Vacation rentals in Skegness

4.94 out of 5 average rating, 225 reviews

Fairytale Cottage in a Beautiful Garden

Step into this dreamy cottage, secluded within its rambling sunny gardens with ample seating to enjoy the view. Delight and relax in its thoughtfully curated interior. Wake up refreshed within pretty bedrooms tucked into the eaves, and look out over the garden with constant soundtrack of birdsong. Relax by the log burner, or fire up the BBQ after you explore the walks which extends beyond the country lane, even if you only venture as far as the delicious cosy gastro pub, cafes & farm shop nearby

An outdoor deck area features comfortable seating with dark wicker furniture, providing views of sandy dunes and the sea. A glass balustrade surrounds the space, allowing unobstructed sightlines of the coastal landscape. Natural light fills the area, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 279 reviews

Beach-front cottage. Sea view from every room.

Anderby Creek was voted one of the UK's best undiscovered beaches by AOL, The Times & The Telegraph. The house has simply beautiful views of the beach, sea and sand dunes with extensive decking surrounded by glass balustrade where you can sit outside and enjoy the sea air. It's a family home, fully centrally heated and comfortable. Expect mismatched crockery & imperfection! It's a steep drive up to the house & steps to the beach (although you can go around the drive way) so not suitable for all

4.97 out of 5 average rating, 732 reviews

Loft

The Loft at Peace Haven near Woodhall Spa

Self contained peaceful loft studio with far reaching views over farm fields & Lincoln Cathedral. Access via private stairs. Parking space. 5 minutes from the inland resort of Woodhall Spa. Private oak balcony with seating area & beautiful views across countryside. Hotel designed King size bed (can be split into twin beds) (orthopaedic mattress). Tea, coffee & toast facilities only (tea/coffee/cereals/porridge/snacks & milk included). Fridge. En suite shower room. Table & chairs. Tv & radio.

A modern glamping pod features a unique arched roof and a wooden deck with slatted railing. The exterior showcases a brown shingle design, set against a softly lit sky. The surrounding grassy area provides a natural setting for relaxation.

4.98 out of 5 average rating, 128 reviews

Lovely Glamping Pod with Hot Tub

Experience luxury and comfort in our spacious glamping pods at Pepperwood Pods. The pod is fully centrally heated and features an ensuite bathroom, a well-equipped kitchen with a coffee machine, dishwasher, cooking utensils, and condiments. Relax in the double bed or on the sofa bed, and enjoy entertainment with the TV and WiFi. The unique glass end wall entrance offers stunning views and natural light. Unwind in your private hot tub or lounge around the fire pit for a serene evening.

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.

4.95 out of 5 average rating, 113 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.

The lodge's exterior showcases a modern wooden design with a sloped roof. Large glass doors reflect the warm glow of the sunset, while a stone pathway leads to a seated area with wooden chairs and tables on the manicured lawn, surrounded by greenery.

4.99 out of 5 average rating, 219 reviews

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

Located at Wren Farm, our brand new to 2023 luxury lodge 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.

4.97 out of 5 average rating, 250 reviews

A spacious indoor heated pool area features a serene swimming pool surrounded by artificial grass. Expansive windows allow natural light to flood the room, framing views of the outdoor landscape. Comfortable seating areas are placed nearby, creating a relaxed atmosphere.

Barn

Luxury Annex beside the River Bain Nr Woodhall Spa

A most beautiful luxury annex to the main residence , with an indoor heated luxury swimming pool and 2 person sauna infrared.The property is set on the River Bain ,with open views to the Bain valley. . The pretty village of Kirkby on Bain is just 600 yards away. The Ebbington Arms is a wonderful public house which is well renowned for its excellent food. The Edwardian inland resort of Woodhall Spa is just 4 miles away here you find fantastic restaurants, shops and wonderful walks.

A charming brick structure is visible, set amidst an open landscape. Lush hedges and a gravel driveway frame the entrance, while a modest white door offers access. The sloped roof and chimney add character, complemented by a serene sky with scattered clouds.

4.96 out of 5 average rating, 137 reviews

Retreat to a former Chapel, relax in privacy.

With unspoilt views over countryside, our former Chapel on the Lincolnshire Wolds doorstep offers the perfect place to enjoy a memorable relaxing stay. Visit all that this County has to offer, including miles of lovely beaches, followed by snug winter evenings in front of a Log Burner, or warm summer evenings relaxing on the Patio, perhaps observing the wildlife. There is a myriad of tracks and paths around for walkers and cyclists alike. We offer comfort with a homely feel.

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.

4.99 out of 5 average rating, 316 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.

A scenic outdoor area is highlighted with a picnic table and a firepit, overlooking the tranquil lake. Nearby, a black storage unit is present, and several cabins are visible in the background against a clear blue sky.

4.91 out of 5 average rating, 1,027 reviews

Adults only cabin with double bed with Hot Tub

In the middle of nowhere but only 8 miles from Boston town, 12 miles from Skegness Beach and 3 miles from the sea/coast boasting award winning RSPB nature reserves and marshes. 28 cabins on a 3 acre lake. Pet and children are more than welcome.We have an orchard for you to walk around and even a dog agility area (Bookable). Double cabins with Finnish hot tubs (Adults only, charges apply for wood/firelighters). Twin cabins pet/child friendly. Double cabins pet/child friendly.

The single-storey barn conversion is showcased, featuring light-colored exteriors and a red-tiled roof. A wooden fence surrounds the property, complementing the manicured lawn. Windows allow for natural light, providing a welcoming exterior that connects with the surrounding landscape.

4.98 out of 5 average rating, 112 reviews

Mollie’s Cottage

Mollie’s Cottage is a single-storey barn conversion located just a 10-minute walk from the sandy beach at Chapel Point. There is an enclosed garden, perfect for relaxing in after a busy days’ adventure. It makes a great base for a family holiday at the east coast. Outdoor pursuits nearby include good walks and cycle routes. Some areas of the beach are dog friendly. Beach ¾ mile. Shop, pub and restaurant ½ mile. One dog free per booking. 2 maximum (2nd dog chargeable)

4.95 out of 5 average rating, 153 reviews

The exterior of a uniquely shaped wooden pod is depicted, featuring a sloping roof and a large arched window. The door is made of natural wood and is flanked by potted plants. The pod is surrounded by greenery, including shrubs and flowering plants.

Place to stay

♥cosy; parking; garden; rural cycle/walks+more

Idyllic, rustic, quiet self contained private 1 bed Pod in the meadow style garden of a Victorian house on the edge of the Lincolnshire Wolds and also within walking distance of Horncastle market place, shops and amenities. Private entrance with self check in and own parking space, use of large garden, galley kitchen (with sink, small fridge, microwave), dining area and bedroom (double bed) with en-suite suitable for 1-2 adults only (sorry no children or pets).

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Skegness vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Skegness

4.93 out of 5 average rating, 27 reviews

The bright kitchen and living area feature a spacious corner sofa and a dining table set for four. Natural light enters through large windows, highlighting modern appliances and a cozy decor. A round area rug adds warmth to the hardwood floor.

Condo

Modern 2 bedroom holiday apartment private parking

A stylish living area features a black television mounted on a light gray wall. Two sofas, one black and one yellow, are arranged around a circular coffee table. A patterned area rug adds color to the space, complemented by natural light from large windows with blinds.

4.97 out of 5 average rating, 29 reviews

Sea Breeze House

4.98 out of 5 average rating, 83 reviews

Bungalow

Skegness, peaceful, bungalow, king bed, parking.

4.89 out of 5 average rating, 53 reviews

A charming log-house is set in a wooded area, featuring a dark exterior with a sloped roof. A welcoming porch with wooden railing is visible, and a vintage lamp post adds to the ambiance. Autumn leaves cover the ground, creating a peaceful atmosphere.

Treehouse

Narnia - a picture-perfect private woodland escape

Superhost

The exterior of a newly refurbished house is displayed, featuring a bright white facade with distinct lighting fixtures by the entrance. Large windows allow natural light into the interior, while a gravel driveway is visible, surrounded by wooden fencing that offers privacy.

4.85 out of 5 average rating, 34 reviews

Clarendon House - Hot Tub

5 out of 5 average rating, 21 reviews

An open plan kitchen and lounge area features a corner sofa, positioned to face a 70-inch smart TV on the wall. Skylights allow natural light to illuminate the space, highlighting a glass dining table with seating for six beside the kitchen with integrated appliances.

Apartment

The Loft

A large modern hot tub is positioned under a rustic gazebo, surrounded by decorative hats and lights. Rattan furniture and coffee tables create a relaxed seating area, and a dining table for ten is visible, enhancing the inviting outdoor atmosphere.

4.99 out of 5 average rating, 70 reviews

4 bed Cottage with Hot Tub sleeps 12 pet friendly

The exterior of the property features a two-story design with a welcoming entrance. A balcony extends from the upper level, providing outdoor space. The driveway leads to a secure entrance, while plants are positioned along the perimeter, offering a touch of greenery.