Holiday Rentals in Oakham

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Oakham holiday rentals
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Best Holiday rentals and Airbnb offers in Oakham

Discover Central Holiday Rentals in Oakham

Reconnect deeply with your significant other at peaceful holiday rentals for couples in Oakham, offering romantic, quiet settings.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Oakham
10 2 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
The Hideout, a first-floor apartment in Oakham, Rutland, offers convenient access to Oakham Castle and the Rutland County Museum, a short walk from the town centre and within easy reach of Rutland Water.
This 105 square metre self-catering property features two bedrooms sleeping four, a well-equipped kitchen with integrated appliances including a dishwasher, and a modern shower room; Wednesday and Saturday markets provide access to local produce.
Kings Retreat - Oakham
9.5 49 reviews

Kings Retreat

apartment
This charming cottage is located in Oakham, a historic market town in Rutland, just 3 kilometres from Rutland Water. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage offers a spacious living area for up to 6 guests and features a well-equipped kitchen with a dishwasher. Guests can enjoy a private garden, bike hire, and easy access to the town centre, Rutland Water, and the surrounding countryside.
The Hideout - Oakham
9.3 13 reviews

The Hideout

apartment, Oakham
The Hideout is located in Oakham, a market town in Rutland, 39 kilometres from Belgrave Road and 40 kilometres from the University of Leicester.
This two-bedroom apartment, spanning 105 square metres, offers a fully equipped kitchen, a private garden, and a fireplace, comfortably accommodating up to seven guests.
Rooms @ Number Six - Oakham
9.4 435 reviews

Rooms @ Number Six

apartment, Oakham
Rooms @ Number Six is situated in Oakham, a short distance from the town centre and conveniently located 20 miles from Leicester Train Station and Belgrave Road. The apartment has received excellent ratings for cleanliness, location, and user experience.
The apartment has one bedroom and one bathroom, comfortably accommodating two guests. Guests can enjoy a peaceful and secluded atmosphere with views of the private courtyard, free Wi-Fi, a comfortable living area with a flat-screen TV, a well-equipped kitchenette, and daily breakfast options.

Best Oakham holiday rentals with air conditioning

The Den, Pudding Bag Cottage - Oakham
10 36 reviews

The Den, Pudding Bag Cottage

house
The Den studio, a self-contained apartment near Exton village, Rutland, enjoys proximity to 22.5km of parkland and is within walking distance of Hambleton Bakery.
This excellently rated one-bedroom unit sleeps two guests and features a fully equipped kitchen with a Ninja Air fryer, complimentary tea and coffee, and parking, all within a peaceful village setting near the Fox & Hounds pub.

Frequently asked questions about holiday rentals in Oakham

  • What are some interesting places to visit in or near Oakham?

    Oakham Castle is a must-see, with its impressive gatehouse and collection of historic carriages. For a day out exploring nature, head to Rutland Water, a large reservoir with walking trails and watersports. The nearby town of Stamford is also worth a visit, with its charming cobbled streets and historic buildings.
  • What are the best Airbnb and holiday rentals in Oakham?

  • Which walking or cycling routes are the best in Oakham?

    The Rutland Water Nature Reserve offers a variety of walking trails, from gentle strolls to challenging hikes. The Oakham to Melton Mowbray cycle route is a popular choice, taking you through picturesque countryside. The nearby Leicestershire Round is a 100-mile circular route, perfect for experienced cyclists.
  • What are the most popular Airbnbs in Oakham?

  • What sports or outdoor activites can visitors enjoy in and around Oakham?

    Rutland Water is a great spot for watersports like sailing, windsurfing, and kayaking. You can also go fishing, or simply enjoy a picnic by the water. There are several golf courses in the area, and the countryside is ideal for walking, cycling, and horse riding.
  • What are the best holiday rentals with a pool in Oakham?

  • What other towns or cities can be easily accessed from Oakham?

    Oakham is well-connected by road and rail, making it easy to explore other parts of the region. You can easily reach Stamford, Melton Mowbray, Leicester, and Peterborough by car or train. The city of Nottingham is also within a reasonable distance, offering a wide range of attractions.
  • What are the best rentals for families and kids in Oakham?

    The best rentals for families and kids in Oakham are Rutland View, The Gallery Two Bedroom Apartment and Lazy Nest Is A Lazy Comfortable Nest To Laze.

  • What amenities are commonly available in vacation rentals in Oakham?

    Vacation rentals in Oakham typically offer amenities such as Wi-Fi, a kitchen, and laundry facilities. Many also have a garden or patio, and some even have a hot tub or swimming pool. Be sure to check the listing for specific amenities.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakham?

  • What time of year is best to rent a vacation rental Oakham?

    Oakham is a lovely destination year-round. Spring and autumn offer mild weather and beautiful scenery, while summer is ideal for enjoying outdoor activities. If you're looking for a quieter experience, consider visiting during the shoulder seasons.
  • What are the local dishes in Oakham region?

    The local cuisine is hearty and traditional, with dishes like Melton Mowbray pork pies, Stilton cheese, and Leicestershire oatcakes. You can also find plenty of pubs serving classic British fare, such as fish and chips and roast dinners. For something a bit different, try a local delicacy called 'Rutland pudding', a sweet bread pudding with a rich history.

Popular destinations

Choose the Right Holiday Rentals with a Balcony in Oakham

A terrace with city skyline views is a fantastic reason to book a holiday rental in Oakham. View our top picks and start comparing now.

Modern Peaceful Open Plan 1-bed Apartment Rutland - Oakham
No reviews

Modern Peaceful Open Plan 1-bed Apartment Rutland

apartment, Rutland
This Oakham apartment, situated within 10 kilometres of Rutland Water Nature Reserve, Rutland Water Golf Course, and Normanton Church, offers a peaceful retreat in the heart of Rutland.
The 40 square metre self-catering flat features one bedroom, one bathroom, a private balcony, and parking, comfortably accommodating two guests and including amenities such as a fully equipped kitchen and washing machine.
Beautiful Georgian Cottage Within A Private Walled Garden - Oakham
9.1 55 reviews

Beautiful Georgian Cottage Within A Private Walled Garden

house, Oakham
This Georgian cottage in Oakham provides secluded accommodation within a private walled garden, conveniently located approximately 32-34km from Leicester's universities, railway station, and Belgrave Road.
The three-bedroom property sleeps up to 11 guests, boasting a fully equipped kitchen with dishwasher, a terrace, garden, parking, and free Wi-Fi; nearby attractions include Trent Bridge Cricket Ground and Kelmarsh Hall, both around 45km away.
Rutland View - Oakham
9.3 142 reviews

Rutland View

house, Oakham
Rutland View is a spacious holiday home located in Oakham, just 24 miles from Leicester Train Station and 34 miles from East Midlands Airport, offering a peaceful escape in a quiet location. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
Rutland View has 4 bedrooms and 2 bathrooms, providing comfortable accommodation for up to 8 guests across 200 square metres. Guests can enjoy a fully equipped kitchen, a private garden with a terrace, and access to a tennis court, as well as free parking and Wi-Fi.
Moorhen At Exton Park, Rutland - Dog Friendly - Oakham
No reviews

Moorhen At Exton Park, Rutland - Dog Friendly

cabin, Exton
This luxury safari tent, part of Exton Park's walled garden in Rutland, offers a tranquil escape less than 3km from Rutland Water and 20 minutes from Peterborough.
Sleeping up to six guests in three bedrooms, this off-grid retreat boasts a fully plumbed shower room, wood-burning stove, and proximity to Oakham Castle and Rutland Open Air Theatre.

Popular Family-Friendly Holiday Rentals in Oakham

Getting the holiday rental right makes all the difference for a family trip to Oakham. Find city attractions within easy reach. Start comparing now.

Fennel Folly Apartment - Oakham
9.7 38 reviews

Fennel Folly Apartment

apartment
Fennel Folly is a self-catering apartment located in Manton, Rutland, just 5km from Oakham and Uppingham, offering a peaceful and secluded setting in the grounds of Broccoli Bottom. This apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment features two bedrooms, accommodating up to four guests, with an open-plan living, dining, and kitchen area. It boasts a private balcony for outdoor dining, a fully equipped kitchen, and a garden, making it ideal for families or groups of friends. Guests can enjoy walking trails, water sports, and stunning views at Rutland Water, which is within walking distance.
Rutland Hall Lakeside Lodges - Oakham
8.3 52 reviews

Rutland Hall Lakeside Lodges

house, Oakham
Rutland Hall Lakeside Lodges are located in Oakham, just 43 kilometres from Leicester Train Station and Belgrave Road, offering a tranquil escape by Rutland Water. The lodges have received consistently high ratings for cleanliness, location, and overall experience.
These modern lodges feature fully equipped kitchens with fridges, dishwashers, and ovens, allowing guests to prepare their own meals. Guests can enjoy a range of on-site amenities including a fitness centre, indoor swimming pool, garden, terrace, restaurant, and bar, as well as free Wi-Fi and private parking.
A Characterful Home In Oakham - Oakham
9.4 34 reviews

A Characterful Home In Oakham

apartment
Three Dozen, a centrally located Rutland house in Oakham, is a 5-minute walk from Oakham's high street and close to Oakham Castle.
This three-bedroom, one-bathroom property sleeps five, features a kitchen, internet access, and is pet-friendly (confirmation required), offering easy access to Cutts Close playpark and the Castle Grounds.
Beautiful Grade Ii Listed, Fully Renovated Cottage - Oakham
10 13 reviews

Beautiful Grade Ii Listed, Fully Renovated Cottage

apartment
Finches Cottage, a three-bedroom house, is situated on the outskirts of Egleton, Rutland, approximately a few kilometres from Rutland Water, offering easy access to watersports and outdoor activities.
This fully renovated property sleeps six, boasting a John Lewis kitchen, enclosed garden with BBQ (high season), log burner (winter months), and pet-friendly features including wicker beds and blankets; nearby dog-friendly pubs add to its appeal.

Handpicked Self-Catering Rentals with Parking in Oakham

Park up and enjoy the city centre. These holiday rentals in Oakham come with a free car park on-site. Start comparing now.

Cosy Contryside Annex - Oakham
10 15 reviews

Cosy Contryside Annex

apartment
10 Pudding Bag Lane - Oakham
No reviews

10 Pudding Bag Lane

house, Exton
The Silvan Lodge
Peace, Privacy, And Pure Calm - Oakham
10 28 reviews

The Silvan Lodge Peace, Privacy, And Pure Calm

apartment
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Oakham
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Empingham

Compare Luxury Holiday Rentals in Oakham

Comfort, quality, and a prime location - each luxury holiday rental or Airbnb in Oakham is selected with these standards in mind. Pick your favourite today.

Buckingham House - Oakham
9.0 2 reviews

Buckingham House

house, Oakham

Explore Pet-Friendly Holiday Rentals in Oakham

Travelling with a pet to Oakham is easy when your holiday rental is properly set up with nearby dog parks and city walks.

10 Pudding Bag Lane - Oakham
9.7 6 reviews

10 Pudding Bag Lane

apartment
Coot - Exton Park - Oakham
No reviews

Coot - Exton Park

house, Exton
5* Gold Beautiful Thatched Chocolate Box Cottage - Oakham
9.9 28 reviews

5* Gold Beautiful Thatched Chocolate Box Cottage

apartment
Brooke - Oakham
No reviews

Brooke

house, Oakham

Find the Best Holiday Rentals with a Pool in Oakham

Having a pool at your holiday rental in Oakham opens up a proper swim in the heart of the city without extra planning. Start comparing.

Maple Lodge, Family Friendly, With Pool In Greetham, Rutland - Oakham
No reviews

Maple Lodge, Family Friendly, With Pool In Greetham, Rutland

cottage, Oakham
Cottesmore Lodge - Oakham
9.5 22 reviews

Cottesmore Lodge

cabin
Burley Lodge - Oakham
8.8 12 reviews

Burley Lodge

cabin
Willow Lodge - Oakham
9.4 143 reviews

Willow Lodge

house, Oakham

Check Out Holiday Rentals with a Hot Tub in Oakham

Private hot tub access after a day in the city is one of those details that makes a trip to Oakham truly memorable.

Luxury, In The Heart Of Rutland. A Home For All Occasions - Oakham
10 5 reviews

Luxury, In The Heart Of Rutland. A Home For All Occasions

apartment, Ketton
Shepherd's Hut With Wood-fired Hot Tub And Epic Views Over Rutland Water - Oakham
No reviews

Shepherd's Hut With Wood-fired Hot Tub And Epic Views Over Rutland Water

cabin, Rutland
Luxury Rural Barn With Hot Tub And Log Burner - Oakham
9.6 15 reviews

Luxury Rural Barn With Hot Tub And Log Burner

farm
Buckingham House, Pet Friendly, With Hot Tub In Whissendine - Oakham
No reviews

Buckingham House, Pet Friendly, With Hot Tub In Whissendine

cottage, Oakham
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