
Cottage vacation rentals in Oakham
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Top-rated cottage rentals in Oakham
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Linseed Barn by Stamford Holiday Cottages
Relax in this luxury barn conversion with views across open fields towards Burghley House, just minutes from Stamford. This two-bedroom cottage is ideal for two couples or a family of four. The open-plan kitchen and living space has a log burner, comfortable seating and dining space. Full-width bifold doors open onto the garden. Guests can also enjoy The Dutch Barn Wellbeing on site, offering yoga, fitness classes and treatments. Flexible bed configurations, two bathrooms and a cot available.

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.

Hot tub 4 bed RURAL Cottage sleeps 8 nr Stamford
Free hot tub Sleeps 8 in 4 double bedrooms Free logs for open fire Comado grill £10 2 Dogs welcome (mostly fenced garden) Linens and towels Oak framed dining room Free welcome hamper Free continental breakfast Late checkout available (£28 -£50) Close to Irnham Hall & The Grange Wedding Venues Country Walks/ Cycling From front door Cosy traditional pub in next village board games, jigsaws, play room & Netflix We are 12 mins from A1 so good location for meeting up Free Wifi.

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.

The Barn
The Barn is a rural retreat tucked away at the end of a quiet leafy lane in Colston Bassett in the heart of the beautiful Vale of Belvoir. Ideal for families, walkers, cyclists, gastro enthusiasts or perhaps those just looking to enjoy the peace and quiet of the countryside, The Barn is a brand new, hand-crafted home built by the architect owner who lives in The Old Farmhouse next door. We also welcome well behaved dogs (we just request a modest fee of £20 per dog per stay)

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

Rural cottage with hot tub near Newark on Trent

The Cottage at Two Back Lane

Pitcher's Barn with Covered Hot Tub & Log Burner

Hollies cottage

Country cottage with private hot tub & log burner

Lime Tree Cottage new barn convention

Church Farm Cottage South Hykeham Lincoln

The Old Coach House, Wheatsheaf Mews
Pet-friendly cottage rentals

The Bramley Nook

Cosy cottage in city centre with free parking

One bedroom converted dairy in Willoughby

Stunning Farm Cottage in tranquil rural setting

Grade II listed holiday cottage with Log burner

Self-contained coach house in peaceful location

NEW* Country Cottage with log fire & parking

The Machinery Shed
Private cottage rentals

Darley Abbey Mills Cottage

Hunky Dory Cottage

Wheelwright's Cottage

Our Cosy Cottage of Hearts ♥️

Charming country cottage in quiet rural setting

A beautiful cottage in the Vale of Belvoir

The Bull Pen - Barn conversion 3 Ensuite bedrooms

Stunning lodge in idyllic setting, near Cambridge
Quick stats about cottage rentals in Oakham

Nightly prices starting at
Oakham vacation rentals start at G$39,745 GYD 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!
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