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A historic building with a tower by a lake, a picnic table, and a grassy area.

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    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Oakham holiday rentals

    1. Bennett's Cottage

    A quaint cottage with a white door, a small window, and a sign reading "Bennett's Cottage".

    2. 2 bedroom accommodation in Oakham

    A cozy living room with a sofa, teal cushions, a wooden dining table with chairs, a kitchen in the background, and a brick wall with a clock.

    3. 2 bedroom accommodation in Market Overton

    A red door with a white window, a brick building with ivy, and a clear sky.

    4. Stylish 2-Bed Apartment | Oakham High Street

    A modern kitchen with light-colored cabinets, a wooden dining table set with plates and a wine glass, and a clock on the wall.

    5. Gardeners Cottage

    A modern kitchen with a central island, a dining area with a bench, and a skylight above.

    6. Flat 2, The Maltings

    A stone building with a sign reading "THE MALTINGS".

    7. The Hideout

    A traditional stone building with a sign reading "THE MALTINGS".

    8. 9 Rectory Lane

    A stone house with a gravel driveway, a small garden, and a wooden deck.

    9. Buckingham House

    A hot tub in front of a brick building with an open door leading to a living room.

    10. Manor View

    A stone building with a white door, a small window, and a wall-mounted light fixture.

    11. Amberleigh

    A living room with a leather sofa, a television, a fireplace, and a red wall.

    12. Bee Hive

    A wooden structure with a circular opening, a bench, and a view of a river and greenery.

    13. Squirrel's Nest

    A wooden structure with a circular opening, a bench, and a view of a river and greenery.

    14. Rabbit Hole

    A wooden structure with a circular opening, a bench, and a view of a river and greenery.

    15. Bumble Bee

    A stone house with a green door, a stone pathway, and a neatly trimmed hedge.

    16. Otter's View

    A wooden structure with a circular opening, a bench, and a view of a river and greenery.

    17. Badger's Burrow

    A wooden structure with a view of a river and trees.

    18. Farm View House

    A modern kitchen with a large island, white cabinetry, and a hanging light fixture.

    19. Luxury Shepherd Hut situated on a private 30 acre estate in the heart of Rutland

    A modern kitchen with a built-in stove, wooden cabinets, and a window.

    20. The Gresham Aparthotel

    A historic building with a corner turret, large windows, and a sign indicating a bicycle parking zone.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Top Oakham Hotel Reviews

    Rectory Farm Annexe

    A stone house with a steeply pitched roof, a chimney, and a blue door.

    Hambleton Hall

    A large, historic building with a formal garden, including a fountain and manicured hedges.

    Church Farm Lodge

    A living room with a TV, a table with a vase of flowers, and a large window with a view of a grassy area.

    The Manor House at Quorn

    A dining area with multiple tables, chairs, and a fireplace.

    The White Lion Inn

    A wooden table with wine glasses, a bottle of Grand Venuur, and a vase with dried flowers.

    The Old Stables

    A modern bedroom with a bed, two armchairs, a small round table, and a large mirror.

    Crown Hotel Stamford

    A cobblestone street lined with historic stone buildings, featuring arched windows and a traditional architectural style.

    The Crown Inn

    An open door leading to a room with a fireplace, a dining table with a bottle and glasses, and a white chair outside.

    The Talbot Hotel, Oundle, Northamptonshire

    A historic building with a central courtyard, stone walls, and traditional architecture.

    The Bell Inn Hotel, Stilton, Cambridgeshire

    A cozy room with a fireplace, a table set for tea, and comfortable seating.

    The Old Pheasant Hotel

    A courtyard with stone buildings, outdoor seating, and a variety of plants.

    The Belmont Hotel

    A building with a white facade, a staircase with black railings, and a sign reading "BELMONT DE MONTFORT STREET".

    The White Hart

    A traditional stone building with a thatched roof, surrounded by a wooden fence and a garden with daffodils.

    The Stanwick Hotel

    An indoor restaurant with hanging plants, blue chairs, and a brick wall.

    Kilworth House hotel & Theatre

    A grand hotel lobby with a high ceiling, ornate chandeliers, and a reflective floor.

    The Poplars Moulton

    A neatly made bed with a striped bedspread, a decorative pillow, and a framed artwork above it.

    Old White Hart

    A dining area with wooden beams, large windows, and a table set for two.

    The Wisteria Hotel

    A bar area with a wooden counter, a red suitcase, and a chalkboard menu.

    The Barnsdale, Rutland

    A spacious indoor dining area with high ceilings, large windows, and a rustic stone wall. Tables are set with candles and chairs are arranged for dining.

    Rushton Hall Hotel & SPA

    Exterior

    Find out more about Oakham

    Everything you need to know about Oakham holiday rentals

    Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Oakham holiday rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Oakham. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Oakham holiday rentals we have selected for you start as low as £72 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Oakham rentals

    At Expedia, we put the best Oakham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Oakham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakham holiday.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find a holiday rental in Oakham?

    Yes, there are holiday rentals in Oakham close to Barnsdale Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Oakham has a good selection of top-notch restaurants and lively bars. Make sure you allow time to enjoy the gardens and lakeside.

    What are some of the best holiday rentals that Oakham has to offer?

    3 Bed House - Sleeps 6 - Parking - Wifi: This holiday home rental outside of Oakham comes with free WiFi so that you can feel at home during your trip. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

    How many holiday rentals will I find in Oakham?

    With 22 Expedia holiday rentals, you're guaranteed to find just the right place for your Oakham stay.

    What’s there to see and do in Oakham?

    Rutland Water Country Park and Rutland Water Nature Reserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include The Rutland Falconry and Owl Centre. Barnsdale Gardens and Lyddington Bede House are other places to visit while you're in town.

    What’s a holiday rental in Oakham like?

    Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakham. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.

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