
Cottage vacation rentals in Oakham
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Oakham vacation rentals start at ﺩ.ﺇ 698 per night before taxes and fees

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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 cottage rentals in Oakham
Guests agree: these cottages are highly rated for location, cleanliness, and more.

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

Quiet Lane Retreat: The Bee Cottage Rutland
Welcome to our charming cottage located on a tranquil lane in Rutland. Just a quick 5-min drive from Rutland Water, this 17th-century cottage is a picture-perfect gem that has undergone a refurbishment. The thatched roof adds to its undeniable charm. Step inside and be greeted by original features like low ceilings, doorways and exposed beams, creating an authentic atmosphere. The cottage comfortably accommodates up to 5 people, offering surprisingly spacious living. Enjoy free Netflix and WiFi.

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

Converted Barn overlooking fields.
Built in 1634, the Barn is on the edge of a village 5m from Market Harborough in Leicestershire. Converted in 2017, it's on our property but separate from it. Light and airy, it's one room/open plan downstairs, with areas for cooking, dining and relaxing. French doors lead out onto a pretty courtyard garden, with stone steps up to a raised area, where you can watch the sunset over the fields. Upstairs there's a well-equipped bedroom and bathroom with far reaching views over the countryside.

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.

Granary Digby, Luxury rural cottage nr Lincoln
Luxury self-catering accommodation on the border of the Lincolnshire limestone heath and the Witham valley. Centrally located at the heart of rural Lincolnshire, and only a 12 mile drive from The city of Lincoln. The Granary is a beautifully converted Lincolnshire barn, bursting with character and the perfect location from which to explore this historic county. Situated on the very edge of the rural village of Digby, the Granary forms one side of the original yard and stables.

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.
Popular amenities for Oakham cottage rentals
Cottage rentals with a hot tub

Sycamore Farmhouse

Rural cottage with hot tub near Newark on Trent

Oak Cottage, optional hot tub.

The Cottage at Two Back Lane

New Lovely cottage in rural Leicestershire hot tub

Country cottage with private hot tub & log burner

Modern house in countryside setting with hot tub!

Lime Tree Cottage new barn convention
Pet-friendly cottage rentals

The Bramley Nook

The Hen House

One bedroom converted dairy in Willoughby

Stunning Farm Cottage in tranquil rural setting

Lovely listed cottage in old centre with garden.

Self-contained coach house in peaceful location

Harrisons Cottage in the Heart of Charnwood Forest

Hardwick Lodge Barn - Guest House in Rural Setting
Private cottage rentals

Darley Abbey Mills Cottage

Rural Retreat set in a conservation area.

Linseed Barn by Stamford Holiday Cottages

Barn conversion set in 30 acres of nature reserve.

Our Cosy Cottage of Hearts ♥️

Cosy 1700s period cottage, open fire & king bed

Stamford - Luxurious & Chic fully equipped cottage

Braunston Manor Cottage: 4-poster beds & ensuites
Destinations to explore
- Silverstone Circuit
- National Exhibition Centre
- The National Bowl
- Donington Park Circuit
- University of Warwick
- Bletchley Park
- Woburn Safari Park
- Lincoln Castle
- Burghley House
- Coventry Building Society Arena
- University of Cambridge
- Motorpoint Arena Nottingham
- Cambridge University Botanic Garden
- Belvoir Castle
- Santa Pod Raceway
- Coventry Cathedral
- Warwick Castle
- Gulliver's Land Theme Park Resort
- Wicksteed Park
- Loughborough University
- Resorts World Arena
- Kettle's Yard
- University of Nottingham
- Southwell Minster





