Cottage vacation rentals in Oakham

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Top-rated cottage rentals in Oakham

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Guest favorite
The open-plan living space displays a light and airy atmosphere, featuring high vaulted ceilings and multiple skylights. Comfortable seating is arranged around a coffee table, while a dining table for six stands nearby. The kitchen offers modern appliances, and a warm log burner is positioned beside the seating area.
Cottage in Lincolnshire
4.96 out of 5 average rating, 102 reviews

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.

Top guest favorite
A cozy bedroom features a spacious bed with a cushioned headboard against a backdrop of warm stone walls. Natural light enters through a small window, complemented by soft fabric curtains. The wooden floor enhances the room's inviting ambiance.
Cottage in Stamford
4.95 out of 5 average rating, 355 reviews

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.

Guest favorite
The country cottage is set on a spacious estate, surrounded by rolling green fields. The brick structure features a welcoming entrance with a covered porch and two dormer windows. A well-maintained, paved courtyard emphasizes the home's secluded and tranquil setting.
Cottage in Northamptonshire
4.96 out of 5 average rating, 392 reviews

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

Top guest favorite
A pathway is lined with lavender plants leading up to the Barn, which is framed by greenery and trees. The stone structure features large, inviting windows that open onto the garden, enhancing the serene countryside setting.
Cottage in Stoke Albany
5 out of 5 average rating, 212 reviews

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.

Top guest favorite
The image captures a serene village scene, featuring charming stone cottages nestled among lush greenery. The majestic church tower rises in the background, adding architectural interest. A pathway winds gently through the area, inviting exploration of the picturesque surroundings.
Cottage in Ketton
4.95 out of 5 average rating, 156 reviews

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!

Top guest favorite
A charming stone exterior of the cottage is visible, featuring several windows complementing the rustic facade. Flower pots with greenery are arranged along a gravel pathway, while a small bench provides a resting spot. Sunlight brightens the area, enhancing the inviting ambiance.
Cottage in Braunston-In-Rutland
4.93 out of 5 average rating, 100 reviews

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.

Top guest favorite
The image showcases the exterior of Castle Garden Cottage, featuring red brick and whitewashed walls. A gravel path leads up to the entrance, framed by window boxes filled with flowers. The garden area displays lush greenery and is bordered by trees, providing a serene environment.
Cottage in Rutland
4.96 out of 5 average rating, 165 reviews

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.

Guest favorite
Cottage in Bulby
4.85 out of 5 average rating, 170 reviews

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.

Top guest favorite
The exterior of a stone barn conversion features a distinct pitched roof and a charming facade. The building is marked by weathered stonework and traditional details, including a chimney and a welcoming entrance, set against a clear blue sky.
Cottage in Empingham
4.99 out of 5 average rating, 185 reviews

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.

Top guest favorite
The exterior of The Barn showcases a combination of brick and wood materials, created in a contemporary style. Large glass doors open to the garden, while a balcony overlooks the rear area. A chimney and various windows enhance the building's rustic charm.
Cottage in Colston Bassett
5 out of 5 average rating, 118 reviews

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)

Top guest favorite
A spacious kitchen features exposed wooden beams and stone flooring. A dining table with striped tableware is set for four, while modern appliances are arranged across the counters. Natural light floods in through multiple windows, illuminating the well-equipped cooking area.
Cottage in Duddington
4.99 out of 5 average rating, 248 reviews

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.

Top guest favorite
A charming thatched cottage exterior is framed by a gravel drive and manicured greenery. Large windows allow natural light to fill the interior, while a subtle mix of stone and thatched roofing contributes to the cottage's historic character.
Cottage in Wing
4.87 out of 5 average rating, 341 reviews

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

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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