Pet-friendly holiday rentals in Oakham

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Top-rated pet-friendly home rentals in Oakham

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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.
Condo in Tilton on the Hill
4.9 out of 5 average rating, 165 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.

Guest favourite
A charming brick exterior of the accommodation is visible, featuring a white door framed by several windows. In the foreground, a peacock displays its colorful feathers amidst flower pots filled with blooming yellow daffodils. The surrounding area is paved and lined with greenery.
Guesthouse in Burton on the Wolds
4.89 out of 5 average rating, 847 reviews

Quiet cottage close to Prestwold & Loughborough

This is a self-contained place next to the main house. The location is at end of a farm track in quiet secluded hamlet - Burton Bandalls (on the B676, Loughborough Rd between Prestwold & Cotes). 5 min drive / 20 min walk to Prestwold Hall. 5 min drive to Loughborough Railway station. 10 min drive to Loughborough University. 10 min drive to Great Central Steam Railway. 25 mins to East Midlands airport, 30 mins to Leicester, 30 mins to Nottingham, 45 mins to NEC and 60 mins to Birmingham.

Top Guest favourite
Townhouse in Manton
4.99 out of 5 average rating, 157 reviews

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. The fenced garden has a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included

Guest favourite
A stone cottage features a sloping roof and large glass doors opening to the garden. A wooden pergola, supported by beams, adorns the outdoor seating area. Lush greenery and lavender line the property, enhancing the peaceful countryside setting.
Tiny home in Ketton
4.82 out of 5 average rating, 106 reviews

Beautiful and Quaint Converted Stable in Rutland

This Grade-2 Listed, self-contained, dog-friendly cottage is the perfect hideaway for a couple looking to enjoy the beautiful Rutland countryside. Ketton is only a few minutes drive from the beautiful town of Stamford, or Rutland Water with its stunning views and local Ospreys. Oakham is also a short drive away. There's a Camra award-winning pub a few minutes walk away and plenty of circular walks in the surrounding countryside, from the accommodation or further afield, to work up a thirst.

Top Guest favourite
A view from an open window reveals a green meadow, where sheep graze peacefully. A stone wall borders the edge of the field, with trees and distant hills visible against the blue sky. Natural light filters softly into the space.
Barn in Drayton
4.93 out of 5 average rating, 108 reviews

Luxury apartment with outstanding views

We created a self catering studio apartment from our hay loft during the lockdown of 2020. In the heart of the Welland Valley in Leicestershire there are are wonderful views up the hill to Nevill Holt (home of the Nevill Holt Opera Festival) and from the sofa you will be able to watch the sun setting behind the hill. Many miles of footpaths on the doorstep. There is a heated pool open May-Sept and a tennis court. Please ask us regarding access. Check out our guidebook for things to do

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
4.99 out of 5 average rating, 172 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.

Guest favourite
A spacious bedroom is highlighted by a dark green accent wall featuring two framed animal prints. The large bed is topped with a textured blanket and neatly arranged towels. Soft lighting from bedside tables creates a calming ambiance in this inviting space.
Condo in Uppingham
4.91 out of 5 average rating, 179 reviews

Comfy Modern APT - Sleeps 4

Located in the centre of the Historic Market Town of Uppingham. Based in is heart of the small county of Rutland. This apartment is a stones throw away to the gorgeous town centre, with markets every Friday, great places to eat and drink and some really cute little shops. A quick 10 minute drive to another Market Town of Oakham and not far from Rutland Water where you can enjoy some beautiful scenic walks. The apartment offers an allocated parking space and communal paved garden.

Top Guest favourite
A rustic shepherd's hut is nestled amidst greenery, framed by willow trees. A grassy area with outdoor seating is visible in front, alongside a wood-burning stove contributing to a cozy atmosphere. Smoke gently rises into the air, suggesting warmth and comfort.
Shepherd’s hut in North Witham
4.98 out of 5 average rating, 253 reviews

Little Oaks at Hillview

Beautiful, Luxurious, Home from Home Shepherds Hut. Nestling in its own fenced spinney with 300 year old Ash and Oaks trees around you, Little Oaks is rural, isolated and private. You can enjoy the wood fired hot tub, fire pit, BBQ or Pizza oven with only the sheep, goats, horses and chickens on our farm watching. Looking out over rolling countryside, our home built hut is cosy, beautifully appointed, and built to an exacting specification, somewhere we would love to stay!

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 in Manton
4.96 out of 5 average rating, 370 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 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
4.93 out of 5 average rating, 383 reviews

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.

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 in Whissendine
4.99 out of 5 average rating, 156 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
The exterior of a charming 19th century barn is showcased, featuring a stone facade adorned with climbing wisteria. Two wooden doors frame the entrance, complemented by two symmetrical windows above. A gravel area leads up to the building, enhancing the quaint rural aesthetic.
Guesthouse in Clipsham
4.94 out of 5 average rating, 121 reviews

Spacious 2 bed barn conversion in Rutland

This 19th century converted barn offers spacious and cosy accomodation and is situated next to the renowned award winning Olive Branch restaurant and is a quick 15 minute drive to central Stamford and Burghley House. Church Barn is a 6 minute drive to the sublime wedding venue of Holywell Hall. Church Barn is an old building with imperfections to be expected. Pets by prior agreement

Popular amenities for Oakham pet-friendly home rentals

Quick stats about holiday rentals that are pet-friendly in Oakham

  • Total holiday rentals

    Explore 10 holiday rentals in Oakham

  • Nightly prices starting at

    Oakham holiday rentals start at $103 NZD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Oakham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oakham rentals

  • 4.8 Average rating

    Oakham stays are highly rated by guests—averaging 4.8 out of 5!

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