Family-friendly holiday rentals in Old Leake

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Top-rated family-friendly rentals in Old Leake

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

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Guest favourite
Cabin in Boston Lincolnshire
4.91 out of 5 average rating, 1,300 reviews

Adults Only Cabin With Log Burning Hot Tub

Lakeside Fishing Retreats offers peaceful lakeside stays in the middle of nowhere, yet perfectly placed. Just 8 miles from Boston town, 12 miles from Skegness Beach and 3 miles from the coast with award-winning RSPB marshes. We have 28 Cabins set on a 3 acre lake: - Adult Only Double Cabin with Log Burning Hot Tub (Pet friendly/Non Pet friendly Cabins) - Standard Double (Child/Pet friendly/Non Pet friendly Cabins). - Twin Cabin (Child/Pet friendly) You can also enjoy our onsite Pizza Shed & Bar!

Top Guest favourite
The exterior of a charming brick annex is visible, featuring distinctive arched windows framed by greenery. The facade is adorned with hanging flower baskets, adding a touch of colour. A gravel driveway offers ample parking space, contributing to a welcoming entrance.
Home in Boston
4.92 out of 5 average rating, 244 reviews

The Annex @ Ormiston House

*MAY/JUNE OFFER* £69p/n The Annex@Ormiston offers unique accommodation for up to 4 guests, in a self-contained building adjacent to our family home. It has ample private parking, a secure entrance, a private courtyard & access to a large garden. Downstairs, there's a kingsize bedroom, shower room, lounge and fully equipped kitchen. Upstairs, an additional bedroom contains one or two single beds. The property is a 10 minute walk from the town centre and less than a mile from Pilgrim Hospital.

Top Guest favourite
The light-filled guestroom displays a spacious bed adorned with a soft throw, alongside two cozy wingback chairs. A large window offers views of the garden, while a wall-mounted television provides entertainment. French doors lead to the private outdoor space, enhancing the inviting atmosphere.
Guest suite in Friskney
4.96 out of 5 average rating, 103 reviews

Cosy guest room, pet friendly with outdoor space

Named after our resident Robins, Robins Nest Guestroom is our self-contained accommodation offering a peaceful getaway for comfort and rest. Relax in your own private garden or explore the nearby attractions. Furthermore, we know that your fur babies are an important part of your family. We are pleased to welcome well-behaved pups. Together you can explore dog friendly beaches and Nature trails. Conveniently close to Skegness and Boston. Book your stay today. We look forward to welcoming you.

Top Guest favourite
Cottage in Old Leake
4.96 out of 5 average rating, 193 reviews

The Scholars

A light open planned living space, with fitted kitchen, washing machine and fridge and cooker. Two comfy sofas, one of which is a bed settee, TV and Wi-fi . A dining table and chairs, complete this lovely holiday accommodation. Two large airy double bedrooms, with ample storage. A lovely walk in shower, complete with heated luxury towel rail. USB charging points throughout the property. It will be deep cleaned between guests , is self contained to ensure peace of mind with social distancing

Top Guest favourite
An open-plan living area features two large sofas, one leather, and one plush, arranged around a wooden coffee table on a traditional patterned rug. A large chandelier hangs from the ceiling, illuminating the space, while a smart TV is positioned near the opposite wall.
Home in Wainfleet All Saints
4.96 out of 5 average rating, 142 reviews

The Lodge at Thorpe House

Luxury converted barn in beautiful rural Lincolnshire. The Lodge at Thorpe House is a stunning, totally unique, spacious, newly refurbished, well equipped Lodge, bursting with character combining beautiful antique furniture featuring a stunning 19th Century 5 foot French Chateau Ballroom Chandelier and new fully fitted open plan kitchen, dining and living area. Oak flooring. A five bar gate leads to gravelled parking and a pretty ornate archway leads to a totally private enclosed garden.

Top Guest favourite
Vibrant pink coneflowers fill the foreground, showcasing their large petals and distinctive center. Behind them, a cozy green Shepherds Hut can be seen, nestled within a well-tended garden. Lush greenery and flowering plants frame the scene under a bright blue sky.
Shepherd’s hut in Lincolnshire
4.99 out of 5 average rating, 122 reviews

Fully equipped, quirky, comfortable Shepherds Hut.

Nestled in the AONB Lincolnshire Wolds at the heart of Tennyson country this cosy, comfortable, well equipped Shepherds Hut is the ideal getaway for 1/2 adults craving unspoiled countryside and a place to be quiet, retreat and to recharge. The Hut is in a peaceful country garden with its own fenced in area for privacy. Enjoy views over fields and hills beyond. Zero light pollution, so starry skies. Nominated for top 10 self-catering accommodation 2024 and 2025 by Lincolnshire Life Mag.

Top Guest favourite
A dining area features a long table set for a meal, surrounded by white chairs. Above, a large chandelier made of antlers provides lighting. Vibrant artwork depicting birds adorns the walls, complementing the soft furnishings and natural light flowing in from the window.
Cottage in Lincolnshire
4.99 out of 5 average rating, 244 reviews

One bedroom boutique cottage NEW refurb with views

The Coach House at The Laurels Cottages. Relax in this calm stylish space. A newly refurbished one bedroom cottage in the picturesque village of East Keal Close to Horncastle, Skegness & all the gorgeous market towns. local pubs amazing walks & cycle paths and antique shops. Bring your dog max 2 feel free to roam in our paddock . Footpaths on your door stop Amazing out door patio it's a sun trap with sunloungers, barbecue. All new furniture. Breakfast supplies will also be left.

Top Guest favourite
A modern lodge features a distinctive sloped roof made of wooden shingles. Large glass doors provide access to a spacious outdoor area, complemented by a stone pathway. Natural surroundings with green grass and trees can be seen in the background, reflecting a serene atmosphere.
Cabin in Hogsthorpe
4.99 out of 5 average rating, 146 reviews

Robin Lodge W/ Alpacas, Goats & Sheep | Wren Farm

Located at Wren Farm, our brand new to 2023 luxury lodges situated besides the alpaca fields, with Wren Farm Desserts cafe on site. Also near beaches, Skegness, Chapel, Mablethorpe, etc. We are dog friendly! Fully stocked (cutlery) Has 1 double bed and a sofa bed that sleeps 2. Private bathroom with shower. Surrounded by green fields, beautiful animals and excellent food! Add ons available on request - Ploughman's Grazing Box, Breakfast Boxes. Alpaca trekking also available.

Top Guest favourite
A scenic view of the property is captured, showcasing a well-maintained garden with lush greenery and a pond. The charming buildings, framed by tall trees, are situated against a backdrop of blue sky with scattered clouds, creating a serene atmosphere.
Guest suite in Goulceby
4.99 out of 5 average rating, 128 reviews

The Beeches, Goulceby (Willow)

You’ll love this charming property, set on an equestrian yard in the beautiful Lincolnshire Wolds. A picturesque and peaceful location, with immediate access to walking trails (including The Viking Way), yet only a short drive away from popular attractions including Cadwell Park, local market towns and the Lincolnshire Coast. Goulceby is a quiet village with a popular pub five minutes walk from the property. We have ample parking for vehicles, including room for vehicle trailers.

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
4.99 out of 5 average rating, 364 reviews

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.

Top Guest favourite
The exterior of a semi-detached cottage displays a whitewashed facade and a traditional green front door. Two brick chimneys rise from a sloped roof, while windows with white frames provide symmetry across the front. A sign above the doorway details the establishment's historical significance.
Home in Stickney
4.87 out of 5 average rating, 535 reviews

Honeysuckle Cottage, 2 bedroom cottage

A historically significant building,Honeysuckle Cottage has been beautifully restored. The front has been kept with the original front door but actually it is semi detached. It has exposed ceiling beams and natural wood furniture. The vintage decor adds to the homely feel of this two-bed cottage, perfectly equipped for a couple or small family to stay. Easy to access by car or bus, this cottage provides the escape of the countryside with the convenience of a large village.

Guest favourite
The caravan is set on a grassy area, featuring a spacious deck. Surrounding trees provide a natural backdrop, while a gravel pathway leads to the entrance. The exterior is light-colored, with multiple windows allowing ample natural light.
Campervan/RV in Stickford
4.95 out of 5 average rating, 550 reviews

Static Caravan on private garden

Situated in Stickford at the base of the Lincolnshire Wolds this is a great place to explore Lincolnshire. Wonderful dog friendly beaches 25 minutes away with plenty of walking and fishing locally. The historic city of Lincoln is 45 minutes, and the seaside town of Skegness is 15 miles away. The caravan is situated in our garden which has a large pond so children must be supervised at all times. We have 3 dogs, and free ranging chickens so visiting dogs must be on leads.

Popular amenities for Old Leake family-friendly rentals