Holiday rentals in Oakham

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Quick stats about holiday rentals in Oakham

  • Total holiday rentals

    Explore 50 holiday rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at €53 per night before taxes and fees

  • Verified guest reviews

    Over 2,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Oakham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakham rentals

  • 4.9 Average rating

    Oakham stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Oakham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage
5 out of 5 average rating, 61 reviews

Hunky Dory Cottage, Central Oakham, Rutland

Our recently renovated 'home from home' is situated in the heart of Oakham with the boutique shops of Mill Street and many cafés, bars and restaurants of Oakham on its doorstep. The castle & park are an easy walk away as are all the towns amenities & attractions. The cottage is surrounded by roses and has been decorated by the owner, Jane, in her own unique style. All 3 beds are king size making it ideal for small families or up to 3 couples with good size dining room, lounge and a new kitchen.

Top guest favourite
Apartment
4.99 out of 5 average rating, 86 reviews

Healey House The Annex

Set in the small village of Braunston, The Annex overlooks the rolling hills and beautiful Rutland countryside. Ideal for couples, this one bedroomed apartment has a full kitchen, cooking facilities, an open plan living area and downstairs toilet. On the first floor, a large double bedroom with a king-size bed, an en-suite shower, and toilet, along with a set of french doors leading out to a small balcony. The apartment is self-contained with its own access and large south facing patio doors.

Top guest favourite
A freestanding brass bathtub occupies the foreground, reflecting warm light. Behind it, a luxurious four-poster bed is framed by elegant wooden beams and soft textiles. Personalised robes hang on hooks nearby, enhancing the room’s serene character. Artwork of animals adorns the walls, adding charm.
Barn
5 out of 5 average rating, 539 reviews

Hunters Lodge Warwickshire

A luxurious self catered barn conversion offering a unique and romantic escape nestled in the picturesque Warwickshire countryside. A place to relax and unwind whether it’s in our gorgeous freestanding bath tub, our 4 poster bed or by putting your feet up in front of the log burner and enjoying the warm and ambient glow. Take a dip in our traditional outdoor spa bath tub situated in your private patio area and watch the sunset across the fields. This is truly a stunning and unforgettable stay.

Top guest favourite
Townhouse
4.99 out of 5 average rating, 179 reviews

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. The fenced garden has a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included

Top guest favourite
A charming stone exterior of the cottage is visible, featuring several windows complementing the rustic facade. Flower pots with greenery are arranged along a gravel pathway, while a small bench provides a resting spot. Sunlight brightens the area, enhancing the inviting ambiance.
Cottage
4.93 out of 5 average rating, 104 reviews

Lovely Cottage In Pretty Village Nr Rutland Water

Gable Cottage is in the picturesque village of Braunston-in-Rutland. A unique two bedroom cottage annexe, with bath and shower. Dining room with kitchenette (air fryer, microwave, toaster, kettle), and cute gallery sitting area overlooking it. Breakfast welcome pack included, we make our own bread! Access via private lane, parking for 2 cars. We also have an electric car charger Children over 10 welcome, no pets. Discount of £30 a night if only want one bedroom - message us before booking.

Top guest favourite
The image showcases the exterior of Castle Garden Cottage, featuring red brick and whitewashed walls. A gravel path leads up to the entrance, framed by window boxes filled with flowers. The garden area displays lush greenery and is bordered by trees, providing a serene environment.
Cottage
4.96 out of 5 average rating, 167 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, is located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

Top guest favourite
Cabin
5 out of 5 average rating, 226 reviews

The Fuller's Shed All Weather Private Hot Tub

Adults only. 2 guests max. Sorry, No pets This cosy lodge offers a romantic haven for couples wanting to relax in peace. The luxury interior is styled to impress with every comfort catered for. Outside the covered veranda has a private hot tub, swing seat, outdoor hot shower and dining area where you can kick back and relax. Whether you want to stargaze, ramble, or relax, this is the ideal quiet venue with stunning sunsets and views over rolling countryside, horses, sheep and alpacas.

Guest favourite
A grassy outdoor space is bordered by neat hedges, contrasting with the lush green hills in the background. The bright sky features scattered clouds, enhancing the tranquility of the rural setting.
Tiny home
4.84 out of 5 average rating, 327 reviews

Lower Farm View - Perfect For 2

Lower Farm View is beautifully converted with outstanding views, it's situated in the Rutland Village of Empingham and is only a short walk from Rutland Water's North Shore. Only 6 miles from the beautiful Georgian town of Stamford and 6/7 miles from the picturesque towns of Uppingham and Oakham. The village itself has a hairdresser, doctor's surgery, pub and shop. The local area has lots of pubs, cafes and shops. A perfect place to be able to enjoy and explore the county of Rutland.

Top guest favourite
A charming garden is illuminated by soft lights, showcasing a path leading to a thatched-roof building. The well-maintained green space features neatly arranged plants and shrubs, with a birdbath as a focal point. The atmosphere suggests a tranquil evening setting.
Home
4.96 out of 5 average rating, 424 reviews

Oak Tree Annexe

Oak Tree Annexe is set in a secluded and secure walled garden. You can park for free directly outside the house and will be staying in one of Rutland’s most desirable villages. Set on the fabulous cycle route around the water and with access to great walks directly from the house or a short drive away it’s a perfect location for exploring Rutland. Our village pub is a 3 minute stroll, serves food 7 days a week and offers our guests a 10% discount on their meals.

Top guest favourite
A charming townhouse exterior is framed by neatly trimmed hedges, providing privacy. A light blue front door serves as a focal point, flanked by windows with shutters. Satellite dishes are mounted on the façade, enhancing the contemporary feel of the historic brick structure.
Townhouse
4.95 out of 5 average rating, 358 reviews

Fennel House. Charming house in Oakham town centre

The townhouse is located on a quiet residential one way street. Oakham has stunning historical architecture, i.e a castle, quaint independent shops, pubs and restaurants are moments from the door. A short walk from the railway station. It is ideal for couples or families. A short drive is Rutland Water and is the largest man made lake in Europe 26 miles circumference and hosts many outdoor pursuits such as walking, cycling and bird watching.

Top guest favourite
The living area features a decorated mantel adorned with warm white lights and greenery. A mirror reflects soft illumination, while a cozy dining table is visible in the background. A bookshelf filled with various books complements the inviting atmosphere.
Townhouse
5 out of 5 average rating, 88 reviews

Cozy Nook Boutique Cottage

Due to the huge success of Honeysuckle House my other holiday home in Oakham I have added Cozy Nook, an easy 10 minute walk from Oakham train station and Oakham High street with its many cafes and restaurants. Enjoy everything Oakham has to offer, spend your days discovering the surrounding area as there are many things to see and do nearby. Cozy Nook is a perfect hideaway for relaxing and exploring our beautiful county of Rutland.

Top guest favourite
Cottage
4.96 out of 5 average rating, 27 reviews

Rutland, Outdoor Copper Bath & Cosy Log Burner

Nestled in the picturesque village of Edith Weston, this cottage boasts a courtyard with a outdoor copper bath, two cosy bedrooms, a comfortable living and dining area, and a fully equipped kitchen. Just a short stroll from the beautiful Rutland Water, it’s the ideal getaway for nature enthusiasts and anyone looking for some peace and quiet ,all while being close to various local attractions and towns. Insta: @theoldforge_rutland

Popular amenities for Oakham holiday rentals

When is the best time to visit Oakham?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Oakham?

    Oakham has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Oakham?

    Experience the best of Oakham with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Oakham?

    Four-legged friends are welcome in Oakham. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oakham?

    Yes! Work meets play with ease at over 20 vacation rentals in Oakham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Oakham have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Oakham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakham have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Oakham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakham have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Oakham. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Oakham?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  1. Airbnb
  2. United Kingdom
  3. England
  4. Rutland
  5. Oakham