House holiday rentals in Skegness

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Top-rated house rentals in Skegness

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Top guest favourite
The image captures a view of Boston Stump, a prominent church tower, rising above the landscape against a clear blue sky. Surrounding trees and a grassy area add a natural touch, while a decorative fence frames part of the scene on the right.
Home
4.93 out of 5 average rating, 101 reviews

A lovely 2 bedroomed residential home in Boston

A perfect place to stay, this recently renovated two bedroomed Victorian terraced house is in a delightful setting on the bank of the river Witham with stunning views of Boston Stump. Guests benefit from being in a great location, within a 5 minute walk you are in Boston town centre where you will find historic buildings, great shops, pubs & restaurants. Boston train station and a large ASDA supermarket are both within a 10 minute walk. This home from home also has its own private parking space.

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
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 exterior of a charming cottage is framed by blooming flowers and lush greenery. A gravel driveway leads up to the home, which features a mix of brick and wooden elements, with a gently sloped roof and inviting windows. Nearby, pots of vibrant plants are positioned along the pathway.
Home
4.97 out of 5 average rating, 149 reviews

Cosy Hazel Nook option of Undercover Hot tub

A charming, unique, cosy little home from home with everything you could need for a perfect break away. With additional OPTION of an Undercover Hot tub. We border Sandringham Estate & Houghton Hall with their gorgeous woodland Walks. We are central to many of the beaches, Great for you and your furry friend. We have Bircham Windmill with its fresh bakery & tearoom. Bircham store & cafe or dine at our local Pub. A fabulous base to then go out and explore. Come Relax & Enjoy North Norfolk. X

Guest favourite
An open-plan living area features a cozy seating arrangement with a light grey sofa and accent chairs. Natural light floods through large windows and a skylight, illuminating the well-equipped kitchen in the background. A wooden dining table with chairs and a small decorative rug enhance the space.
Home
4.97 out of 5 average rating, 153 reviews

Seven Spires Barn with Private Hot Tub and Sauna

Seven Spires Barn is the perfect getaway for two, where traditional features meet modern luxury. Guests can relax, feel restored and explore the best that Lincolnshire has to offer. The barn features a freestanding roll top bath and woodburning stove. Outside guests can enjoy a private enclosed garden with hot tub and sauna. With special touches including luxury Bramley toiletries and complimentary toweling robes. Just 10 minutes from Woodhall Spa and 25 minutes from Historic Lincoln.

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
4.96 out of 5 average rating, 140 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.

Guest favourite
Home
4.96 out of 5 average rating, 192 reviews

Beautiful, Spacious, 3 bed 2 bath , near Lincoln

Wayside is a beautiful, period house in a rural village setting 15 minutes drive to Lincoln city centre. It’s an ideal base for Lincolnshire's attractions and events. There is a kitchen , utility ,dining room , orangery and lounge , two kingside bedrooms and bathroom and a downstairs king size bedroom with en suite shower. There is a pretty garden and local woodland and country walks . Wayside is ideal for friends and families wanting a luxurious space to share and make memories.

Guest favourite
A white-rendered cottage is set amidst lush greenery, featuring a welcoming archway at the entrance. Well-maintained hedges line the pathway leading to the front door, while the sun casts a gentle light, illuminating the exterior and garden area.
Home
4.93 out of 5 average rating, 155 reviews

Luxury Country Cottage, The Old Gatehouse

🏡Luxurious Countryside Cottage, with Cosy dining, large corner sofa & brand new kitchen. Ideal for walkers, cyclists, families and dogs 🏡 The Old Gatehouse has been fully renovated to offer a beautiful holiday retreat 🌳Set in a lovely Lincolnshire Wolds village, beautiful walks on the door step to the Ancient Woods and picturesque waterside walks to the pub. ✅ 5 mins to Louth, which is a thriving market town with an abundance of restaurants and shops. 🏖️15 mins to the beach

Guest favourite
A well-lit living area is viewed through an open doorway, featuring a grey sofa adorned with cushions. A coffee table rests on a soft rug, positioned under large windows that frame a green, tree-lined view.
Home
4.96 out of 5 average rating, 120 reviews

Woodhaven Stays

If you are looking for a place to relax then look no further! Whether it be a couples weekend away or a holiday for the full family, Woodhaven Stays is the perfect location. Our beautiful house sleeps 6 people and don't forget we are pet friendly ! This spacious home provides all the comforts you need when you are away from home, a spacious living and dining area, stunning kitchen, utility and sitting area. Of course we cannot forget the scenic garden with hot tub and BBQ.

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
4.87 out of 5 average rating, 534 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.

Top guest favourite
A spacious living area is highlighted by a brown leather sofa and a king size bed featuring yellow bedding. Dark wood paneling and decor create a cozy ambiance, while large windows are dressed with patterned curtains, allowing natural light to enter the room.
Home
4.95 out of 5 average rating, 153 reviews

Luxurious & unique coastal haven

Situated in Snettisham, Hammond’s Courtyard offers peace and tranquility, ideally located to explore the beaches. Snettisham is a stone throw away from the Royal residence, Sandringham House and RSPB Snettisham. The property is suitable for up to 2 adults and 2 children under 12 years old. Hammond’s Courtyard is the perfect place to stay with a luxurious, romantic and spacious living area with a private oriental courtyard, encompassing all your needs for a relaxing stay.

Guest favourite
The exterior of a charming red-brick building is displayed, featuring large arched windows and an intricate façade. A wrought-iron fence encloses the property, highlighting its unique architectural style. The entrance is framed by columns, providing an inviting perspective of this distinctive location.
Home
4.94 out of 5 average rating, 253 reviews

1 Old Drill Hall - A little piece of History

This unique place has a style all its own. Centrally located to all amenities in the historic market town of Alford, and only a short drive to Lincolnshire’s east coastline beaches and villages. Whether you want a base from which to visit the beautiful local beaches, explore the countryside or visit some of the many local attractions, this fully equipped 2 bedroom home has all you need for a relaxing break.

Guest favourite
An indoor heated swimming pool is framed by large windows allowing natural light to fill the space. Exposed wooden beams add an architectural feature overhead, while a relaxed seating area is situated nearby, offering a view of the tranquil pool waters.
Home
4.9 out of 5 average rating, 331 reviews

Private Indoor Pool | Countryside Retreat

The Barns Haceby: Escape to your own private countryside retreat with exclusive access to a heated indoor swimming pool — perfect for couples, families, or small groups looking to relax and unwind. Set within peaceful gated grounds in the Lincolnshire countryside, this beautifully converted barn offers privacy, comfort, and a calm setting to switch off and enjoy time together.

Popular amenities for house rentals in Skegness

Quick stats about house rentals in Skegness

  • Total holiday rentals

    Explore 30 holiday rentals in Skegness

  • Nightly prices starting at

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

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Wifi availability

    30 of Skegness holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Skegness rentals

  • 4.7 Average rating

    Skegness stays receive an average rating of 4.7 out of 5 from guests

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