
Cottage holiday rentals in Oakham
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Top-rated cottage rentals in Oakham
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Pitcher's Barn with Covered Hot Tub & Log Burner
Charming barn conversion with a relaxing hot tub and a warm, inviting log burner, perfect for a countryside retreat. Situated on our 350 acre Farm in the Northamptonshire Uplands Only a 20 minute Taxi from Market Harborough and Rugby Train Stations. Both on London Lines It has Fantastic country-side views with local amenities within walking distance. Remote, private, and homely with all modern comforts to be the perfect getaway to the country And to top it off it is a Carbon Neutral Property

Charming 2-bed cottage in beautiful location
Bay Tree Cottage is a delightful, cosy & private retreat, centrally located with easy access by road or train (M1, M6, A14). You have the entire cottage to yourself with private off road parking for 3 cars & private front & rear gardens. Fully equipped kitchen with dining area & Utility room. Living room with 60" TV, Sky, DVD & log burner. Bathroom with shower & entrance Hall 1st floor: Main bedroom - King size bed & 50"TV, Second bedroom with Double Bed & Wardrobe, Bathroom with Roll top bath.

Pea Cottage - A beautiful countryside retreat
Pea Cottage is a secretive, luxury cottage full of surprises. You're getting more than just a gorgeous place to hang out; the host has lined up a thoughtful selection of extras to make the most of your romantic break. These include a Prosecco Treasure Hunt, use of a tandem, an old fashioned record player, homemade "Scrum-Pea Cider", a choice of two walks and three hand-picked pubs to enjoy a memorable meal. Pea Cottage is 5 miles from Stamford, one of the prettiest market towns in the country.

NEW Luxury Romantic Cottage - Idyllic Rural Bliss
Brand New! Beautiful Romantic Country Cottage with private deck offering amazing rolling countryside views set on 14 acre estate. • Blissful tranquillity • Easy Access to A14, M1 & M6. • 10 mins to Market Harborough • Super King wide bed - Can split to 2 singles • Sofa bed - 1 adult or 2 kids Enjoy: • Fully Equipped Kitchen • 100MB Fibre Internet • Gas BBQ • Original Art • Luxury Linens • FREE Netflix, Disney+ & Xbox • Amazon Echo + Free Music • Air Conditioning + Underfloor Heating

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!

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.

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.

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.

Willow Cottage
The accommodation was once a barn dating back to 1900. It is a contemporary conversion within the rear garden of the main house. The property incorporates everything needed for a great stay. It is completely private and self-contained. The ground floor consists of an open plan living room/kitchen and is accessed by two large patio doors. A staircase leads to a light and airy bedroom with a king size bed, drawers and a wardrobe. There is an en-suite bathroom with walk-in shower.

Beautiful Grade II Listed Barn Conversion
A beautiful Grade II listed stone barn with traditional & period features, but with all modern amenities. Comprised of 2 bedrooms & 2 bathrooms: one double-bed ensuite & a twin room. A traditional & well-equipped kitchen (inc washing machine & dishwasher). Flatscreen TV/DVD & Wifi. Access to own patio area with BBQ. Central heating and double glazing throughout. Parking outside the property with access to an electric charging point. Well behaved dogs (2 maximum) are welcome.

Idyllic Thatched Country Cottage - a hidden gem!
Situated in the picturesque village of Wing, this adorable thatched cottage is nestled in the grounds of beautiful Cedar House. The property was fully renovated in March 2021 and is the ideal getaway location to explore everything that stunning Rutland has to offer. The cottage is only 5 minute drive to Rutland Water, Uppingham and Oakham, so you have everything you wish to experience during your stay on your doorstep. Historic Stamford is also only 20 mins away.

Pantiles Cottage, Stretton, sleeps 4 self catering
Beautiful, recently renovated, detached stone cottage. Both bedrooms are en-suite, one with king sized bed the other twin zip and link beds, which can be used as a double if requested. Modern fully fitted kitchen diner and separate lounge. Free Wifi. Owners, Gill and Greg Harker live on site. Car parking for two cars. Stretton is 7 miles from Rutland Water, 8 miles from Oakham and 9 miles from Stamford and Burghley. Electric charging point available.
Popular amenities for cottage rentals in Oakham
Cottage rentals with a hot tub

Sycamore Farmhouse

Rural cottage with hot tub near Newark on Trent

The Cottage at Two Back Lane

Hollies cottage

Country cottage with private hot tub & log burner

Modern house in countryside setting with hot tub!

Acorn Cottage - couples escape

Church Farm Cottage South Hykeham Lincoln
Pet-friendly cottage rentals

Suttons Cottage in the Heart of Charnwood Forest

Cosy cottage in city centre with free parking

Grade II listed holiday cottage with Log burner

Cosy Modern Pretty Country Cottage

Lovely listed cottage in old centre with garden.

NEW* Country Cottage with log fire & parking

Town Centre Cottage in Stamford

The Reading Room
Private cottage rentals

Rutland, Outdoor Copper Bath & Cosy Log Burner

Cosy & Quirky Cottage Retreat

Lovely cottage in Oakham-a calm and relaxing oasis

Wheelwright's Cottage

Linseed Barn by Stamford Holiday Cottages

The Coach House at the Grange

Stunning lodge in idyllic setting, near Cambridge

Braunston Manor Cottage: 4-poster beds & ensuites
Quick stats about cottage rentals in Oakham

Nightly prices starting at
Oakham holiday rentals start at $245 SGD per night before taxes and fees

Verified guest reviews
Over 290 verified reviews to help you choose

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
- Lincoln Castle
- Woburn Safari Park
- The National Bowl
- Burghley House
- University of Warwick
- Donington Park Circuit
- National Exhibition Centre
- Coventry Cathedral
- Cambridge University Botanic Garden
- Wicksteed Park
- Coventry Building Society Arena
- Gulliver's Land Theme Park Resort
- University of Cambridge
- Santa Pod Raceway
- Kettle's Yard
- Warwick Castle
- National Justice Museum
- Sundown Adventureland
- Belvoir Castle
- Resorts World Arena
- Southwell Minster





