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Cottage holiday rentals in Oakham

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Quick stats about cottage rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at $181 AUD per night before taxes and fees

  • Verified guest reviews

    Over 330 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!

Top-rated cottage rentals in Oakham

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a charming 17th-century cottage is featured, showcasing a thatched roof and white-washed walls. Surrounded by greenery, the cottage has large windows with gray frames, and a gravel pathway leads to the entrance, enhancing its quaint appeal.
Cottage in Cottesmore

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.

FamilyLocationLayout

4.98 out of 5 average rating, 141 reviews
Superhost
Cottage in Bulby

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 The Grange Wedding Venue Travel Cot available 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.

LocationFamilyTV

4.85 out of 5 average rating, 176 reviews
Guest favourite
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

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!

LocationValueTV

4.94 out of 5 average rating, 166 reviews
Top Guest favourite
A charming cottage exterior showcases a brick and stone facade, framed by colorful flowering plants. Sunlight bathes the entrance, which features a wooden canopy. Windows offer glimpses into the interior, surrounded by a well-maintained garden with vibrant blooms.
Cottage in Upper Broughton

Beautiful 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.

LocationFamilyIndoor spaces

4.99 out of 5 average rating, 175 reviews
Top Guest favourite
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 Oakham

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.

LocationFamilyNearby

4.96 out of 5 average rating, 179 reviews
Top Guest favourite
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

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.

LocationFamilyComfort

4.99 out of 5 average rating, 195 reviews
Guest favourite
A private patio area features a circular stone surface, accompanied by two metal chairs. The brick exterior of the contemporary conversion is visible, with large patio doors leading into the living space. Lush greenery surrounds the garden, enhancing the tranquil setting.
Cottage in Harborough

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.

LocationFamilyBreakfast

4.95 out of 5 average rating, 214 reviews
Top Guest favourite
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

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)

LocationValueBarbecue

5.0 out of 5 average rating, 128 reviews
Top Guest favourite
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

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.

FamilyLocationWi-Fi

4.99 out of 5 average rating, 253 reviews
Guest favourite
A charming stone cottage with a red-tiled roof is surrounded by greenery. Large windows allow natural light to enter, while a small patio area with two metal chairs and potted plants sits in the foreground. The entrance features a dark wooden door.
Cottage in Rutland

Pantiles Cottage, Stretton, sleeps 4 self catering

Beautiful, renovated, detached stone cottage. Both bedrooms en-suite, one with king sized bed the other twin zip and link beds, Modern fully fitted kitchen diner and separate lounge. Free Wifi. Owners, Gill and Greg live on site. 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. The White Horse Country Inn is next door, recently renovated and open for bookings.

FamilyLocationIndoor spaces

4.89 out of 5 average rating, 215 reviews
Guest favourite
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

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.

ValueLocationWi-Fi

4.86 out of 5 average rating, 369 reviews
Guest favourite
A spacious courtyard is framed by rustic buildings with red brick and whitewashed walls. Vibrant red foliage climbs the exterior, providing a striking contrast to the greenery. A small seating area with white chairs and a table invites relaxation in this tranquil rural setting.
Cottage in Leicestershire

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.

ValueLocationBathroom

4.92 out of 5 average rating, 456 reviews

Popular amenities for Oakham cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Superhost
Cottage in Thurgarton

Hot Tub, Horses & Hills – The Perfect Escape

FamilyLocationOutdoor spaces

4.93 out of 5 average rating, 99 reviews
Top Guest favourite
Cottage in Husbands Bosworth

Pitchers Barn with Wood Fired Hot Tub & Log Burner

ValueLocationWalkability

4.92 out of 5 average rating, 395 reviews
Guest favourite
Cottage in Upper Broughton

Country cottage with private hot tub & log burner

LocationFamilyHeating

4.9 out of 5 average rating, 106 reviews
Top Guest favourite
A hot tub sits invitingly beneath a cloudy sky, surrounded by softly lit string lights against a trellis. The steam rises gently from the water, suggesting warmth and relaxation in the serene outdoor space.
Cottage in Gosberton

Peaceful cottage in orchard with Hot tub and sauna

FamilyLocationCondition

4.92 out of 5 average rating, 499 reviews
Top Guest favourite
The exterior of the cottage features a charming stone facade with multiple windows. A hot tub sits on the patio beside a shaded dining area under an umbrella, inviting relaxation outdoors. A light-colored tent adds a shaded space near the entrance, enhancing comfort and leisure.
Cottage in Tibshelf

The Old Coach House, Wheatsheaf Mews

LocationValueTV

4.94 out of 5 average rating, 262 reviews
Superhost
A spacious outdoor area features a well-maintained lawn bordered by stone walls. A hot tub is positioned near the back of the space, with seating and decorative plants arranged against the rustic stone exterior of the cottage. Barn and wooden fencing provide additional context.
Cottage in Derbyshire

Croft view cottage

ValueLocationBarbecue

4.88 out of 5 average rating, 358 reviews
Superhost
A spacious living area features two stylish sofas, one in teal and the other in a warm amber hue. Exposed wooden beams adorn the ceiling, while natural light fills the room. A staircase and dining area are visible in the background, enhancing the open layout.
Cottage in Ashby-de-la-Zouch

Hastings Retreat Parlour barn with private lake

FamilyLocationBarbecue

4.91 out of 5 average rating, 181 reviews
Guest favourite
Cottage in Leamington Spa

Tinkers Corner: 1 bedroom cottage, Leamington Spa

FamilyValueNearby

4.92 out of 5 average rating, 106 reviews

Pet-friendly cottage rentals

Top Guest favourite
A bright and airy living area is characterized by high ceilings and exposed wooden beams. A yellow sofa is complemented by blue accent pillows, while a brown armchair adds warmth. A stone floor leads to large windows, bringing in natural light. Decorative art and furnishings enhance the space.
Cottage in Aldwincle

The Old Forge, gorgeous 2 bedroom cottage

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 102 reviews
Top Guest favourite
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

Pea Cottage - A beautiful countryside retreat

FamilyValueQuiet

4.95 out of 5 average rating, 374 reviews
Top Guest favourite
The bathroom features a large copper bath set against exposed brick walls and timber beams. Natural light enters through a skylight and the space is complemented by antique-style decor, with fluffy white bathrobes hanging and decorative framed prints on the walls.
Cottage in Lincoln

Granary Digby, Luxury rural cottage nr Lincoln

ValueLocationComfort

4.99 out of 5 average rating, 379 reviews
Top Guest favourite
The exterior of the coach house features a charming brick facade adorned with lush greenery and climbing plants. Bright white flowers create a contrast against the greenery, while a gravel pathway leads to the front. Several potted plants add to the welcoming appearance.
Cottage in Gumley

Self-contained coach house in peaceful location

FamilyLocationCheck-in

4.96 out of 5 average rating, 238 reviews
Top Guest favourite
A light-filled dining area features a round table surrounded by wooden chairs. A decorative vase filled with flowers sits at the center. A built-in cabinet displays various plates and glassware. Large windows and a glass roof create an airy atmosphere.
Cottage in Haconby

As featured in 25 Beautiful Homes - Cottage for 2

ValueLocationNearby

4.98 out of 5 average rating, 116 reviews
Guest favourite
The charming exterior of a limestone cottage is displayed, featuring traditional stonework and a distinctive red front door. Symmetrical windows with white frames complement the historical architecture, while the sun casts a warm glow over the roof, accentuating its gentle curve.
Cottage in Oundle

Lovely listed cottage in old centre with garden.

ValueLocationParks

4.88 out of 5 average rating, 229 reviews
Top Guest favourite
A cobbled driveway leads to a charming barn conversion, framed by greenery and flowering plants. The red brick exterior showcases the rustic character of the property, with large arched doors and a welcoming entrance to the barn on the left.
Cottage in Monks Kirby

Characterful 2-bed cottage in rural Warwickshire

FamilyValueDecor

4.94 out of 5 average rating, 396 reviews
Guest favourite
The image showcases four views of the cottage. A serene sleeping area features a cozy king bed with fresh linen. The modern kitchen is fully equipped with integrated appliances. A comfortable living space includes a green sofa beside a log burner. The outdoor view presents a peaceful lakeside path.
Cottage in Pitsford

NEW* Country Cottage with log fire & parking

FamilyValueAccess

4.89 out of 5 average rating, 114 reviews

Private cottage rentals

Top Guest favourite
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

Converted Barn overlooking fields.

LocationFamilyLong stay

5.0 out of 5 average rating, 227 reviews
Top Guest favourite
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

Linseed Barn by Stamford Holiday Cottages

FamilyValueIndoor spaces

4.96 out of 5 average rating, 108 reviews
Top Guest favourite
A charming exterior view of the house is framed by large arched windows. Vibrant flower beds, featuring a mix of colors, border a gravel pathway. Outdoor seating is arranged nearby, inviting relaxation in a serene natural setting.
Cottage in North Kilworth

Barn conversion set in 30 acres of nature reserve.

LocationValueIndoor spaces

5.0 out of 5 average rating, 166 reviews
Top Guest favourite
The entrance to the cottage features a light green door set against a textured stone wall. Flanking the door are two decorative planters containing small olive trees, alongside additional pots with greenery, creating a welcoming appearance.
Cottage in Haselbech

Our Cosy Cottage of Hearts ♥️

LocationFamilyParks

4.91 out of 5 average rating, 443 reviews
Top Guest favourite
The exterior of the house is characterized by a red-tiled roof and cream-colored walls, featuring skylights that allow natural light. The design includes large white doors and a small window, framed by a neatly maintained garden area. Surrounding vegetation adds to the rural setting.
Cottage in Lutton

Woodbine Farm: A clean peaceful country retreat

ValueLocationGetting around

5.0 out of 5 average rating, 225 reviews
Guest favourite
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

NEW Luxury Romantic Cottage - Idyllic Rural Bliss

ValueFamilyAccess

4.96 out of 5 average rating, 400 reviews
Top Guest favourite
A charming entryway features an arch adorned with vibrant purple flowers, leading to the inviting facade of the Victorian cottage. The red brick exterior is highlighted by lush greenery, and a spacious lawn can be seen beyond the path.
Cottage in East Haddon

Charming cottage beautiful location + EV charger

LocationValueCleanliness

5.0 out of 5 average rating, 116 reviews
Guest favourite
The exterior of a timber-framed barn is showcased, featuring a traditional red-tiled roof and large black windows. Surrounding greenery and a path lead up to the entrance. The barn’s rustic character is highlighted by weathered wooden beams and a fenced area.
Cottage in Norton Disney

The Reading Room

ValueFamilyBathroom

4.96 out of 5 average rating, 321 reviews

Destinations to explore