. These charming properties are often situated in picturesque neighbourhoods, providing a quintessential English countryside experience. Most cottages are equipped with fully fitted kitchens, inviting living rooms, and often feature gardens or outdoor seating areas, great for enjoying the serene surroundings.Additionally, there are approximately 76 cabins and 76 holiday houses, which offer similar amenities but can vary in size and layout, suiting different group sizes. For those seeking a more urban feel, around 56 apartments are available, typically located close to local shops and eateries, providing a comfortable base for exploring Oakham.
Are there any family house rentals in Oakham?
In Oakham, there are numerous family-friendly house rentals available, with around 63 options to choose from. The town is steeped in history and offers a charming atmosphere, making it an ideal location for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and gardens or outdoor spaces where children can play safely.Visitors can enjoy amenities such as Wi-Fi and parking, ensuring a comfortable stay. Oakham is also well-positioned for exploring local attractions, including the picturesque Rutland Water, which is great for outdoor activities like cycling and birdwatching. The nearby Oakham Castle provides a glimpse into the town's rich heritage, making it an exciting outing for families.
Can I rent a holiday home with a pool or hot tub in Oakham?
In Oakham, there are several holiday homes available for rent that feature pools and hot tubs, with around 27 options to choose from. This charming town in the heart of Rutland offers a delightful mix of countryside views and local attractions. Many of these properties come equipped with private swimming pools, relaxing hot tubs, and spacious outdoor areas superb for enjoying the scenic surroundings.Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often, barbecue facilities for those warm summer evenings. Some rentals may also include access to gardens or patios where families can unwind. Find your rental in Oakham with a pool or a hot tub.
Are there pet-friendly house rentals in Oakham?
In Oakham, there are a number of pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with convenient amenities such as fully fitted kitchens, spacious living areas, and private gardens, allowing for a comfortable stay while suiting the needs of your furry companions.The town is surrounded by picturesque countryside, making it ideal for long walks and outdoor adventures with pets. Nearby attractions include Rutland Water, which offers beautiful trails and scenic views, superb for a day out with your pet. Additionally, the charming local parks and green spaces provide ample opportunities for relaxation and play. See all pet-friendly rentals in Oakham.
Are there any remote work holiday rentals in Oakham?
In Oakham, there are numerous options for remote work holiday rentals, with around 444 available throughout the area. This charming market town in the heart of Rutland offers a picturesque setting for those looking to combine work and leisure. Many of these properties are equipped with essential amenities for remote work, including free Wi-Fi, ensuring a reliable internet connection for staying productive during your stay.Visitors can expect a variety of accommodations, from cosy flats in the town centre to larger properties on the outskirts, often featuring comfortable workspaces and ample natural light. The town itself is rich in history and culture, with attractions such as Oakham Castle and nearby Rutland Water, superb for unwinding after a day of work. The surrounding countryside also offers beautiful landscapes, ideal for outdoor activities and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oakham?
In Oakham, popular rental amenities include kitchens, which allow guests to prepare their own meals and enjoy home-cooked dining experiences. Many properties also permit pets, making it a suitable destination for animal lovers travelling with their furry companions. Onsite parking is commonly available, providing convenience for those arriving by car. Additionally, many rentals are equipped to accommodate service animals, ensuring accessibility for all guests. Outdoor spaces such as gardens are also a feature, offering a tranquil setting for relaxation and enjoying the fresh air.
When is the best time to visit Oakham for a holiday rental?
September is the most popular time to visit Oakham for a holiday rental, as it falls just after the peak season from July to August. During this month, the weather is often still quite pleasant, with average temperatures ranging from 10 to 20 degrees Celsius, making it ideal for outdoor activities and sightseeing.As summer transitions into autumn, visitors can enjoy quieter streets and fewer crowds, allowing for a more relaxed experience while exploring the charming market town. Oakham is known for its picturesque scenery, historic sites, and delightful local shops, all of which can be comfortably explored during this time.If you're looking for a more budget-friendly option, consider visiting in December. While this is the low season, it offers a unique charm with festive decorations and the opportunity to enjoy seasonal events without the hustle and bustle. The crisp winter air can be invigorating, great for cosy strolls around the town or visiting local pubs.Ultimately, the best time to visit Oakham depends on whether you prefer the lively option of late summer or the quaint, festive spirit of early winter.
What are the top attractions in Oakham?
In Oakham, visitors can explore a variety of attractions that showcase the town's rich history and picturesque scenery. The historic Oakham Castle, a remarkable 12th-century Norman castle, is a must-see, featuring impressive architecture and a collection of unique wooden horseshoes. The Rutland County Museum offers insights into the local heritage, with exhibits ranging from archaeology to social history, making it an engaging stop for those interested in the area's past.The beautiful Rutland Water, located just a short distance from the town, is superb for outdoor enthusiasts, offering opportunities for walking, cycling, and birdwatching, as well as water sports such as sailing and kayaking. Additionally, the charming streets of the town centre are lined with independent shops, cafes, and local markets, providing a delightful shopping experience.For those seeking a taste of local culture, the Oakham Theatre hosts various performances throughout the year, showcasing both local talent and touring productions.
Are all fees included in the Oakham holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oakham holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oakham holiday homes?
You can find great discounts on holiday homes in Oakham on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oakham holiday home booking on Stayz?
To find Oakham holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakham?
A long-stay holiday home in Oakham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakham holiday home?
Book your Oakham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakham?
Prices for holiday homes in Oakham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakham to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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