Oakham holiday lettings

We found 170 holiday rentals — enter your dates for availability

Discover a selection of 23 homes, 18 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.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Oakham

  • Charming outdoor adventures: Oakham is perfect for eco-conscious tourists with beautiful nature reserves and picturesque surroundings.
  • Rich cultural experiences: Explore historic houses and captivating castles that appeal to history buffs and families alike.
  • Friendly atmosphere: Enjoy a warm, welcoming vibe that makes it ideal for a relaxing getaway.
  • Diverse accommodation options: Choose from delightful cottages, cosy apartments, and spacious holiday homes to suit all preferences.
  • Budget-friendly getaway: Oakham offers various budget options, making it accessible for families and all types of travellers.

Popular types of accommodation in Oakham

Planning a getaway to Oakham? You’re in for a treat! This charming town offers a variety of accommodation options, including delightful cottages, cosy apartments, and spacious houses. Whether you’re searching for a romantic one-bedroom cottage or a family-friendly holiday retreat, Oakham has something to suit every taste. Explore the best holiday cottages and discover the perfect base for your adventure.

  • Apartments: The most sought-after accommodation in Oakham, offering modern amenities and convenient locations for an enjoyable stay.
  • Houses: A fantastic choice for those seeking space and privacy, ideal for families and groups.
  • Cottages: Charming and quaint, these traditional homes provide a cosy retreat and a taste of rural England.
  • Caravan Parks: A popular option for those looking to embrace the great outdoors, with facilities for camping and touring caravans.
  • Cabins: Perfect for a peaceful getaway, these rustic lodgings allow you to immerse yourself in nature.**

Top attractions in Oakham

Oakham offers a delightful mix of outdoor adventures and cultural experiences, making it an ideal destination for eco-conscious tourists. Visitors can explore historic houses, nature reserves, and captivating castles that cater to families and culture enthusiasts alike. Whether you're seeking adventure or a leisurely day out, Oakham has something for everyone, ensuring a memorable stay.

  • Rutland Water Nature Reserve: A stunning natural haven, this reserve features scenic walking trails, diverse wildlife, and picturesque views of the water. Ideal for nature enthusiasts and tranquil escapes.
  • Oakham Castle: This historic castle boasts impressive architecture and rich cultural heritage. It's a romantic spot perfect for leisurely exploration and appreciating medieval history.
  • Barnsdale Gardens: A beautifully landscaped botanical garden, offering a relaxing outdoor experience. Perfect for families, it features various themed gardens that inspire and delight visitors.

Things to do recommended for couples

For a romantic getaway in Oakham, consider a visit to Rothley Wine, located 11.2km away. Enjoy a delightful day sampling exquisite wines in a charming setting, perfect for couples seeking a blend of romance and entertainment.

Things to do recommended for families

Families will love exploring Rutland Water Country Park for a relaxing day outdoors, racing at Nottingham Raceway Karting for an adrenaline rush, and swimming at the International Swimming Pool for some sporty fun. These activities promise memorable experiences for everyone!

Things to do recommended for groups

Enjoy a round of golf at Stapleford Park Golf Course, just 4.3km from Oakham, or immerse yourselves in culture at the Curve Theatre, 14.3km away. For a creative afternoon, visit the Paint A Pot Place, 9.9km from Oakham, and unleash your artistic flair.

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

When travelling with a group, family, pets, or seeking extended stays, it’s essential to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for 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 space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • 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 facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Oakham: For many, a family holiday isn’t truly fulfilling without their four-legged companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Oakham: If you’re in search of holiday rentals with special offers for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. It may also be worth considering additional features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Oakham

Discover the charm of Oakham, a delightful town perfect for outdoor and eco-friendly adventures. With its friendly atmosphere and budget-friendly options, it's an ideal getaway for families. Explore the picturesque surroundings, enjoy relaxing strolls, and immerse yourself in the local vibe. Nearby attractions offer a mix of recreation and business, making Oakham a versatile destination for all types of travellers seeking an idyllic location for their next holiday.

  • Uppingham: Nestled close to Oakham, Uppingham is a charming village that beckons outdoor enthusiasts and adventure seekers alike. Surrounded by picturesque landscapes, this quaint locale offers a delightful travel experience with its scenic recreation park and ample shopping areas. Nature lovers will appreciate the nearby nature reserve and national park, providing opportunities for exploration and relaxation. The village’s serene water feature adds to its appeal, making it an ideal spot for a leisurely day out.
  • Barnsdale: Located in the vicinity of Oakham, Barnsdale is a delightful village perfect for those in search of eco-friendly adventures and outdoor activities. Visitors can enjoy the lush recreation park and unwind at the local spa, making it a great destination for relaxation and rejuvenation. The area is rich with natural beauty, featuring stunning water features and a nature reserve that enhances the experience. The proximity to a national park ensures a wealth of exploration opportunities for nature enthusiasts.
  • Empingham: Just a stone's throw from Oakham, Empingham is a picturesque village that offers a wonderful blend of outdoor adventure and eco-conscious activities. With a range of recreational areas and a golf course, it caters to sports lovers and families looking for fun. The nearby water feature and nature reserve provide a scenic backdrop for leisurely strolls, while the historic house adds a touch of heritage to your visit. Empingham is the perfect base for exploring the natural beauty of the region.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or easily view and organise your travel plans. You can now find the properties you've saved and booked neatly sorted into Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/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:

  • The Rutland Falconry and Owl Centre (2.5 mi / 4 km)
  • Rutland Water Golf Course (3.6 mi / 5.8 km)
  • Stapleford Park Golf Course (6.5 mi / 10.5 km)
  • Twinlakes Park (9.6 mi / 15.4 km)
  • International Swimming Pool (12.6 mi / 20.3 km)
  • Leicestershire Golf Club (15.6 mi / 25 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)
  • Barnsdale Gardens (3.4 mi / 5.5 km)
  • Stamford Meadows (10.4 mi / 16.7 km)
  • Victoria Park (16.7 mi / 26.9 km)
  • Abbey Park (17.2 mi / 27.6 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.
How much does it cost to rent a holiday home in Oakham?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakham holiday house rentals?
You can find great discounts on house rentals in Oakham on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Oakham?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Oakham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Oakham holiday rental?
Book your Oakham holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Oakham home rental booking on Vrbo?
To find Oakham holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oakham holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas