Chalet vacation rentals in Weymouth and Portland District

4.94 out of 5 average rating, 124 reviews

The exterior of Wyvern Apartment features natural wooden cladding, complemented by a dark front door and multiple windows. A covered porch area includes a railing, providing an inviting entrance. The surrounding greenery adds a touch of nature to the setting.

Chalet in Somerset

Wyvern Apartment - Where your comfort matters

Wyvern Apartment is a newly converted studio apartment which is close to beautiful countryside and many great attractions. We have designed the apartment with our guests' comfort in mind and it has been ideally equipped for both business and pleasure guests. There is free parking, a flat screen smart TV, free unlimited WI-FI along with lots of other little touches to help make your stay as welcoming and convenient as possible. The apartment boasts a well equipped kitchen and walk-in shower room.

4.96 out of 5 average rating, 319 reviews

A nearly-new static caravan is presented with a spacious wraparound sundeck, enclosed by a white railing. The exterior features large windows that allow natural light, while a paved path leads to the parking area for two cars beside well-maintained grass.

Chalet in West Lulworth

Durdle Door & Lulworth Cove. Family/Dog friendly.

Our holiday home is located in Durdle Door Holiday Park near the famous stone arch of Durdle Door, a UNESCO World Heritage site. It's in a great position, being one of the closest homes to the beach access path, and boasts sea glimpses from the sun deck and living room window. Featuring all mod-cons it is a really comfortable home-from-home. The park is quiet and well-maintained with a shop, restaurant, bar and play-park. Lulworth Cove, along with its pubs and restaurants are a short walk away.

The exterior of the caravan is presented, featuring pale blue cladding and a spacious covered decking area with white railings. Large windows allow for ample natural light, and a clear blue sky adds to the seaside charm. The surrounding area includes lush greenery.

4.94 out of 5 average rating, 47 reviews

Our Plaice by the Sea

'Our Plaice by the Sea' is a 2 bedroom caravan, on the flagship Littlesea Haven holiday park. Our Plaice feels like a home from home, reminding us of a beach hut with its pale- blue cladding, decking out front and stunning views of Chesil Beach; it stands out, giving a relaxed seaside vibe. There’s plenty to do on-site with an indoor and outdoor pool, adventure golf, arcade, day and night entertainment (Haven passes to be purchased) fabulous coastal path walks and near to the Jurassic coastline.

A modern caravan is positioned on a spacious grassy plot. It features a large deck with white railing and a series of windows providing ample natural light. The exterior is clad in light-colored panels, and nearby caravans are visible in the background.

4.94 out of 5 average rating, 96 reviews

A luxurious modern 3-bedroom Swift Bordeaux

A luxurious modern 3-bedroom Swift Bordeaux Silver Prestige. This fabulous caravan is situated at Haven Littlesea Holiday Park in Weymouth in a spacious plot with views of the Fleet Lagoon and Chesil Beach. Sleeps up to 6 people. 1.5 bathrooms Linen and towels supplied. Parking spaces for 2 cars. Outside decking and seating area. Onsite restaurant, laundrette and local shop. For use of swimming pool, entertainment venue and booking activities you can purchase Play Passes from Haven

4.94 out of 5 average rating, 108 reviews

A sandy beach stretches across the foreground, with large stones placed sporadically. In the distance, a row of white chalets is visible against a backdrop of rolling hills under a cloudy sky.

Chalet in Puncknowle

Little Beach House on West Dorset’s Jurassic coast

Little Beach House is located in the unspoilt hamlet of West Bexington only 20 yards from Chesil beach which is on the Jurassic coast of West Dorset. It has uninterrupted views of the sea from the lounge and bedroom and has a very sunny aspect being a south-facing garden, outside it has a grassed back and front garden with private parking West Bexington has a hotel with restaurant and bar, it also has great food at the Club house restaurant, all within a short walking distance of the Chalet

5 out of 5 average rating, 12 reviews

The spacious mezzanine bedroom features a king-size bed with crisp cotton bedding and plush decorative pillows. A wooden bench draped with a soft throw sits at the foot of the bed. Nautical-inspired porthole windows and angled skylights allow natural light to enhance the serene decor.

Chalet in Uplyme

Luxury Riverlodge & Sauna by Lyme Regis

An idyllic, luxury stay & sauna. Immerse yourself in serenity at this chalet inspired lodge, built purely for rest & relaxation. This spacious stay is architecturally curated to inspire comfort and tranquillity. Gaze up at the high pitched ceilings and stunning glass fronted mezzanine floor. With unobstructed view of the glass fronted wood-burner, perfect for cosy evenings and peaceful mornings. Stroll the River nature trail effortlessly connecting you to the vibrant heart of Lyme Regis.

4.94 out of 5 average rating, 84 reviews

Chalet in Salwayash

Lavish Dorset countryside retreat

Escape to the idyllic countryside of Dorset and indulge in the ultimate retreat at The Drover. This luxurious holiday let, nestled near Bridport, offers a serene haven where modern comfort meets rustic charm. As you step into the spacious abode, you're greeted by an expansive open-plan layout that seamlessly combines a kitchen, dining area, and lounge. The heart of the home, the kitchen boasts sleek appliances including a dishwasher, fridge, freezer, oven, and a 5-ring induction hob, ...

A wooden deck features a neutral-toned table surrounded by matching chairs, providing a seating area with panoramic views of Swanage Bay. The coastline can be seen in the distance, framed by lush greenery and a clear blue sky.

4.93 out of 5 average rating, 283 reviews

Breathtaking sea views from this light, cosy lodge

Seascape is a bright, airy lodge down its own drive at the edge of Swanage Bay View. Adjoining Townsend Nature Reserve it enjoys utter tranquillity and spectacular views over the bay, as seen on 'A Place in the Sun'. With its tasteful modern furnishings, central heating and double glazing, Seascape is cosy in winter, while outside, the large deck offers a panoramic view all the way to Corfe Castle. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

Superhost

The exterior of The Duck House is depicted, showcasing a charming two-story chalet surrounded by lush greenery. The light yellow walls complement the natural landscape, while windows reflect the tranquil sky. The well-maintained lawn offers open space for relaxation and play.

Chalet in Whitchurch Canonicorum

4.88 out of 5 average rating, 226 reviews

The Duck House. A child/dog friendly rural chalet

The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.

The exterior of the log cabin is presented, featuring a facade with stacked wooden logs and large glass doors. Lush green grass surrounds the structure, complemented by leafy plants in pots. The scene captures a serene and natural ambiance, set against a backdrop of trees.

4.91 out of 5 average rating, 198 reviews

Boutique Log Cabin Hideaway near the Coast

Escape to a cosy garden log cabin tucked among trees, with its own private entrance. Hidden from the road and screened by mature eucalyptus, it’s just 10 minutes from Bournemouth’s 7-mile stretch of sandy beaches, Christchurch’s riverside attractions, and the New Forest. It’s only minutes to a local pub/restaurant. Perfect for two guests, friends or couples, the cabin offers a relaxing retreat close to everything, beaches, nature, and great local food spots.

5 out of 5 average rating, 18 reviews

A spacious living area showcases comfortable seating with a light blue sofa and a wooden coffee table. Large glass doors open to a balcony with sea views, while curtains frame the windows. Dining arrangements are visible with a table set for several, enhancing the welcoming ambiance.

Chalet in Ringstead

Kingfisher - Creek Caravan Park Ringstead

Welcome to Kingfisher, a spacious lodge at Ringstead Bay that offers the perfect blend of comfort and seaside charm. With plenty of room to relax, this lodge is ideal for long stays by the beach. Take in the stunning sea views from the balcony, explore nearby coastal trails, or visit local spots like Weymouth and Durdle Door. Our friendly staff is on hand to ensure a memorable and relaxing stay.

Superhost

A covered deck area extends from the chalet, featuring a picnic table and two chairs, offering a space to enjoy the coastal views. A wooden fence provides privacy, while the backdrop includes additional chalets and greenery, under a partly cloudy sky.