Holiday rentals with outdoor seating in Oakham

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Top-rated rentals with outdoor seating in Oakham

Guests agree: these rentals with outdoor seating 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
4.98 out of 5 average rating, 135 reviews

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.

Top guest favourite
The image captures a scenic view of a lush countryside landscape, featuring rolling green hills and dense trees. In the center, a charming yellow house is nestled amongst the greenery, surrounded by expansive fields and rich foliage under a partly cloudy blue sky.
Apartment
4.9 out of 5 average rating, 171 reviews

The Hayloft: Popular Hideaway - Sleeps 3.

After our storming success for 6 years with our cosy Hayloft Apartment, we have totally refitted the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking [Now with EV Charging] a private patio for sunny breakfasts, lunches or sundowners. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details. The Welcome pack's a big hit.

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
4.96 out of 5 average rating, 158 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 favourite
Religious building
4.88 out of 5 average rating, 295 reviews

The Chapel

Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" , on TV & won a local design award New for 2025-advanced ai heating system Owners next door COMPLETELY OPEN PLAN Internal walls around Bathroom only.

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
4.99 out of 5 average rating, 177 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 favourite
A comfortable living area features a light-colored sofa with decorative cushions, accompanied by an armchair. A wooden cabinet is displayed against one wall, while a wall-mounted light fixture provides illumination. Large glass doors open to a deck with garden views.
Home
4.97 out of 5 average rating, 115 reviews

The Den self-contained annex.

The Den is a self- contained annex, which is very comfortable for 4 guests. It will provide everything you need for a short or long stay in Melton Mowbray. We provide tea, coffee, bread, milk etc. The property has a fitted kitchen with washing machine and tumble dryer. An open living space leads to two bedrooms with king size beds, & a bathroom with a walk in shower. There is parking for two cars on the drive and plenty of on street parking. Check in is from 3pm, & check out is by 10am.

Guest favourite
An open plan suite features a king-sized bed with a plush headboard, complemented by a decorative quilt. A vintage grey wardrobe stands beside the freestanding bathtub, which is positioned near a large wall clock. Soft lighting enhances the serene atmosphere of the space.
Flat
4.86 out of 5 average rating, 295 reviews

Clock Cottage Self contained Rutland Rural Retreat

Clock Cottage is a self contained open plan suite located on the ground floor with garden views located within a characterful rural village within a 5 minute drive from Rutland water. The suite is open plan and includes a king sized bed, comfy living area and kitchen, Nespresso coffee machine, freestanding open plan bathtub and separate bathroom and outside dining area. The living area can be used as a family/friends bedroom with the use of a fold out sofa bed. Ideal for a couple.

Top guest favourite
A charming garden is illuminated by soft lights, showcasing a path leading to a thatched-roof building. The well-maintained green space features neatly arranged plants and shrubs, with a birdbath as a focal point. The atmosphere suggests a tranquil evening setting.
Home
4.96 out of 5 average rating, 382 reviews

Oak Tree Annexe

Oak Tree Annexe is set in a secluded and secure walled garden. You can park for free directly outside the house and will be staying in one of Rutland’s most desirable villages. Set on the fabulous cycle route around the water and with access to great walks directly from the house or a short drive away it’s a perfect location for exploring Rutland. Our village pub is a 3 minute stroll, serves food 7 days a week and offers our guests a 10% discount on their meals.

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
4.86 out of 5 average rating, 321 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.

Guest favourite
A charming townhouse exterior is framed by neatly trimmed hedges, providing privacy. A light blue front door serves as a focal point, flanked by windows with shutters. Satellite dishes are mounted on the façade, enhancing the contemporary feel of the historic brick structure.
Townhouse
4.94 out of 5 average rating, 335 reviews

Fennel House. Charming house in Oakham town centre

The townhouse is located on a quiet residential one way street. Oakham has stunning historical architecture, i.e a castle, quaint independent shops, pubs and restaurants are moments from the door. A short walk from the railway station. It is ideal for couples or families. A short drive is Rutland Water and is the largest man made lake in Europe 26 miles circumference and hosts many outdoor pursuits such as walking, cycling and bird watching.

Top guest favourite
The exterior of a charming converted barn is set against a clear blue sky. A gravel driveway leads to the entrance, bordered by neatly trimmed hedges. The structure features a mix of brick and wood finishes, with a covered entryway and green landscaping enhancing the rural setting.
Barn
4.99 out of 5 average rating, 159 reviews

Beautiful Conversion in Rutland Countryside

Come and stay in our lovingly converted barn in the middle of the Rutland countryside. Perfect for a quiet get-away with lots of walking and cycling from the doorstep. Set in a 3 acre plot of our family home, you will have access to a private garden at the rear of the property plus our orchard should you wish to bring 1 small - medium sized dog with you. Unfortunately, the property is not suited to large dogs.

Top guest favourite
A modern wood-burning stove is positioned in the corner, with flames visible through the glass door. Below the stove, a compartment holds neatly stacked firewood. A woven basket is placed nearby, and a lamp on a side table illuminates the space softly.
Apartment
5 out of 5 average rating, 126 reviews

Mayfield - 1 bedroom annexe flat

Kick back and relax in this calm, stylish space. Private annexe flat with its own access. Open plan kitchen and living area. Separate dining area. 1 bedroom with zip link beds, can either be twin or superking. Bathroom with shower. Hallway. Access to washing machine, tumble dryer and clothes airer on request. Lockable storage for push bikes on request. Outside patio area.

Popular amenities for outdoor seating rentals in Oakham

Quick stats about holiday rentals with outdoor seating in Oakham

  • Total holiday rentals

    Explore 10 holiday rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at £60 per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Oakham holiday rentals include wifi access

  • 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!