Photo by Jules & Jenny

Uppingham holiday homes

We found 164 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Uppingham to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Uppingham

  • Rich Heritage: Stroll among Uppingham’s historic buildings and houses that whisper tales of the past.
  • Natural Reserves: Enjoy the preserved reserves perfect for leisurely outdoor walks and family picnics.
  • Charming Central Area: Wander through the heart of town, soaking up the inviting village vibes.
  • Cultural Insights: Experience artistic and historical landmarks that enrich your visit.
  • Family-Friendly Atmosphere: Revel in the relaxed, budget-friendly environment ideal for a memorable holiday.

Top attractions near Uppingham

Discover the charm of Uppingham, a quaint city in Oakham, England, perfect for your next outdoor and cultural adventure. Explore its historic houses, preserved reserves, and enchanting historic buildings that offer a taste of rich history and family-friendly experiences. Enjoy leisurely walks, artistic insights, and a relaxed atmosphere that makes your visit truly memorable.

  • Rutland Water Nature Reserve: A stunning natural haven ideal for birdwatching, cycling, and walking. The expansive reservoir offers picturesque views and diverse wildlife, making it a perfect spot for nature lovers.
  • Burghley House: An exquisite example of Elizabethan architecture, Burghley House boasts beautifully manicured gardens and rich history. Explore its impressive art collection and learn about its fascinating past.
  • Fotheringhay Castle: A historic site steeped in royalty, Fotheringhay Castle provides a glimpse into England’s past. Enjoy the scenic surroundings and imagine the events that shaped history within its walls.

Things to do recommended for couples

Experience romance in Uppingham with a leisurely stroll along the picturesque High Street, lined with charming boutiques and cafés. Enjoy a candlelit dinner at a cosy restaurant, followed by a serene walk in the nearby Rutland Water, where you can watch the sunset together. Perfect for couples.

Things to do recommended for families

In Uppingham, families can explore the charming local markets, visit the historic Uppingham School, and enjoy outdoor fun at the nearby Rutland Water, perfect for cycling and picnicking. Don't miss the delightful craft shops and cosy cafés for a true taste of English village life.

Things to do recommended for groups

In Uppingham, groups can enjoy a charming walking tour of the historic market town, visit the local art galleries, and savour traditional British fare at cosy pubs. Don't miss the opportunity to explore nearby Oakham's quaint shops and the beautiful Rutland Water for a lovely outdoor experience.

*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 Uppingham

If you're travelling with a group, your family, bringing along pets, or planning an extended stay, it's important to refine your search according to your specific needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Uppingham with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Uppingham with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Uppingham: For many families, a getaway wouldn’t feel complete without their furry companion. If this resonates with you, take a look at the Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and bedding, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Uppingham: If you're in search of holiday rentals with special offers 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 rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Uppingham

Discover Uppingham, a charming village perfect for outdoor adventures and cultural experiences. Wander through the central area and explore local landmarks within the town, taking in the warm and friendly atmosphere. Enjoy family-friendly and budget experiences, and relax in the inviting village and town vibes. Uppingham offers a unique blend of heritage and modern comforts for an unforgettable New Zealand travel adventure.

  • Oakham: Nestled in the heart of Rutland, Oakham is a vibrant city that serves as a gateway to outdoor adventures and eco-friendly experiences. With Uppingham located within its bounds, Oakham is known for its recreational parks and scenic areas that invite exploration. Visitors can enjoy activities such as golfing and leisurely walks amidst nature reserves and picturesque water features. The nearby national park offers stunning landscapes perfect for hiking and wildlife spotting, making Oakham an ideal base for those keen on outdoor pursuits.
  • Lyddington: Just 3km from Uppingham, Lyddington is a charming village that exudes a rustic charm. This idyllic spot is perfect for travellers seeking outdoor activities and an eco-conscious experience. The village features a lovely recreation park where you can unwind and soak in the tranquil atmosphere. Nearby attractions include a serene water feature and a nature reserve, providing opportunities for birdwatching and peaceful strolls. Lyddington also boasts a historic house, adding a touch of heritage to your visit.
  • Manton: Located 5km away from Uppingham, Manton is another picturesque village that beckons adventure seekers and nature lovers. The village is surrounded by stunning landscapes, including a recreation park that offers ample space for activities and relaxation. Manton’s proximity to a national park and nature reserve means you can easily immerse yourself in the great outdoors, enjoying walking trails and beautiful views. The local water feature adds to the charm, providing a perfect spot for a picnic or a quiet moment in nature.

Best time to go to Uppingham

If you're planning a trip to Uppingham, it's a good idea to check both the weather and property rates. The warmest months are July and August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January38.5°F (3.6°C)Light RainMostly CloudyAverage
February39.7°F (4.3°C)No Rain (Dry)Mostly CloudyAverage
March42.6°F (5.9°C)No Rain (Dry)Mostly CloudySlightly High
April46.6°F (8.1°C)No Rain (Dry)Mostly CloudySlightly High
May52.2°F (11.2°C)Light RainMostly CloudyAverage
June57.9°F (14.4°C)Light RainMostly CloudyAverage
July61.9°F (16.6°C)Light RainMostly CloudyAverage
August61.9°F (16.6°C)Light RainMostly CloudyAverage
September57.9°F (14.4°C)No Rain (Dry)Mostly SunnySlightly High
October52.0°F (11.1°C)Light RainMostly CloudySlightly Low
November45.0°F (7.2°C)Light RainMostly CloudySlightly Low
December40.8°F (4.9°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is simple

Are you keen to make the most of your budget on your next adventure? Being flexible with your travel dates can really pay off, as prices often fluctuate. Additionally, if you're considering a longer stay, you could unlock some considerable savings. To discover a Vrbo property that suits your financial plan, simply use our handy filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient area for you to create new adventures, continue planning your getaways, or review and manage your bookings. The properties you've saved or reserved are conveniently sorted into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Friendly Uppingham will entice you

The area's culture and history are just some of the reasons to come on holiday to Uppingham. This welcoming city attracts visitors thanks to its bars and restaurants. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Uppingham

Are you hoping to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Uppingham a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Wicksteed Park (14.2 mi / 22.8 km)
  • Twinlakes Park (14.7 mi / 23.7 km)
  • Rutland Water Golf Course (4.4 mi / 7.1 km)
  • Corby Tennis Centre (5.6 mi / 9 km)
  • The Rutland Falconry and Owl Centre (7.3 mi / 11.8 km)
  • Kettering Golf Club (14.2 mi / 22.9 km)

Exploring the natural features in Uppingham

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Uppingham is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Rutland Water Nature Reserve (4.5 mi / 7.2 km)
  • Rutland Water Country Park (4.6 mi / 7.4 km)
  • Rutland Water (5.3 mi / 8.5 km)
  • Barnsdale Gardens (7.4 mi / 11.9 km)
  • Wicksteed Park (14.2 mi / 22.8 km)
  • Victoria Park (17 mi / 27.4 km)

Travelling to and around Uppingham

The nearest airport is in Nottingham (NQT), located 27.4 mi (44.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into East Midlands Airport (EMA), which is 30.4 mi (49 km) away.

Frequently asked questions

What is the best area to stay in Uppingham when booking a holiday rental?
When considering a holiday rental in Uppingham, a charming market town in Rutland, the area around the town centre is a prime choice. This picturesque part of Uppingham boasts a delightful selection of properties, many of which are set in historic buildings that exude character and charm. Staying here places you within easy walking distance of numerous attractions, including the stunning Uppingham School, renowned for its impressive architecture and tranquil grounds.Moreover, the town's vibrant market square is a hub of activity, featuring a variety of independent shops, cafés, and restaurants, making it ideal for those who appreciate local culture and cuisine. The nearby Rutland Water, a vast reservoir, offers opportunities for outdoor activities such as cycling, walking, and birdwatching, adding a wonderful natural aspect to your stay.
When is the best time to visit Uppingham for a holiday rental?
September is the most popular time to visit Uppingham, as the summer crowds begin to dissipate and the town showcases its charming architecture and lush surroundings. This transition period allows visitors to enjoy milder weather while still engaging in outdoor activities and sightseeing without the hustle and bustle of peak tourist season.The peak season for Uppingham runs from February to April, making it an excellent choice for those seeking vibrant local events and a lively option. During these months, you can explore the town's quaint streets and enjoy the various spring festivals, all while temperatures are generally pleasant, ranging from 5 to 15 degrees Celsius.If you're considering a visit, December offers a wonderfully quiet experience with the added charm of festive decorations. Although it is considered low season, this time provides a unique opportunity to appreciate the town's tranquillity, great for leisurely strolls and cosy evenings in local pubs.For those who prefer a balance of good value and pleasant weather, September stands out as an ideal time to book your holiday rental in Uppingham. You can revel in the beauty of the English countryside while enjoying the comfort of fewer tourists, allowing for an intimate experience of this delightful town.
What are the top attractions in Uppingham?
In Uppingham, visitors can enjoy a charming market town atmosphere, rich in history and culture. The Uppingham School, a prestigious independent school, features impressive architecture and beautiful grounds that can be appreciated by those exploring the area. The town's picturesque market square is surrounded by quaint shops, cafes, and pubs, making it a lovely spot to relax and soak in the local vibe.Nearby, the Rutland Water Nature Reserve offers a range of outdoor activities, including walking, cycling, and birdwatching, providing a scenic escape just a short distance from the town centre. Additionally, the historic St. Peter and St. Paul's Church, known for its stunning stained glass windows and distinctive tower, is a must-visit for those interested in local heritage.
Are all fees included in the Uppingham holiday homes prices shown on Bookabach?
Bookabach 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 Uppingham holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Uppingham 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 Uppingham holiday homes?
You can find great discounts on holiday homes in Uppingham on Bookabach, 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 Uppingham holiday home booking on Bookabach?
To find Uppingham holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Uppingham?
A long-stay holiday home in Uppingham 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 Bookabach?
Bookabach'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 Uppingham holiday home?
Book your Uppingham 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Uppingham?
Prices for holiday homes in Uppingham 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. Bookabach offers something for every taste and budget, from affordable homes in Uppingham to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas