
Cottage vacation rentals in Oakham
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Top-rated cottage rentals in Oakham
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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.

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.

Spacious, character cottage in village location
Located in a small village with beautiful countryside views, this spacious, 150 year old character cottage is self-contained with a garden to the front and a courtyard to the rear. It has two bedrooms, a newly refurbished bathroom, beamed living room and spacious kitchen diner. The cottage is 7 miles north of Melton Mowbray on the Notts / Leics border. Originally converted from a barn in the 1850s, it has been recently refurbished to a high standard but still retains many original features.

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.

Hardwick Lodge Barn - Guest House in Rural Setting
Hardwick Lodge Barn is a beautifully converted barn blending contemporary style with rustic charm. Nestled in a rural location, it offers a tranquil retreat surrounded by picturesque countryside. Polished concrete floors and bi-folding doors provide natural light and openness, while original oak beams add character. Relax by the log burner or explore Northamptonshire's beauty. Designed for comfort and style, the Hardwick Lodge Barn is ideal for a rural escape with modern amenities.

Daphne's cottage
Our comfortable self-contained cosy dwelling of traditional build located in a rural village just North of Stamford. A stone throw away from the A1 leading you to points of attraction such as Stamford, a beautiful historic town center. Rutland water, "the largest man made lake in the UK" that is perfect for outdoor activities. Belton Estate, part of the National trust. Keen cyclists are able to store their bicycles safely away in our key lock garage (subject to pre-arrangment)

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.

School Cottage - Cosy 1 bedroom Country Cottage
A cosy mid terraced 1 bedroomed cottage in the small village of Ewerby, near Sleaford. Ideally situated for weddings, sight seeing, or a romantic break in the country. The cottage features an open plan lounge & kitchen with log burner, smart TV, cooker, fridge/freezer & microwave. Winding stairs lead up to the luxurious & cosy bedroom with a standard double bed & en-suite shower room. This is a non smoking cottage & parking is on the street in this safe & peaceful village.

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.

Lovely cottage in outstanding rural location.
Self contained accommodation, private entrance in beautiful rural setting. Sitting room with log burner and kitchen with oven, fridge, microwave and Nespresso machine. Two bedrooms with shared bath / shower room. We allow up to 2 dogs. We also offer a fully enclosed half acre paddock for exercising them. No street lights so it is a perfect location for stargazing. Village pub 5 mins walk away. Local for Stamford, Belvoir Castle, and Burghley House.

Number 4, Pleasant Terrace, Uppingham, Rutland
No.4 is close to the centre of Uppingham. You’ll love No.4 because of the views over open countryside at the back whilst being within a 5 minute walk of the towns restaurants and pubs. No.4 is good for couples and business travellers. Parking is unrestricted on the road outside. Pleasant Terrace is a Cul-De-Sac so no passing traffic and it is very quiet and peaceful at night.
Popular amenities for Oakham cottage rentals
Cottage rentals with a hot tub

Oak Cottage, optional hot tub.

Pitcher's Off Grid Barn with Log Burner & Hot Tub

In the ❤️ of Sherwood Forest, cosy cottage for 12

Country cottage with log burner & hot tub

Modern house in countryside setting with hot tub!

Lime Tree Cottage new barn convention

The Old Coach House, Wheatsheaf Mews

Hastings Retreat Parlour barn with private lake
Pet-friendly cottage rentals

The Wood Shed

One bedroom boutique cottage NEW refurb with views

The secret Cottage on Kimbolton high street

Pepper Cottage- pet-friendly, stylish & cosy

The Hen House

Quiet hideaway in Matlock with far reaching views

Quaint 2 bed cottage, ideally located for walking

Old English Cottage in Chipping Warden
Private cottage rentals

Beautiful view from cosy cottage with sunny garden

Lovely cottage in Oakham-a calm and relaxing oasis

The Cart Barn Ground Level Farm Stay Warwickshire

Barn conversion set in 30 acres of nature reserve.

Cosy 1700s period cottage, open fire & king bed

A beautiful cottage in the Vale of Belvoir

The Forge @ Alderwasley

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

Nightly prices starting at
Oakham vacation rentals start at ﺩ.ﺇ624 per night before taxes and fees

Verified guest reviews
Over 250 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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- Silverstone Circuit
- Bletchley Park
- Woburn Safari Park
- Burghley House
- Lincoln Castle
- Sundown Adventureland
- Coventry Cathedral
- Wicksteed Park
- Cambridge University Botanic Garden
- Gulliver's Land Theme Park Resort
- Woodhall Spa Golf Club
- Kettle's Yard
- The Nottinghamshire Golf & Country Club
- Aqua Park Rutland
- Rufford Park Golf and Country Club
- The Fitzwilliam Museum
- Derwent Valley Mills
- Leamington & County Golf Club
- National Justice Museum
- Bosworth Battlefield Heritage Centre
- Stanwick Lakes




