Pet-friendly holiday rentals in Oakham

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Top-rated pet-friendly home rentals in Oakham

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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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.
Guest house
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
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
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
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, 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.

Top guest favourite
A shepherd's hut is set in a tranquil orchard, surrounded by blooming flowers. A small outdoor seating area with a table and chairs is visible in front of the hut, which has large windows allowing natural light into the interior.
Shepherd’s hut
4.98 out of 5 average rating, 186 reviews

Drift View Shepherds Hut

Welcome to Drift View, lovingly designed and built by ourselves and set on our family farm close to the Rutland/Leicestershire border. The hut is positioned in a private and secluded orchard, next to the farmyard and offers stunning views of the rural landscape. You can experience the peace and tranquillity the location provides whilst enjoying the luxury of the shepherds hut which has an en-suite with shower, fully equipped kitchen, double bed and both indoor/outdoor dining areas.

Top guest favourite
The image showcases the exterior of a Victorian cottage featuring a combination of warm brick tones. Two large windows are visible on the front, providing light to the interior, while a solid black door is centrally positioned. The façade exudes a classic charm.
Home
5 out of 5 average rating, 113 reviews

Character cottage in Stamford

This peaceful, recently renovated Victorian cottage, five minutes walk from Burghley park and Stamford high street, has a sunny patio courtyard and private off street parking. It has been decorated in bold Farrow & Ball colours and William Morris wallpaper, with new fittings and furniture throughout. Situated just up the hill from the Meadows, River Welland and famous George Hotel, there are extensive views across the historic rooftops of Stamford from the bedroom windows.

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
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
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 modern two-story lodge showcases a clean exterior with pitched roofs and large glass doors. The setting features a gravel area leading to an inviting outdoor space, surrounded by trees and open countryside, reflecting a serene atmosphere.
Home
4.99 out of 5 average rating, 128 reviews

Cherry Lap Lodge:Luxury hot tub/treehouse/ getaway

Set in 14 acres of beautiful northamptonshire countryside, Cherry lap lodge can be found on the grounds of a large farm. Escape and unplug in our luxury farm lodge. Nestled in a quiet location in the heart of our farm. Our lodge was previously an annex now hand crafted into a modern, luxury hot tub retreat. When it’s sunny an outdoor kitchen, bbq, hot tub and treehouse lookout onto the sheep field’s. Only 1 hour from London Insta: @Cherrylaplodge

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
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
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.
Guest house
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 £45 per night before taxes and fees

  • Verified guest reviews

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  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Oakham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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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