
Holiday houses in Oakham
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Top-rated holiday rentals in Oakham
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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

Churchyard Ketton stone cottage next to the pub
Eighteenth century Ketton stone cottage nestled in the churchyard near the CAMRA award-winning and fabulous Railway Inn. Wood burner, three double/twin rooms, White Company bedding, nearby village vineyard & great food scene, Burghley House ten minutes away, Rutland Water three miles away; England's finest stone town,Stamford, ten minutes. Whether you are a group of three couples, a family or a couple wanting a romantic getaway, this is a great blend of a countryside retreat and great fun!

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.

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.

Primrose Hall Holiday Cottage Rutland
Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, pub, medical centre, and an antique shop just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

Clock Cottage Self contained Rutland Rural Retreat
Clock Cottage is a self contained open plan suite located on the ground floor with garden views located within a characterful rural village within a 5 minute drive from Rutland water. The suite is open plan and includes a king sized bed, comfy living area and kitchen, Nespresso coffee machine, freestanding open plan bathtub and separate bathroom and outside dining area. The living area can be used as a family/friends bedroom with the use of a fold out sofa bed. Ideal for a couple.

Comfy Modern APT - Sleeps 4
Located in the centre of the Historic Market Town of Uppingham. Based in is heart of the small county of Rutland. This apartment is a stones throw away to the gorgeous town centre, with markets every Friday, great places to eat and drink and some really cute little shops. A quick 10 minute drive to another Market Town of Oakham and not far from Rutland Water where you can enjoy some beautiful scenic walks. The apartment offers an allocated parking space and communal paved garden.

Central Character/Contemporary Apartment
Set within walking distance to Uppingham’s bustling town centre is this stunning central ground floor apartment full of character and original features creating an ultimate holiday experience. Guests will enjoy two spacious double bedrooms, built in wardrobe, hand crafted breakfast kitchen, exceptional shower room, subtle design touches and beautiful courtyard garden. Free parking is available 2-3min walk away from the property. There is also 2hrs free parking to the front.

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.

Comfortable, well located, converted apartment.
Enjoy a comfortable stay in this recently renovated, centrally located two bedroom apartment. Located just 5 minutes walk from Oakham town centre and with dedicated parking, this apartment is well suited for those looking for a place to stay for either work or pleasure. With Rutland Water just a few minutes away and with direct trains to Birmingham , Stamford and Stansted airport it's a great place to base yourself even when exploring further afield.

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.

Beautiful Conversion in Rutland Countryside
Come and stay in our lovingly converted barn in the middle of the Rutland countryside. Perfect for a quiet get-away with lots of walking and cycling from the doorstep. Set in a 3 acre plot of our family home, you will have access to a private garden at the rear of the property plus our orchard should you wish to bring 1 small - medium sized dog with you. Unfortunately, the property is not suited to large dogs.
Popular amenities for Oakham holiday rentals
Other great holiday rentals in Oakham

Halliday’s Folly - Spacious Cottage with parking

Enclosed garden, footpath walk to Rutland Water

Triple Cottage - Country Stay

The Garden House II at Top View

Independence House - Oakham

Puddle Duck Cottage

Stunning & spacious Georgian town house + parking

Luxurious, entire Blacksmiths Barn in Rutland.
When is the best time to visit Oakham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $207 AUD | $212 AUD | $215 AUD | $259 AUD | $265 AUD | $239 AUD | $201 AUD | $242 AUD | $229 AUD | $207 AUD | $185 AUD | $202 AUD |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Frequently Asked Questions
Are there family-friendly house rentals in Oakham?
Oakham has more than 10 family-friendly house rentals. 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 house rentals with a dedicated workspace in Oakham?
Yes! Work meets play with ease at over 10 house rentals in Oakham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Oakham?
Make yourself at home in Oakham by choosing from our most frequently booked neighborhoods. We have over 100 vacation rentals in Oakham, over 80 vacation rentals in Barleythorpe, and over 80 vacation rentals in Braunston.
Do house rentals in Oakham have a kitchen?
Absolutely! We offer over 10 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.
Quick stats about holiday rentals in Oakham

Total holiday rentals
Explore 40 holiday rentals in Oakham

Nightly prices starting at
Oakham holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 2,000 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Oakham holiday rentals include Wi-Fi 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!
Destinations to explore
- Silverstone Circuit
- Motorpoint Arena Nottingham
- Bletchley Park
- Woburn Safari Park
- Lincoln Castle
- Burghley House
- The National Bowl
- National Exhibition Centre
- Santa Pod Raceway
- Coventry Cathedral
- Cambridge University Botanic Garden
- Wicksteed Park
- Gulliver's Land Theme Park Resort
- University of Warwick
- Donington Park Circuit
- University of Cambridge
- Kettle's Yard
- The Fitzwilliam Museum
- Belvoir Castle
- National Justice Museum
- Resorts World Arena
- Coventry Building Society Arena
- Coventry University
- University of Lincoln




